Regioselective Synthesis of Mono- and Dispiropyrazoline Derivatives via 1,3-dipolar Cycloaddition with Nitrilimines

The 1,3-dipolar cycloaddition reaction of (E,E)-1,3-bis(arylidene)indan-2-one with diarylnitrilimines, generated in situ via dehydrohalogenation of the corresponding hydrazonoyl chlorides , affords predominantly monospiropyrazolines and as a mixture of diastereoisomers. Also dispiropyrazolines are formed in moderate yields. The structure and stereochemistry of cycloadducts were confirmed by 1H and 13C-NMR spectroscopy, elemental analyses data, and single-crystal X-ray diffraction studies of and .

Front Cover: Facile Synthesis and Self‐Assembly of Zinc (2‐Diethoxyphosphorylethynyl)porphyrins (Eur. J. Inorg. Chem. 10/2019)

Synthesis of highly substituted spiropyrrolidines via 1, 3-dipolar cycloaddition reaction of N-metalated azomethine ylides. A new access to spiropyrroline derivatives

1,3-dipolar cycloaddition of (E)-arylidene-(2H)-indanones 1 (Ar = Ph, p-MeC6H4, p-MeOC6H4, p-ClC6H4) and (E)-2-arylidene-(2H)-tetralones 2 (Ar = Ph, p-MeC6H4, p-MeOC6H4, p-ClC6H4) to N-metalated azomethine ylides 3 generated from methyl N-arylideneglycinate in the presence of silver acetate produces in good yields novel spiro[3,5-(diaryl)-2-carbomethoxypyrrolidine-4:2’-indanones] 4 and spiro[3,5-(diaryl)-2-carbomethoxypyrrolidine-4:2’-tetral-1-ones] 5. The cycloaddition proceeds in regio- and stereoselective manner (100%) at room temperature to afford respectively the syn-endo cycloadducts 4 and 5 via metallo-azomethine ylides. The regio- and stereochemistry of the spiranic adducts has been…

P-Chirogenic Triazole-Based Phosphine: Synthesis, Coordination Chemistry, and Asymmetric Catalysis

Cyclam-functionalized silica-modified electrodes for selective determination of Cu(II)

Cyclam derivatives have been grafted via 1, 2 or 4 silylated arms to the surface of mesoporous silica and the resulting materials have been incorporated into carbon paste electrodes and applied to the preconcentration electroanalysis of Cu(II). Sensitive and selective detection of the target analyte was achieved owing to the attractive binding properties of this macrocyclic ligand towards Cu(II) species. Various parameters likely to affect the preconcentration and detection steps have been studied, including pH of the accumulation medium, composition of the detection solution, structure and composition of the adsorbent, accumulation time, or presence of potentially interfering species. In p…

Towards sensory Langmuir monolayers consisting of macrocyclic pentaaminoanthraquinone

A pentaazamacrocycle incorporating an intracyclic anthraquinone fragment (PENTAQ) was synthesized with the aim of forming metal-responsive Langmuir monolayers. PENTAQ allows a good discrimination by naked eye of copper ions in methanol–water solutions (50 : 50 v/v). Spectrophotometric investigations of the protonation and Cu2+ binding properties of PENTAQ were undertaken in order to gain a deeper insight into the pH-dependent speciation as well as the color changing process. PENTAQ monolayers at air/water and air/methanol–water interfaces were prepared according to the Langmuir procedure. The structure of the monolayers can be tuned by varying the pH of the aqueous subphase, since it was fo…

Reactivity of CuI and CuBr toward Et2S: a reinvestigation on the self-assembly of luminescent copper(I) coordination polymers.

CuI reacts with SEt(2) in hexane to afford the known strongly luminescent 1D coordination polymer [(Et(2)S)(3){Cu(4)(mu(3)-I)(4)}](n) (1). Its X-ray structure has been redetermined at 115, 235, and 275 K in order to address the behavior of the cluster-centered emission and is built upon Cu(4)(mu(3)-I)(4) cubane-like clusters as secondary building units (SBUs), which are interconnected via bridging SEt(2) ligands. However, we could not reproduce the preparation of a coordination polymer with composition [(Et(2)S)(3){Cu(4)(mu(3)-Br)(4)}](n) as reported in Inorg. Chem. 1975, 14, 1667. In contrast, the autoassembly reaction of SEt(2) with CuBr results in the formation of a novel 1D coordination…

(S,S,S,S)-Nebivolol hydro-chloride hemihydrate.

The asymmetric unit of the title hydrated salt, C22H26F2NO4+·Cl−·0.5H2O, consists of an (S,S,S,S)-nebivolol {nebivol = bis[2-(6-fluoro-3,4-dihydro-2H-1-benzopyran-2-yl)-2-hydroxyethyl]ammonium} cation, a chloride anion and a half-occupancy water molecule. The dihedral angle between the mean planes of the benzene rings is 50.34 (12)°. The pyran rings adopt half-chair conformations. The crystal packing features O—H...O hydrogen bonds and weak N—H...Cl, O—H...Cl, and O—H...Cl interactions, producing layers along (010).

Boron functionalization of BODIPY by various alcohols and phenols.

The synthesis of new B–O BODIPY derivatives functionalized with different alkoxy or diarylalkoxy derivatives is described. These compounds were synthesized from the reaction of different B–F BODIPY precursors with various alcohols and phenols, in the presence of AlCl3. Water-soluble dyes could be synthesized as well with this method, specifically by the introduction of polyethyleneglycol (PEG) groups. A photophysical study of the different compounds was performed, and showed that the B–O BODIPY derivatives exhibit rich fluorescence properties. Finally, the conjugation of the BODIPY core has been extended using two distyryl groups, hence providing NIR emitting BODIPY derivatives, in which on…

Exploring the redox reactivity of magnesium porphine. Insight into the origins of electropolymerisation.

International audience; Magnesium(II) porphine, MgP (1), was synthesised according to the Lindsey procedure allowing to isolate and crystallise 1-formyldipyrromethane (2) as a synthetic intermediate. Unprecedented Xray diffraction studies revealed multiple intermolecular associations in the crystal between neighbouring units of 2, namely hydrogen bond and CH … π. The electrochemical behaviour of 1 was examined by means of cyclic voltammetry. In oxydation, two well-defined and distinct steps are assigned to macrocycle concerned electron transfers yielding initially the π-cation radical and π dication, respectively. The highly reactive dication condenses neutral magnesium porphine to form a d…

Crystal structure of (R)-6-fluoro-2-[(S)-oxiran-2-yl]chroman

The title compound, C11H11FO2, is a building block in the synthesis of the active pharmaceutical ingredient DL-nebivolol. The synthesis starting from the enantiomerically pure (R)-6-fluoro-4-oxo-3,4-dihydro-2H-chromene-2-carboxylic acid resulted in a mixture of two stereoisomers, namely (R)-6-fluoro-2-[(S)-oxiran-2-yl]chroman and (R)-6-fluoro-2-[(R)-oxiran-2-yl]chroman. The mixture was separated by column chromatography but only one stereoisomer crystallized. The X-ray structure analysis revealed that the solid consisted of theR,Sisomer. A similar procedure was repeated for (S)-6-fluoro-4-oxo-3,4-dihydro-2H-chromene-2-carboxylic acid and, in this case, theS,Risomer was produced as a crystal…

Two-Photon Absorption Properties and Structures of BODIPY and Its Dyad, Triad and Tetrad.

A series consisting of a dyad, a triad and a tetrad containing either two, three and four BODIPY units, respectively, has been synthesized and fully characterized and compared to two mono-BODIPY analogs (used as references). The one- and two-photon photophysical properties have been measured and the X-ray structures of four of the BODIPY derivatives have been determined. In the 700-900 nm range, the two-photon absorption (TPA) cross sections range from 30 GM to 160 GM for these compounds.

Efficient Synthesis of Multifunctional Chelating Agents Based on Tetraazacycloalkanes

An efficient route has been developed for the synthesis of multifunctional tetraazacycloalkanes (in particular 1,4,7,10-tetraazacyclotridecane) incorporating an aminomethyl pendant arm on the carbon skeleton. Starting from the appropriate C-functionalized bisaminal-protected intermediate, the target macrocycles were easily obtained by means of a step-by-step introduction of the desired functional groups onto the free primary amine group, followed by deprotection of the bisaminal intermediates. This straightforward and versatile synthetic approach paves the way for the design of a new family of multifunctional chelators.

Effect of t-BuS vs. n-BuS on the topology, Cu⋯Cu distances and luminescence properties of 2D Cu4I4/RS(CH2)4SR metal–organic frameworks

CuI reacts with RS(CH2)4SR (R = n-Bu (L1); t-Bu (L2)) to afford the 2D coordination polymers [Cu4I4{μ-RS(CH2)4SR}2]n (R = n-Bu (1); t-Bu (2)). Their grid networks exhibit nodal Cu4(μ3-I)4 clusters interconnected by dithioethers with mean Cu⋯Cu distances of 2.7265(10) and 2.911(2) A for 1 and 2, respectively. This difference translates in a blue shift of the solid state emission bands and a decrease in emission lifetimes when trading R = n-Bu to the bulky t-Bu.

A 4-tert-butylcalix[4]arene tetrahydroxamate podand based on the 1-oxypiperidine-2-one (1,2-PIPO−) chelate. Self-assembly into a supramolecular ionophore driven by coordination of tetravalent zirconium or hafnium(iv)

An octadentate tetrahydroxamic calix[4]arene podand incorporating 1-hydroxypiperidine-2-one (1,2-PIPOH) binding units has been designed as a specific chelator for tetravalent metal cations like Zr4+ or Hf4+. This receptor, which can be considered as the first ever abiotic ligand possessing only cyclic six-membered hydroxamate groups, has been synthesized and characterized in its tetraprotonated form (1H4). Contrary to expectation, however, this new chelator did not form a 1 : 1 complex upon reaction with M(acac)4 (M = Zr and Hf; acac = acetylacetonate), but rather self-assembled into a dimeric species of 2 : 2 stoichiometry. The latter could be characterized in solution by mass spectrometry…

Bis(4-methylthio)phenylthiomethane as assembling ligand for the construction of Cu(I) and Hg(II) coordination polymers. Crystal structures and topological (AIM) analysis of the bonding

International audience; The novel 1D coordination polymer (CP) [{Cu(mu(2)-Br)(2)Cu}(mu-L2)(2)] CP2 has been obtained by reaction of the tetrakisthioether p-MeSC6H4SCH2SC6H4SMe-p (L2) with CuBr in a 1: 2 metal-to ligand ratio. In contrast to the previously described CP [{Cu(mu(2)-Br)(2)Cu}(mu-L1)(2)] CP1 obtained by reaction of the tetrakisthioether p-MeOC6H4SCH2SC6H4OMe-p (L1) with CuBr, the two independent extended 1D ribbons contain bent Cu(mu(2)-Br)(2)Cu units of the butterfly-type with short Cu center dot center dot center dot Cu separations of 2.679(1) and 2.613(1) angstrom. In contrast to the common planar rhomboid Cu(mu(2)-Br)(2)Cu cluster, this butterfly-shaped geometry of the core …

Modular P-Chirogenic Phosphine-Sulfide Ligands: Clear Evidence for Both Electronic Effect and P-Chirality Driving Enantioselectivity in Palladium-Catalyzed Allylations

Using the ephedrine methodology, modular stereoselective syntheses of a new class of P-chirogenic phosphines bearing a sulfur-chelating arm (P*,S-hybrid ligand) are described. A first series of syntheses based on a Fries-like rearrangement of P-chirogenic phosphinite-boranes, which are prepared from 2-bromobenzyl or 2-bromophenethyl alcohol and are mediated by metal–halide exchange, have been performed. This rearrangement affords phosphine-boranes stereospecifically with an o-hydroxyalkylphenyl substituent. The latter residue is subsequently converted into a sulfur-containing group. In a second series, the stereoselective syntheses were achieved according to a new strategy involving a react…

Copper(I) Halides (X = Br, I) Coordinated to Bis(arylthio)methane Ligands: Aryl Substitution and Halide Effects on the Dimensionality, Cluster Size and Luminescence Properties of the Coordination Polymers

Bis(phenylthio)methane (L1) reacts with CuI to yield the 1D-coordination polymer [{Cu4(μ3-I)4}(μ-L1)2]n (1) bearing cubane Cu4I4 clusters as connecting nodes. The crystal structures at 115, 155, 195, and 235 K provided evidence for a phase transition changing from the monoclinic space group C2/c to P21/c. The self-assembly process of CuI with bis(p-tolylthio)methane (L2), bis(4-methoxyphenylthio)methane (L3), and bis(4-bromo-phenylthio)methane (L4) affords the 1D-coordination polymers [{Cu4(μ3-I)4}(μ-Lx)2]n (x = 2, 3, or 4). Compounds 2 and 4 are isostructural with C2/c low temperature polymorph of 1, whereas the inversion centers and 2-fold axes are lost in 3 (space group Cc). The use of b…

Design and photophysical properties of zinc(II) porphyrin-containing dendrons linked to a central artificial special pair.

The click chemistry synthesis and photophysical properties, notably photo-induced energy and electron transfers between the central core and the peripheral chromophores of a series of artificial special pair-dendron systems (dendron = G1, G2, G3; Gx = zinc(II) tetra-meso-arylporphyrin-containing polyimides) built upon a central core of dimethylxanthenebis(metal(II) porphyrin) (metal = zinc, copper), are reported. The dendrons act as singlet and triplet energy acceptors or donors, depending on the dendrimeric systems. The presence of the paramagnetic d(9) copper(II) in the dendrimers promotes singlet-triplet energy transfer from the zinc(II) tetra-meso-arylporphyrin to the bis(copper(II) por…

Synthesis, Characterization, and Electrochemistry of Open-Chain Pentapyrroles and Sapphyrins with Highly Electron-Withdrawing meso -Tetraaryl Substituents

International audience; A series of open-chain pentapyrroles and sapphyrins with highly electron-withdrawing substituents (i.e., CN, CF3 , or CO2 Me) on the meso-phenyl rings was synthesized and characterized as to the spectral properties, protonation reactions, and electrochemistry in non-aqueous media. The investigated compounds are represented as (Ar)4 PPyH3 and (Ar)4 SapH3 where PPy and Sap correspond to the tri-anion of the open-chain pentapyrrole and sapphyrin, respectively, and Ar=p-CNPh, p-CF3 Ph, or p-CO2 MePh. UV/Vis and 1 H NMR spectroscopy as well as mass spectrometry data are given for the confirmation of the structures for the newly synthesized compounds. An X-ray structure fo…

Cobalt Corroles with Bis‐Ammonia or Mono‐DMSO Axial Ligands. Electrochemical, Spectroscopic Characterizations and Ligand Binding Properties

International audience; Four bis-ammonia ligated cobalt corroles and four mono-DMSO ligated cobalt corroles with different mesoaryl substituents on the macrocycle (A 2 Band A 3-corroles) were synthesized and investigated as to their electrochemical and spec-troscopic properties under different solution conditions. The complexation energies of the investigated cobalt corroles were theoretically calculated to illustrate the propensity of the cobalt center for pentacoordination or hexa-coordination with various axial ligands (DMSO, CO, py and NH 3). The structure of one hexacoordinate bis-NH 3 cobalt corrole complex was also determined by X-ray diffraction.

A bacteriochlorin-diketopyrrolopyrrole triad as a donor for solution-processed bulk heterojunction organic solar cells

We have designed an A–π–D–π–A small-molecule triad consisting of a bacteriochlorin (BC) donor central core linked with two diketopyrrolopyrrole (DPP) acceptors via ethynyl bridges (BC-DPP-1). BC-DPP-1 has a narrow optical bandgap of 1.38 eV with highest occupied molecular orbital and lowest unoccupied molecular orbital energy levels of −4.93 eV and −3.40 eV, respectively, and it was used as an electron donor along with [6,6]-phenyl-C71-butyric acid methyl ester (PC71BM) as an acceptor for solution-processed small-molecule organic solar cells. After optimizing the weight ratio between BC-DPP-1 and PC71BM and pyridine as a solvent additive and subsequent solvent vapor annealing using THF, an …

Luminescent P-Chirogenic Copper Clusters

P-chirogenic clusters of the cubanes [Cu4I4L4] (L = chiral phosphine) were prepared from (+)- and (-)-ephedrine with L = (S)- or (R)-(R)(Ph)(i-Pr)P (with R = CH3 (seven steps) or C17H35 (10 steps)) with e.e. up to 96%. The X-ray structure of [Cu4I4((R)-(CH3)(Ph)(i-Pr)P)4] confirmed the cubane structure with average Cu···Cu and Cu···I distances of 2.954 and 2.696 Å, respectively. The cubane structure of the corresponding [Cu4I4((S)-(CH3)(Ph)(i-Pr)P)4] was established by the comparison of the X-ray powder diffraction patterns, and the opposite optical activity of the (S)- and (R)-ligand-containing clusters was confirmed by circular dichroism spectroscopy. Small-angle X-ray scattering patterns…

Synthesis, electrochemistry, protonation and X-ray analysis of meso-aryl substituted open-chain pentapyrroles

Five meso-tetraaryl open-chain pentapyrroles were synthesized and characterized as to their electrochemistry and protonation reactions in nonaqueous media. The investigated compounds are represented as (Ar)4PPyH3 where Ar [Formula: see text],[Formula: see text]-F2Ph, [Formula: see text]-BrPh, Ph, [Formula: see text],[Formula: see text],[Formula: see text]-(OMe)3Ph or [Formula: see text]-MePh and were characterized by UV-vis and 1H NMR spectroscopy, mass spectrometry and electrochemistry. Cyclic voltammetry was used to measure redox potentials, while protonation involving the conversion of (Ar)4PPyH3 to [(Ar)4PPyH5][Formula: see text] was monitored by UV-vis absorption spectroscopy. Equilib…

Diamondoid Nanostructures as sp 3 ‐Carbon‐Based Gas Sensors

Diamondoids, sp3 -hybridized nanometer-sized diamond-like hydrocarbons (nanodiamonds), difunctionalized with hydroxy and primary phosphine oxide groups, enable the assembly of the first sp3 -C-based chemical sensors by vapor deposition. Both pristine nanodiamonds and palladium nanolayered composites can be used to detect toxic NO2 and NH3 gases. This carbon-based gas sensor technology allows reversible NO2 detection down to 50 ppb and NH3 detection at 25-100 ppm concentration with fast response and recovery processes at 100 °C. Reversible gas adsorption and detection is compatible with 50 % humidity conditions. Semiconducting p-type sensing properties are achieved from devices based on prim…

Synthesis, UV/vis, FT-IR and Mössbauer spectroscopic characterization and molecular structure of the Bis[4-(2-aminoethyl)morpholine](tetrakis(4-metoxyphenyl)porphyrinato) iron(II) complex

International audience; The synthesis, the UV-visible, FT-IR and Mossbauer spectroscopy and the crystal structure characterizations of the bis[4-(2-Aminoethyl)morpholine]tetrakis(4-metoxyphenyl)porphy-rinato)iron(II) complex are described. The title compound crystallizes in the triclinic, space group P-1, with a = 11.1253(4) angstrom, b = 11.2379(4) angstrom, c = 11.5488(4) angstrom, alpha = 72.304(2)degrees, beta = 86.002(2)degrees gamma = 72.066(2)degrees, V = 1308.28(8) angstrom(3), Z = 1. The Mossbauer data are consistent with an iron(II) low-spin (S = 0) porphyin species. The spin-state is confirmed by the value of the average equatorial iron-nitrogen pyrrole distance (Fe-Np = 1.988(2)…

Synthesis of Isoxazole and 1,2,3-Triazole Isoindole Derivatives via Silver- and Copper-Catalyzed 1,3-Dipolar Cycloaddition Reaction.

International audience; The CuI-or Ag 2 CO 3-catalyzed [3+2] cycloaddition of propargyl-substituted dihydroisoindolin-1-one (3) with arylnitrile oxides 1a-d (Ar = Ph, p-MeC 6 H 4 , p-MeOC 6 H 4 , p-ClC 6 H 4) produces in good yields novel 3,5-disubstituted isoxazoles 4 of the ethyl-2-benzyl-3-oxo-1-((3-arylisoxazol-5yl)methyl)-2,3-dihydro-1H-isoindole-1-carboxylate type. With aryl azides 2a-d (Ar = Ph, p-MeC 6 H 4 , p-OMeC 6 H 4 , p-ClC 6 H 4), a series of 1,4-disubstituted 1,2,3-triazoles 6 (ethyl-2-benzyl-3-oxo-1-((1-aryl-1H-1,2,3-triazol-4-yl)methyl)-2,3-dihydro-1H-isoindole-1-carboxylates) was obtained. The reactions proceed in a regioselective manner affording exclusively racemic adduc…

Remarkable Inertness of Copper(II) Chelates of Cyclen-Based Macrobicycles with Two trans-N-Acetate Arms

Two cross-bridged cyclen-based macrocycles with two trans-N-acetic acid arms, one having a dibenzofuran (DBF) moiety as the bridge, H2L1, and the other a diphenyl ether (DPE) one, H2L2, were synthesized. Both compounds behave as "proton sponges." The thermodynamic stability constants for the Cu(2+), Zn(2+), Al(3+), and Ga(3+) complexes of both compounds were determined. They exhibit an excellent thermodynamic selectivity for copper(II), ensuring that metal ions largely present in the human body do not interfere with the copper(II) chelates. All complexes are very slow to form, and [CuL2] and [CuL1] are extremely inert to demetallate, especially [CuL2]. The acid-assisted dissociation of [CuL…

Synthesis, spectroscopic, cyclic voltammetry properties and molecular structure of the thiocyanato-N meso-tetratolylporphyrinato zinc(II) ion complex

International audience; This paper describes the synthesis of the (thiocyanato-N)(meso-tetratolylporphyrinato)zinc(II) chlorobenzene monosolvate complex with the formula [K(2,2,2-crypt)][Zn(TTP)(NCS)]·C6H5Cl (I) using the cryptand-222 to solubilize potassium thiocyanate in chlorobenzene solvent. Complex (I) has been characterized by elementary analysis, IR, UV–vis, 1H NMR and MS, and the structure of this new zinc(II) metalloporphyrin been examined crystallographically. A cyclic voltammetry investigation was also carried out on this species. The title compound crystallizes in the triclinic, space group P-1, with a = 11.5151(7) Å, b = 15.212(10) Å, c = 20.1093(12) Å, α = 80.428(4)°, β = 74.9…

New insights on the electronic, magnetic, electric and molecular structure of a bis-(4-cyanopyridine) iron(III) complex with the meso-tetrakis(4-methoxyphenyl)porphyrin

International audience; We have successfully synthesized and characterized a new low-spin iron(III) bis(4-cyanopyridine) complex with a meso-porphyrin substituted in the para positions of the phenyls by the methoxy group, namely the bis(4-cyanopyridine)[(meso-tetrakis(4-metoxyphenylporphyrinato)]iron(III) trifluoromethanesulfonate chlorobenzene monosolvate complex with the formula [FeIII(TMPP)(4-CNpy)2]SO3CF3.C6H5Cl (I). This species was characterized through ultraviolet–visible, Fourier-transform infrared and Mössbauer spectroscopy as well as by SQUID magnetometry, cyclic voltammetry, and X-ray crystallography. These characterizations indicated that our synthetic heme model is a low-spin (…

Synthesis, crystallographic and electrochemical study of ethynyl[2.2]paracyclophane derived cobalt metallatetrahedranes

Abstract A series of alkynyl cobalt complexes [Co2(μ-η2-HCC–PCP)(CO)6−nLn] [n = 0 (2); n = 2, L2 = dppa (3), dppm (4), dcpm (6), 2 P(OPh)3 (7)] and [Co2(CO)4L2]2(μ-η2:μ-η2-HCC–PCP–CCH)] (L2 = dppm (8), dcpm (9); (PCP = [2.2]paracyclophane) has been prepared and characterized. The molecular structures of 3 and 4, as well as that of [Co2(CO)4(μ-CO)2(μ2-dcpm)] (5), have been determined by X-ray diffraction. Electrochemical studies (Cyclic Voltammetry, Rotating Disk Electrode) and luminescence spectroscopy have been used to evaluate the extent of the electronic communication through the PCP motif using the “Co2C2” centres as a probe. No electronic coupling between the Co2(CO)n centres via the b…

Regio- and Stereoselective Synthesis of Spiropyrrolizidines and Piperazines through Azomethine Ylide Cycloaddition Reaction.

A series of original spiropyrrolizidine derivatives has been prepared by a one-pot three-component [3 + 2] cycloaddition reaction of (E)-3-arylidene-1-phenyl-pyrrolidine-2,5-diones, l-proline, and the cyclic ketones 1H-indole-2,3-dione (isatin), indenoquinoxaline-11-one and acenaphthenequinone. We disclose an unprecedented isomerization of some spiroadducts leading to a new family of spirooxindolepyrrolizidines. Furthermore, these cycloadducts underwent retro-1,3-dipolar cycloaddition yielding unexpected regioisomers. Upon treatment of the dipolarophiles with in situ generated azomethine ylides from l-proline or acenaphthenequinone, formation of spiroadducts and unusual polycyclic fused pip…

Enantioselective Hydrogenation Catalysis Aided by a σ-Bonded Calix[4]arene to a P-Chirogenic Aminophosphane Phosphinite Rhodium Complex

The first P-chirogenic aminophosphane−phosphinite (AMP*P) ligand (4a) supported on the upper rim of a calix[4]arene moiety was synthesized in two steps using the ephedrine methodology. Ligand 4a wa...

Effects of preorganization in the chelation of UO22+ by hydroxamate ligands: cyclic PIPO– vs linear NMA–

International audience; Many siderophores incorporate as bidentate chelating subunits linear and more seldomly cyclic hydroxamate groups. In this work, a comparative study of the uranyl binding properties in aqueous solution of two monohydroxamic acids, the prototypical linear N-methylacetohydroxamic acid (NMAH) and the cyclic analog 1-hydroxypiperidine-2-one (PIPOH), has been carried out. The complex [UO2(PIPO)(2)(H2O)] crystallized from slightly acidic water solutions (pH < 5), and its molecular structure was determined by X-ray diffraction. The uranyl speciation in the presence of both ligands has been thoroughly investigated in a 0.1 M KNO3 medium at 298.2 K by the combined use of four …

Series of charge transfer complexes obtained as crystals in a confined environment

A series of charge transfer complexes (CTCs) were successfully formed by solvent free processing techniques, using the 1,2,4,5-tetracyano benzene (TCNB) as πA molecule and a series of p-dihydroquinones (H2Qs) as πD counterparts. Additionally to the classical co-evaporation techniques, we obtained CTCs in less than an hour, in a very simple confined environment, between two 100 μm – spaced glass plates. A systematical study by Raman spectroscopy on crystals highlighted the CTCs formation. Moreover, three new crystalline structures were obtained, namely TCNB-H2Q that crystallizes in columns connected to each other by H-bonds, while with the methoxy- and dimethoxy-H2Qs the CTC forms crystals w…

Selective CO2 adsorption by a triazacyclononane-bridged microporous metal-organic framework.

Metal-organic frameworks constructed by self-assembly of metal ions and organic linkers have recently been of great interest in the preparation of porous hybrid materials with a wide variety of functions. Despite much research in this area and the large choice of building blocks used to fine-tune pore size and structure, it remains a challenge to synthesise frameworks composed of polyamines to tailor the porosity and adsorption properties for CO(2). Herein, we describe a rigid and microporous three-dimensional metal-organic framework with the formula [Zn(2)(L)(H(2)O)]Cl (L=1,4,7-tris(4-carboxybenzyl)-1,4,7-triazacyclononane) synthesised in a one-pot solvothermal reaction between zinc ions a…

ChemInform Abstract: Thioetherification of Chloroheteroarenes: A Binuclear Catalyst Promotes Wide Scope and High Functional-Group Tolerance.

The nucleophilic substitution of a variety of chloro- and bromohetarenes with arylthiols is optimized to use [PdCl(allyl)]2 in combination with a ferrocenyltetraphosphane as ligand.

ChemInform Abstract: Boron Functionalization of BODIPY by Various Alcohols and Phenols

The synthesis of new B–O BODIPY derivatives functionalized with different alkoxy or diarylalkoxy derivatives is described. These compounds were synthesized from the reaction of different B–F BODIPY precursors with various alcohols and phenols, in the presence of AlCl3. Water-soluble dyes could be synthesized as well with this method, specifically by the introduction of polyethyleneglycol (PEG) groups. A photophysical study of the different compounds was performed, and showed that the B–O BODIPY derivatives exhibit rich fluorescence properties. Finally, the conjugation of the BODIPY core has been extended using two distyryl groups, hence providing NIR emitting BODIPY derivatives, in which on…

1,8-Bis[3-(triethoxysilyl)propyl]-1,8-diazoniatricyclo[9.3.1.14,8]hexadecane diiodide

The organic molecule of title compound, C30H66N4O6Si22+&amp;#183;2I&amp;#8722;, is located around a centre of symmetry. The structure exhibits disorder of the triethoxy groups with the ratios 0.78&amp;#8197;(1)/0.22&amp;#8197;(1), 0.67&amp;#8197;(1)/0.33&amp;#8197;(1) and 0.58&amp;#8197;(1)/0.42&amp;#8197;(1).

Crystal structure of diaqua[5,10,15,20-tetrakis(4-methoxyphenyl)porphyrinato-κ4N]iron(III) diaqua(18-crown-6)potassium bis(trifluoromethanesulfonate)–18-crown-6 (1/2)

In the title compound, [FeIII(C48H36N4O2)(H2O)2][K(C12H24O6)(H2O)2](SO3CF3)2·2C12H24O6, the FeIIIatom is situated on an inversion centre and is octahedrally coordinated by four pyrrole N atoms of the deprotenated 5,10,15,20-tetrakis(4-methoxyphenyl)porphyrinate ligand and two water molecules. The average equatorial Fe—N(pyrrole) bond length [2.043 (6) Å] is consistent with a high-spin (S= 5/2) iron(III) metalloporphyrin derivative. The K+cation, which also lies on an inversion centre, is chelated by the six O atoms of one 18-crown-6 molecule and is additionally coordinated by two water molecules in a distorted hexagonal–bipyramidal geometry. In the crystal, the cations, anions and one non-c…

P-Chirogenic Phosphines Supported by Calix[4]arene: New Insight into Palladium-Catalyzed Asymmetric Allylic Substitution

The first P-chirogenic mono- and diphosphine ligands supported on the upper rim of a calix[4]arene moiety were synthesized using the ephedrine methodology. The lithiated calix[4]arene mono- and dianions both react with the oxazaphospholidine–borane, prepared from ephedrine, to afford regio- and stereoselectively the corresponding calix[4]arenyl aminophosphine–boranes, by cleavage of the heterocyclic ring at the P–O bond position. Subsequent reactions with HCl and then organolithium reagent and finally decomplexation with DABCO lead to the corresponding calix[4]arenyl mono- or diphosphines. Both enantiomers of the calix[4]arenyl phosphines were obtained either by using (+)- or (−)-ephedrine …

Selectively Functionalized Constrained Polyazamacrocycles: Building Blocks for Multifunctional Chelating Agents

A new class of cross-bridged and side-bridged 1,4,7,10-tetraazacyclotridecanes (homocyclens) bearing an aminomethyl pendant arm on the carbon skeleton has been prepared. The regioselectivity of the quaternization of the bis-aminal intermediates is discussed on the basis of X-ray diffraction and NMR experiments. These new polyazamacrocycles are valuable precursors of bifunctional chelating agents for applications in nuclear medicine.

Identifying three-way DNA junction-specific small-molecules

Three-way junction DNA (TWJ-DNA, also known as 3WJ-DNA) is an alternative secondary DNA structure comprised of three duplex-DNAs that converge towards a single point, termed the branch point. This point is characterized by unique geometrical properties that make its specific targeting by synthetic small-molecules possible. Such a targeting has already been demonstrated in the solid state but not thoroughly biophysically investigated in solution. Herein, a set of simple biophysical assays has been developed to identify TWJ-specific small-molecule ligands; these assays, inspired by the considerable body of work that has been reported to characterize the interactions between small-molecules an…

A triclinic polymorph of (−)-(S)-N-benzyl-2-[(R)-6-fluorochroman-2-yl]-2-hydroxyethanaminium bromide

The title salt, C18H21FNO2+·Br−, determined at 115 K, crystallizes in the triclinic space groupP1. The previously reported polymorph occurs in the monoclinic space groupP21and has two independent molecules in the asymmetric unit [Peeterset al.(1993).Acta Cryst.C49, 2157–2160]. In the title molecule, the pyran rings adopt half-chair conformations. The absolute configuration isSfor the hydroxy-bearing C atom andRfor the asymmetric C atom in the dihydropyran unit. In the crystal, the components are linked by N—H...Br and O—H...Br hydrogen bonds, forming chains along thec-axis direction. The crystal studied was refined as an inversion twin.

(R)-(−)-Quinuclidin-3-ol

The structure of the title compound [alternatively called (R)-(−)-1-azabicyclo[2.2.2]octan-3-ol], C7H13NO, at 100 K has hexagonal (P61) symmetry. The structure shows a twist along the C—N pseudo-threefold axis. In the crystal, molecules are linkedviaO—H...N hydrogen bonds, forming infinite chains along thec-axis direction. The crystal studied was twinned by merohedry (twin law: 010, 100, 00-1; population: 0.925:0.075)

Efficient Synthesis of (P-Chirogenic) o-Boronated Phosphines from sec-Phosphine Boranes

An efficient synthesis of boronated phosphines with an o-phenylene-bridge prepared from sec-phosphine boranes and using benzyne chemistry is reported. Successive reactions of sec-phosphine boranes with n-BuLi and 1,2-dibromobenzene, and then with boron reagents, afford the o-boronatophenylphosphine derivatives in 71% yields. The use of P-chirogenic sec-phosphine boranes leads to the free boronated phosphines with retention of configuration at the P-center after decomplexation. The reaction of P-chirogenic o-boronatophenylphosphine with KHF2 affords the corresponding trifluoroborated phosphine with ee >98%.

Electrochemistry of Bis(pyridine)cobalt (Nitrophenyl)corroles in Nonaqueous Media

International audience; A series of bis(pyridine)cobalt corroles with one or three nitrophenyl groups on the meso positions of the corrole macrocycle were synthesized and characterized as to their electrochemical and spectroscopic properties in dichloromethane, benzonitrile, and pyridine. The potentials for each electrode reaction were measured by cyclic voltammetry and the electron-transfer mechanisms evaluated by analysis of the electrochemical data combined with UV-visible spectra of the neutral, electroreduced, and electroxidized forms of the corroles. The proposed electronic configurations of the initial compounds and the prevailing redox reactions involving the electroactive central c…

Conformational and structural studies of N-methylacetohydroxamic acid and of its mono- and bis-chelated uranium(VI) complexes

The thermodynamics and kinetics of the cis/trans isomerism of N-methylacetohydroxamic acid (NMAH) and its conjugated base (NMA(-)) have been reinvestigated in aqueous media by (1)H NMR spectroscopy. Hindered rotation around the central C-N bond due to electronic delocalization becomes slow enough on the NMR time scale to observe both rotamers in equilibrium in D2O at room temperature. By properly assigning the methyl group resonances, evidence for the prevalence of the E over the Z form is unambiguously provided [K300=[E]/[Z]=2.86(2) and 9.63(5) for NMAH and NMA(-), respectively], closing thereby a long-lasting dispute about the most stable conformer. To that end, calculations of the chemic…

Efficient Synthesis of 1,4,7-Triazacyclononane and 1,4,7-Triazacyclononane-Based Bifunctional Chelators for Bioconjugation (Eur. J. Org. Chem. 35/2014)

1,3-Dipolar cycloaddition of diaryldiazomethanes across N-ethoxy-carbonyl-N-(2,2,2-trichloroethylidene)amine and reactivity of the resulting 2-azabutadienes towards thiolates and cyclic amides

Abstract 1,3-dipolar cycloaddition of diaryldiazomethanes Ar2C N2 across Cl3C–CH N–CO2Et 1 yields Δ3-1,2,4-triazolines 2. Thermolysis of 2 leads, via transient azomethine ylides 3, to diaryldichloroazabutadienes [Ar(Ar')C N–CH CCl2] 4. Treatment of 4a (Ar = Ar' = C6H5) and 4c (Ar = Ar' = p-ClC6H4) with NaSR in DMF yields 2-azabutadienes [Ar2C N–C(H) C(SR)2] 5. In contrast, nucleophilic attack of NaStBu on 4 affords azadienic dithioethers [Ar2C N–C(StBu) C(H)(StBu)] (7a Ar = C6H5; 7b Ar' = p-ClC6H4). The reaction of 4a with NaSEt conducted in neat EtSH produces [Ph2C N–C(H)(SEt)–CCl2H] 8, which after dehydrochloration by NaOMe and subsequent addition of NaSEt is converted to [Ph2C N–C(SEt) C…

Efficient synthesis of new C-functionalized macrocyclic polyamines

A powerful synthetic route for the preparation of new poly-azamacrocycles, valuable precursors of bifunctional chelating agents with applications in nuclear medicine, is reported. The desired functional group was introduced onto the macro-cycle backbone during the cyclization step, thus avoiding the tedious preparation of a C-functionalized synthon. The regioselective reaction of macrocycles bearing an aminomethyl pendant arm with aldehydes is also described.

First bodipy–DOTA derivatives as probes for bimodal imaging

The synthesis and the photophysical studies of the first bodipy-DOTA and its In(III), Ga(III) and Cu(II) complexes are reported. The introduction of an isothiocyanate handle generates a new bimodal imaging agent capable of both optical and nuclear imaging.

Synthesis and Structural Study of Tetravalent (Zr 4+ , Hf 4+ , Ce 4+ , Th 4+ , U 4+ ) Metal Complexes with Cyclic Hydroxamic Acids

Six- and seven-membered cyclic hydroxamic acids, such as 1-hydroxypiperidine-2-one (1H, 1,2-PIPOH) and 1-hydroxyazepan-2-one (2H), have recently been identified in some mixed siderophores as one of their three chelating subunits. Compared to their ubiquitous noncyclic counterparts, cyclic hydroxamates are preorganized for metal binding. Surprisingly, the coordination chemistry of these bidentate, monoanionic ligands remains virtually unknown, even in the case of iron(III). We report herein the first structural study of the complexes of 1– and of 6–, an unsaturated seven-membered ring analog of 2–, with tetravalent cations of transition metals (zirconium and hafnium), lanthanide (cerium), an…

Water-Soluble Aza-BODIPYs: Biocompatible Organic Dyes for High Contrast In Vivo NIR-II Imaging

International audience; A simple NIR-II emitting water-soluble system has been developed and applied in vitro and in vivo. In vitro, the fluorophore quickly accumulated in 2D and 3D cell cultures and rapidly reached the tumor in rodents, showing high NIR-II contrast for up to 1 week. This very efficient probe possesses all the qualities necessary for translation to the clinic as well as for the development of NIR-II emitting materials.

Micelles as containers for self-assembled nanodevices: a fluorescent sensor for lipophilicity

Potentiometric titrations, fluorescence versus pH titrations, dynamic light scattering and fluorescence polarization anisotropy studies demonstrate that inside the nanodimensioned Triton X-100 micelles, 1-pyrenecarboxylic acid, PCOO-, forms an apical complex with the Zn2+ cation encircled by a lipophilic cyclen ligand and hugely increasing its fluorescence. The ability of the Zn2+-cyclen-PCOO- complex plus its micellar container to act as a fluorescent sensor to evaluate the lipophilicity of molecular species is demonstrated on the fatty acid series CH 3(CH2)xCOOH (x=0-16). At pH 7.4 a decrease in fluorescence is observed on the addition of fatty acids that is directly related to their chai…

Design of a multifunctionalizable BODIPY platform for the facile elaboration of a large series of gold(i)-based optical theranostics.

A simple trifunctional BODIPY platform was designed. The high potential of this platform was validated via the elaboration of twelve optical theranostics. More specifically, we reported on the synthesis, the characterization, the photophysical properties, and the evaluation of the hydrophilicity properties of the different BODIPY derivatives, as well as a theoretical rationalization of the intriguing chemical behavior of some of them. The antiproliferative evaluation and confocal imaging of the different compounds in three human and murine cancer cell lines were performed and analysed, along with the measurement of gold(I) uptake in one cancer cell line via ICP-MS.

Stereoselective synthesis of o-bromo (or iodo)aryl P-chirogenic phosphines based on aryne chemistry.

The efficient synthesis of chiral or achiral tertiary phosphines bearing an o-bromo (or iodo)aryl substituent is described. The key step of this synthesis is based on the reaction of a secondary phosphine borane with the 1,2-dibromo (or diiodo)arene, owing to the formation in situ of an aryne species in the presence of n-butyllithium. When P-chirogenic secondary phosphine boranes were used, the corresponding o-halogeno-arylphosphine boranes were obtained without racemization in moderate to good yields and with ee up to 99%. The stereochemistry of the reaction, with complete retention of the configuration at the P atom, has been established by X-ray structures of P-chirogenic o-halogenopheny…

Designing P-Chirogenic 1,2-Diphosphinobenzenes at Both P-Centers Using P(III)-Phosphinites

International audience; A new enantiodivergent synthesis of P-chirogenic 1,2-diphosphinobenzenes (DP*B) bearing the chirality on one or both phosphorus centers is reported using aryne chemistry. The principle is based on successive reactions of 1,2-dibromobenzene with sec-phosphide boranes, then DABCO to remove the borane, and finally with chlorophosphines or P(III)-chirogenic phosphinites. The efficiency of this synthesis was demonstrated by the stereoselective preparation of (S,S)-1,2-bis(o-anisylphenylphosphino)benzene. A comparison of DIPAMP and homochiral DP*B ligands in asymmetric Rh- or Pd-catalyzed reactions was reported.

Reactivity of CuI and CuBr toward Dialkyl Sulfides RSR: From Discrete Molecular Cu I S and Cu I S Clusters to Luminescent Copper(I) Coordination Polymers

The 1D coordination polymer (CP) [(Me2S)3{Cu2(μ-I)2}]n (1) is formed when CuI reacts with SMe2 in n-heptane, whereas in acetonitrile (MeCN), the reaction forms exclusively the 2D CP [(Me2S)3{Cu4(μ-I)4}]n (2) containing “flower-basket” Cu4I4 units. The reaction product of CuI with MeSEt is also solvent-dependent, where the 1D polymer [(MeSEt)2{Cu4(μ3-I)2(μ2-I)2}(MeCN)2]n (3) containing “stepped-cubane” Cu4I4 units is isolated in MeCN. In contrast, the reaction in n-heptane affords the 1D CP [(MeSEt)3{Cu4(μ3-I)4}]n (4) containing “closed-cubane” Cu4I4 clusters. The reaction of MeSPr with CuI provides the structurally related 1D CP [(MeSPr)3{Cu4(μ3-I)4}]n (5), for which the X-ray structure has…

Supramolecular Architectures Based on Phosphonic Acid Diesters

The interest of phosphonic acid dialkyl esters for generation of metal-organic materials is discussed using derivatives of porphyrin and 1,10-phenanthroline series as representative examples.

Reinforced cyclam derivatives functionalized on the bridging unit

International audience; A new synthetic method has been developed for the preparation of reinforced cyclams (1,4,8,11-tetraazacyclotetradecane) C-functionalized on the bridging unit, by using a "one pot" reaction starting from the appropriate bis-aminal cyclam intermediate. The high reactivity of quaternized aminal moiety toward nucleophilic agent has been used to elaborate a new class of cross-bridged and side-bridged cyclam derivatives containing cyanide group on the ethylene bridge. Several chelators and corresponding copper(II) complexes have been prepared and characterized by X-ray diffraction. These new constrained polyazamacrocycles are valuable precursors of bifunctional chelating a…

ChemInform Abstract: Regio- and Stereoselective Synthesis of Spiropyrrolizidines and Piperazines Through Azomethine Ylide Cycloaddition Reaction.

A series of original spiropyrrolizidine derivatives has been prepared by a one-pot three-component [3 + 2] cycloaddition reaction of (E)-3-arylidene-1-phenyl-pyrrolidine-2,5-diones, l-proline, and the cyclic ketones 1H-indole-2,3-dione (isatin), indenoquinoxaline-11-one and acenaphthenequinone. We disclose an unprecedented isomerization of some spiroadducts leading to a new family of spirooxindolepyrrolizidines. Furthermore, these cycloadducts underwent retro-1,3-dipolar cycloaddition yielding unexpected regioisomers. Upon treatment of the dipolarophiles with in situ generated azomethine ylides from l-proline or acenaphthenequinone, formation of spiroadducts and unusual polycyclic fused pip…

The Cu(II) complex of a C-lipophilized 13aneN4 macrocycle with an additional protonable amino group as micellar anion receptor.

Three 13aneN4 macrocyclic ligands have been prepared bearing a -CH(2)NHR side arm (R = H, n-C(5)H(11), n-C(10)H(21)) on a carbon atom. When Cu(2+) is complexed in the macrocyclic ring, the amino group of the side arm undergoes an acid-base protonation equilibrium but it is not able to coordinate apically the metal cation even when it is deprotonated. The Cu(2+) complex with the ligand bearing the longest appended aliphatic chain is fully confined inside Triton X-100 micelles, and its ability to bind and sequestrate a series of anions inside micelles has been studied at two different pH values, i.e. both with protonated and neutral side-arm amino group. The favourable role played by the prot…

Ligand Noninnocence in Cobalt Dipyrrin–Bisphenols: Spectroscopic, Electrochemical, and Theoretical Insights Indicating an Emerging Analogy with Corroles

Three cobalt dipyrrin-bisphenol (DPPCo) complexes with different meso-aryl groups (pentafluorophenyl, phenyl, and mesityl) were synthesized and characterized based on their electrochemistry and spectroscopic properties in nonaqueous media. Each DPPCo undergoes multiple oxidations and reductions with the potentials, reversibility, and number of processes depending on the specific solution conditions, the specific macrocyclic substituents, and the type and number of axially coordinated ligands on the central cobalt ion. Theoretical calculations of the compounds with different coordination numbers are given in the current study in order to elucidate the cobalt-ion oxidation state and the innoc…

Efficient Synthesis of 1,4,7-Triazacyclononane and 1,4,7-Triazacyclononane-Based Bifunctional Chelators for Bioconjugation

The reaction of diethylenetriamine with chloroacetaldehyde yielded a bicyclic aminal intermediate for the synthesis of 1,4,7-triazacyclononane (TACN), a macrocyclic polyamine the derivatives of which find applications as catalysts, bleaching agents, and chelators for medical imaging. This new synthetic protocol outperforms the synthetic methods described so far because it does not involve any cyclization step. Moreover, this aminal intermediate allowed access to a new family of TACN derivatives functionalized on the carbon skeleton, for example, C-aminomethyl-TACN. This novel compound is a precursor of valuable bifunctional chelating agents for nuclear medicine, in particular, for the prepa…

A3- and A2B-fluorocorroles: synthesis, X-ray characterization and antiviral activity evaluation against human cytomegalovirus infection

Twenty-nine fluorinated corroles were prepared, spectroscopically characterized, and studied for their antiviral activity against human cytomegalovirus infection. Six corroles were also fully characterized by X-ray crystallography giving insights on their geometrical features. The halogenated corroles reported herein exhibit significantly improved antiviral activity over their non-halogenated counterparts and over nitro-corrole analogs previously reported. Full activity of thirteen A3-corroles is achieved with four fluorine atoms present on the meso-phenyl ring reaching a selectivity index above 300. The maximum activity is achieved for A2B-corroles with selectivity indexes above 400. We th…

Real-Time Observation of “Soft” Magic-Size Clusters during Hydrolysis of the Model Metallodrug Bismuth Disalicylate

International audience; Colloidal bismuth therapeutics have been used for hundreds of years, yet remain mysterious. Here we report an X-ray pair distribution function (PDF) study of the solvolysis of bismuth disalicylate, a model for the metallodrug bismuth subsalicylate (Pepto-Bismol). This reveals catalysis by traces of water, followed by multistep cluster growth. The ratio of the two major species, {Bi9O7} and {Bi38O44}, depends on exposure to air, time, and the solvent. The solution-phase cluster structures are of significantly higher symmetry in comparison to solid-state analogues, with reduced off-center Bi3+ displacements. This explains why such “magic-size” clusters can be both stab…

ChemInform Abstract: o-(Hydroxyalkyl)phenyl P-Chirogenic Phosphines as Functional Chiral Lewis Bases.

The stereoselective synthesis of P-chirogenic phosphines bearing an o-hydroxyalkyl chain is described.

Formation of an unprecedented (CuBr)5 cluster and a zeolite-type 2D-coordination polymer: a surprising halide effect

A unique pentanuclear cluster within a zeolite-type polymer ([Cu5(μ4-Br)(μ3-Br)2(μ2-Br)2](μ2-MeSPr)3)n (1; void space >81%) and a luminescent 1D ([Cu(μ3-I)]4(MeSPr)3)n polymer, 2, are formed when MeSPr reacts with CuBr and CuI.

Crystal structure of tricarbonyl(μ-diphenylphosphido-κ2P:P)(methyldiphenylsilyl-κSi)bis(triphenylphosphane-κP)iron(II)platinum(0)(Fe—Pt)

The title compound belongs to the large family of heterodinuclear phosphide-bridged complexes. The Fe—Pt bond is of 2.7738 (4) Å and there is an unprecedented arrangement of the silyl ligand in a trans-position with respect to the metal–metal vector in the family of phosphide-bridged iron–platinum heterobimetallics.

Synthesis of P-Chirogenic Diphosphinotriazoles and Their Use in Asymmetric Catalysis

International audience; The stereoselective synthesis of P-chirogenic diphosphinotriazoles using ephedrine methodology was described. The coordination behavior of these compounds as P,P-ligands has been demonstrated by the preparation as well as the spectroscopic and X-ray crystallographic analyses of a palladium complex. The efficiency of these new P-chirogenic diphosphines in the palladiumcatalyzed asymmetric allylic substitution reaction was also evaluated.

Diaqua[5,10,15,20-tetrakis(4-chlorophenyl)porphyrinato-κ4N]iron(III) trifluoromethanesulfonate–4-hydroxy-3-methoxybenzaldehyde–water (1/1/2)

In the title compound, [Fe(C44H24Cl4N4)(H2O)2](SO3CF3)·C8H8O3·2H2O, the FeIIIcation is chelated by the four N atoms of the deprotonated tetrakis(4-chlorotetraphenyl)porphyrin (TClPP) and further coordinated by two water molecules in a distorted octahedral geometry. In the crystal, the cations, anions, 4-hydroxy-3-methoxybenzaldehyde and water molecules of crystallization are linked by classical O—H...O hydrogen bonds and weak C—H...O and C—H...Cl hydrogen bonds into a three-dimensional supramolecular architecture. The crystal packing is further stabilized by weak C—H...π interactions involving pyrrole and benzene rings. π–π stacking between parallel benzene rings of adjacent 4-hydroxy-3-met…

Copper( ii ) complexes with phosphorylated 1,10-phenanthrolines: from molecules to infinite supramolecular arrays

International audience; The reaction of phosphorylated 1,10-phenanthrolines 3-Pphen, 3,8-Pphen and 4,7-Pphen (3-Pphen = 3-diethoxyphosphorylphenanthroline, 3,8-Pphen = 3,8-bis(diethoxyphosphoryl) phenanthroline, 4,7-Pphen = 4,7-bis(diethoxyphosphoryl) phenanthroline) and hydrated copper(II) nitrate in a 1 : 1 ratio leads to the formation of supramolecular architectures. In the 1D coordination polymer [Cu(3-Pphen)(NO3)(2)](n) (2) the copper atom is coordinated to only one phenanthroline ligand and the coordination sphere is completed by two oxygen atoms of nitrate anions and the oxygen atom of the phosphoryl group from the neighbouring phenanthroline ligand. Complex Cu(3,8-Pphen)(NO3)(2) (3)…

1,3-Dipolar Cycloaddition Reactions of Indan-1-one Enamines across Arylnitrile Oxides Leading to Novel Cyclic Isoxazoline Derivatives

Synthesis of a series of cyclic fused-isoxazolines has been accomplished by regioselective and diastereoselective 1,3-dipolar cycloaddition of 3-methylindan-1-one enamines (1a, 1b, 1c) and 3-phenylindan-1-one enamines (2a, 2b, 2c) to arylnitrile oxides (3d, 3e, 3f, 3g, 3h). The structure of the cycloadducts was elucidated by 1H and 13C NMR spectroscopy. The proposed regio- and stereochemistry of fused-compounds (4) and (5) has also been corroborated by two single-crystal X-ray diffraction studies carried out on 4-methyl-8b-morpholinyl-3-(p-tolyl)-4H-3a,8b-dihydroindeno[2,3-d]isoxazoline (4be) and 3-(p-anisyl)-4-phenyl-8b-pyrrolidinyl-4H-3a,8b-dihydroindeno[2,3-d]isoxazoline (5af) and by mea…

1,4-Bis(arylthio)but-2-enes as Assembling Ligands for (Cu2X2)n (X = I, Br; n = 1, 2) Coordination Polymers: Aryl Substitution, Olefin Configuration, and Halide Effects on the Dimensionality, Cluster Size, and Luminescence Properties

CuI reacts with E-PhS(CH2CH═CHCH2)SPh, L1, to afford the coordination polymer (CP) [Cu2I2{μ-E-PhS(CH2CH═CHCH2)SPh}2]n (1a). The unprecedented square-grid network of 1 is built upon alternating two-dimensional (2D) layers with an ABAB sequence and contains rhomboid Cu2(μ2-I)2 clusters as secondary building units (SBUs). Notably, layer A, interconnected by bridging L1 ligands, contains exclusively dinuclear units with short Cu···Cu separations [2.6485(7) A; 115 K]. In contrast, layer B exhibits Cu···Cu distances of 2.8133(8) A. The same network is observed when CuBr reacts with L1. In the 2D network of [Cu2Br2{μ-E-PhS(CH2CH═CHCH2)SPh}2]n (1b), isotype to 1a, one square-grid-type layer contain…

DOTAGA-anhydride: a valuable building block for the preparation of DOTA-like chelating agents.

International audience; A DOTA derivative that contains an anhydride group was readily synthesized by reacting DOTAGA with acetic anhydride and its reactivity was investigated. Opening the anhydride with propylamine led to the selective formation of one of two possible regioisomers. The structure of the obtained isomer was unambiguously determined by 1D and 2D NMR experiments, including COSY, HMBC, and NOESY techniques. This bifunctional chelating agent offers a convenient and attractive approach for labeling biomolecules and, more generally, for the synthesis of a large range of DOTA derivatives. The scope of the reaction was extended to prepare DOTA-like compounds that contained various f…

Thioetherification of Chloroheteroarenes: A Binuclear Catalyst Promotes Wide Scope and High Functional-Group Tolerance

A constrained binuclear palladium catalyst system affords selective thioetherification of a wide range of functionalized arenethiols with chloroheteroaromatic partners with the highest turnover numbers (TONs) reported to date and tolerates a large variety of reactive functions. The scope of this system includes the coupling of thiophenols with six- and five-membered 2-chloroheteroarenes (i.e., functionalized pyridine, pyrazine, quinoline, pyrimidine, furane, and thiazole) and 3-bromoheteroarenes (i.e., pyridine and furane). Electron-rich congested thiophenols and fluorinated thiophenols are also suitable partners. The coupling of unprotected amino-2-chloropyridines with thiophenol and the s…

Multiarm cyclam-grafted mesoporous silica: a strategy to improve the chemical stability of silica materials functionalized with amine ligands

We have explored in this work the stability and the reactivity of multiarm cyclam-grafted mesoporous silica samples in aqueous solution. A series of hybrid materials have been prepared by grafting silylated cyclam molecules bearing one, two, or four silyl groups onto both amorphous silica gel (K60) and ordered mesoporous silica (SBA15). Under these conditions, cyclam moieties are attached to the silica walls via one, two, or four arms. Various physicochemical techniques have been applied to characterize the functionalized solids (elemental analysis, 1H-29Si and 1H-13C CPMAS NMR, and N2 adsorption-desorption isotherms). The interest in two and four arms for improving the chemical stability i…

o-(Hydroxyalkyl)phenyl P-Chirogenic Phosphines as Functional Chiral Lewis Bases

The stereoselective synthesis of P-chirogenic phosphines bearing an o-hydroxyalkyl chelating arm is described. The synthesis is based either on the hydroxyalkylation of P-chirogenic o-bromophenylphosphines (borane) or on their carbonatation and then reduction. The hydroxyalkylation with benzaldehyde or pivalaldehyde affords a mixture of epimers which are isolated by chromatography and characterized by their X-ray structures. Preliminary assays of free P-chirogenic o-(hydroxyalkyl)phenyl phosphines, as new functional Lewis bases in catalyzed asymmetric aza-MBH reaction, lead to β-aminoester derivatives with ee values up to 74%.

Structural and Electrochemical Studies of Copper(I) Complexes with Diethoxyphosphoryl-1,10-phenanthrolines

Two series of copper(I) complexes with diethoxyphosphoryl-substituted 1,10-phenanthroline ligands were synthesized and characterized in the solid state and in solution. The first comprised mixed-ligand CuI complexes with phenanthroline and triphenylphosphine. The second series includes bis-chelates with two phenanthroline ligands. According to the X-ray data for the six complexes, the ditopic phenanthroline ligands exhibit bidentate coordination to the copper(I) atom through two nitrogen atoms in both series. Solution equilibria involving different phenanthroline copper(I) species were studied by 1H and 31P NMR spectroscopy, electrochemistry, and spectroelectrochemistry. The solution specia…

Cadmium Metal–Organic Frameworks Based on Ditopic Triazamacrocyclic Linkers: Unusual Structural Features and Selective CO 2 Capture

International audience; Two three-dimensional cadmium metal organic frameworks with general formula [Cd-2(L-1)(H2O)(3)](NO3)(0.7)(HCOO)(0.2)Br-0.1 (Cd2L1, L-1 = 1,4,7-tris(4-carboxybenzy1)-1,4,7-triazacyclononane) and Cd(HL2)(H2O)(2) (CdL2, L-2 = 1,4,7-tris(3-(4-benzoate)prop-2-yn-1-yl)-1,4,7-triazacydononane) based on 1,4,7-triazacyclononane N-functionalized by different arylcarboxylic acids were prepared under solvothermal conditions and characterized by single crystal X-ray analysis and porosity measurements. The crystal structure of Cd2L1 reveals a cationic net with a bcs topology,. and nodes are constituted by dinuclear cadmium complexes, in which each cadmium atom adopts a hexacoordin…

Synthesis, spectroscopic, and X-ray structural study of aqua-bis(thymine-N 1 ,N 4 )-ethylenediamine copper(II)dihydrate [Cu(Thy) 2 (en)(H 2 O)].2H 2 O

International audience; A new compound of thyminato anions and ethylenediamine with five-coordinate Cu(II) is synthesized. Elemental analysis and spectroscopic techniques (IR, UV-visible) were used to characterize this compound and its crystal structure was determined by single-crystal X-ray diffraction. The crystal structure consists of the neutral mononuclear complex [Cu(Thy)(2)(en)(H2O)]center dot 2H(2)O. The environment around Cu(II) ion exhibits a square pyramidal geometry with two nitrogen atoms of ethylenediamine and two other nitrogen atoms of the monodentate monoanions of thymine building the equatorial plane. The oxygen atom from H2O molecule occupies the apical position. The comp…

Design of new sensitive α,β-unsaturated carbonyl 1,8-naphtalimide fluorescent probes for thiol bioimaging

International audience; We report herein an efficient synthesis of news naphtalimide-based fluorescent derivatives functionalized with an a,(3-unsaturated carbonyl group. Probes were synthesized from reaction of an amino-naphtalimide precursor with maleic anhydride. Photophysical study of fluorescent probes and cells labelling were performed, and showed that the reactive derivatives exhibit rich turn on fluorescence properties in presence of different biological thiol (Glutathione and Cysteine) making these systems a very promising way for thiol bioimaging.

Facile Synthesis and Self‐Assembly of Zinc (2‐Diethoxyphosphorylethynyl)porphyrins

Design of P-Chirogenic Aminophosphine-Phosphinite Ligands at Both Phosphorus Centers: Origin of Enantioselectivities in Pd-Catalyzed Allylic Reactions.

International audience; We have recently patented an unprecedented stereospecific N→O phosphinyl migration process which transforms P-chirogenic aminophosphines into phosphinites. A fine design of aminophosphine phosphinite ligands (AMPP*) derived from ephedrine and bearing a P-chirogenic center either at the aminophosphine or phosphinite moiety, was performed. The synthesis of AMPP* ligands with P-chirogenic aminophosphine moiety was based on the well-established stereospecific reaction of oxazaphospholidine-borane with organolithium reagents, followed by trapping with a chlorophosphine and borane decomplexation. Concurrently, the preparation of AMPP* ligands with P-chirogenic phosphinite …

CCDC 960835: Experimental Crystal Structure Determination

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CCDC 1029334: Experimental Crystal Structure Determination

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CCDC 1029336: Experimental Crystal Structure Determination

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CCDC 1982653: Experimental Crystal Structure Determination

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CCDC 1982657: Experimental Crystal Structure Determination

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CCDC 1405446: Experimental Crystal Structure Determination

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CCDC 1405448: Experimental Crystal Structure Determination

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CCDC 1429795: Experimental Crystal Structure Determination

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CCDC 1982651: Experimental Crystal Structure Determination

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CCDC 1982662: Experimental Crystal Structure Determination

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CCDC 908612: Experimental Crystal Structure Determination

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CCDC 1439080: Experimental Crystal Structure Determination

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CCDC 984745: Experimental Crystal Structure Determination

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CCDC 1042533: Experimental Crystal Structure Determination

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CCDC 1047405: Experimental Crystal Structure Determination

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CCDC 1418779: Experimental Crystal Structure Determination

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CCDC 1583210: Experimental Crystal Structure Determination

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CCDC 1049575: Experimental Crystal Structure Determination

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CCDC 835277: Experimental Crystal Structure Determination

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CCDC 1047403: Experimental Crystal Structure Determination

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CCDC 1982660: Experimental Crystal Structure Determination

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CCDC 952665: Experimental Crystal Structure Determination

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CCDC 1047398: Experimental Crystal Structure Determination

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CCDC 974338: Experimental Crystal Structure Determination

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CCDC 1047410: Experimental Crystal Structure Determination

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CCDC 1539258: Experimental Crystal Structure Determination

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CCDC 974340: Experimental Crystal Structure Determination

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CCDC 1578032: Experimental Crystal Structure Determination

Related Article: Xiaoqin Jiang, Mario L. Naitana, Nicolas Desbois, Valentin Quesneau, Stéphane Brandès, Yoann Rousselin, Wenqian Shan, W. Ryan Osterloh, Virginie Blondeau-Patissier, Claude P. Gros, Karl M. Kadish|2018|Inorg.Chem.|57|1226|doi:10.1021/acs.inorgchem.7b02655

CCDC 1418785: Experimental Crystal Structure Determination

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CCDC 1529941: Experimental Crystal Structure Determination

Related Article: Hervé Feuchter, Guillaume Ortiz, Yoann Rousselin, Alla Bessmertnykh-Lemeune, and Stéphane Brandès|2017|Cryst.Growth Des.|17|3665|doi:10.1021/acs.cgd.7b00217

CCDC 1047408: Experimental Crystal Structure Determination

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CCDC 1850850: Experimental Crystal Structure Determination

Related Article: Alexander Yu. Mitrofanov, Yoann Rousselin, Victor N Khrustalev, Andey V. Cheprakov, Alla Lemeune, Irina P. Beletskaya|2019|Eur.J.Inorg.Chem.|2019|1313|doi:10.1002/ejic.201900004

CCDC 835276: Experimental Crystal Structure Determination

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CCDC 1529942: Experimental Crystal Structure Determination

Related Article: Hervé Feuchter, Guillaume Ortiz, Yoann Rousselin, Alla Bessmertnykh-Lemeune, and Stéphane Brandès|2017|Cryst.Growth Des.|17|3665|doi:10.1021/acs.cgd.7b00217

CCDC 908613: Experimental Crystal Structure Determination

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CCDC 1953273: Experimental Crystal Structure Determination

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CCDC 1982650: Experimental Crystal Structure Determination

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CCDC 990046: Experimental Crystal Structure Determination

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CCDC 2039650: Experimental Crystal Structure Determination

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CCDC 1982668: Experimental Crystal Structure Determination

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CCDC 1418780: Experimental Crystal Structure Determination

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CCDC 974327: Experimental Crystal Structure Determination

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CCDC 1047402: Experimental Crystal Structure Determination

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CCDC 937024: Experimental Crystal Structure Determination

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CCDC 1439078: Experimental Crystal Structure Determination

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CCDC 1822340: Experimental Crystal Structure Determination

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CCDC 1439081: Experimental Crystal Structure Determination

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CCDC 1418767: Experimental Crystal Structure Determination

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CCDC 1418763: Experimental Crystal Structure Determination

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CCDC 1567139: Experimental Crystal Structure Determination

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CCDC 1047394: Experimental Crystal Structure Determination

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CCDC 1439077: Experimental Crystal Structure Determination

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CCDC 1418781: Experimental Crystal Structure Determination

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CCDC 1492959: Experimental Crystal Structure Determination

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CCDC 1994293: Experimental Crystal Structure Determination

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CCDC 1418772: Experimental Crystal Structure Determination

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CCDC 1910519: Experimental Crystal Structure Determination

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CCDC 974334: Experimental Crystal Structure Determination

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CCDC 945040: Experimental Crystal Structure Determination

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CCDC 1982669: Experimental Crystal Structure Determination

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CCDC 1405449: Experimental Crystal Structure Determination

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CCDC 1429794: Experimental Crystal Structure Determination

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CCDC 1982665: Experimental Crystal Structure Determination

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CCDC 1583212: Experimental Crystal Structure Determination

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CCDC 830704: Experimental Crystal Structure Determination

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CCDC 1492957: Experimental Crystal Structure Determination

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CCDC 1825949: Experimental Crystal Structure Determination

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CCDC 1875843: Experimental Crystal Structure Determination

Related Article: Oana Moncea, Juan Casanova-Chafer, Didier Poinsot, Lukas Ochmann, Clève D. Mboyi, Houssein O. Nasrallah, Eduard Llobet, Imen Makni, Molka El Atrous, Stéphane Brandès, Yoann Rousselin, Bruno Domenichini, Nicolas Nuns, Andrey A. Fokin, Peter R. Schreiner, Jean-Cyrille Hierso|2019|Angew.Chem.,Int.Ed.|58|9933|doi:10.1002/anie.201903089

CCDC 1418782: Experimental Crystal Structure Determination

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CCDC 1880078: Experimental Crystal Structure Determination

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CCDC 1418770: Experimental Crystal Structure Determination

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CCDC 1812155: Experimental Crystal Structure Determination

Related Article: Valentin Quesneau, Wenqian Shan, Nicolas Desbois, Stephane Brandes, Yoann Rousselin, Meddy Vanotti, Virginie Blondeau-Patissier, Mario Naitana, Paul Fleurat-Lessard, Eric Van Caemelbecke, Karl M. Kadish, Claude P. Gros|2018|Eur.J.Inorg.Chem.|2018|4265|doi:10.1002/ejic.201800897

CCDC 1418765: Experimental Crystal Structure Determination

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CCDC 1982667: Experimental Crystal Structure Determination

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CCDC 937026: Experimental Crystal Structure Determination

Related Article: Emmanuelle Rémond, Jérôme Bayardon, Shinobu Takizawa, Yoann Rousselin, Hiroaki Sasai, and Sylvain Jugé|2013|Org.Lett.|15|1870|doi:10.1021/ol400515e

CCDC 938729: Experimental Crystal Structure Determination

Related Article: Pawel Jewula, Jean-Claude Berthet, Jean-Claude Chambron, Yoann Rousselin, Pierre Thuéry, Michel Meyer|2015|Eur.J.Inorg.Chem.||1529|doi:10.1002/ejic.201403206

CCDC 974333: Experimental Crystal Structure Determination

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CCDC 1583211: Experimental Crystal Structure Determination

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CCDC 1047411: Experimental Crystal Structure Determination

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CCDC 1047401: Experimental Crystal Structure Determination

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CCDC 1982663: Experimental Crystal Structure Determination

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CCDC 829826: Experimental Crystal Structure Determination

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CCDC 937025: Experimental Crystal Structure Determination

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CCDC 1953272: Experimental Crystal Structure Determination

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CCDC 1479591: Experimental Crystal Structure Determination

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CCDC 1009948: Experimental Crystal Structure Determination

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CCDC 1418776: Experimental Crystal Structure Determination

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CCDC 1830060: Experimental Crystal Structure Determination

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CCDC 1424523: Experimental Crystal Structure Determination

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CCDC 1418784: Experimental Crystal Structure Determination

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CCDC 1047396: Experimental Crystal Structure Determination

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CCDC 1554869: Experimental Crystal Structure Determination

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CCDC 1583209: Experimental Crystal Structure Determination

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CCDC 1405447: Experimental Crystal Structure Determination

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CCDC 831070: Experimental Crystal Structure Determination

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CCDC 889646: Experimental Crystal Structure Determination

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CCDC 974326: Experimental Crystal Structure Determination

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CCDC 924316: Experimental Crystal Structure Determination

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CCDC 974341: Experimental Crystal Structure Determination

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CCDC 983068: Experimental Crystal Structure Determination

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CCDC 1982654: Experimental Crystal Structure Determination

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CCDC 974324: Experimental Crystal Structure Determination

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CCDC 1047399: Experimental Crystal Structure Determination

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CCDC 1830057: Experimental Crystal Structure Determination

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CCDC 1429796: Experimental Crystal Structure Determination

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CCDC 990049: Experimental Crystal Structure Determination

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CCDC 1982658: Experimental Crystal Structure Determination

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CCDC 1418769: Experimental Crystal Structure Determination

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CCDC 974325: Experimental Crystal Structure Determination

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CCDC 941426: Experimental Crystal Structure Determination

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CCDC 1418774: Experimental Crystal Structure Determination

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CCDC 1053706: Experimental Crystal Structure Determination

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CCDC 1439082: Experimental Crystal Structure Determination

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CCDC 937023: Experimental Crystal Structure Determination

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CCDC 1418783: Experimental Crystal Structure Determination

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CCDC 1825950: Experimental Crystal Structure Determination

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CCDC 990047: Experimental Crystal Structure Determination

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CCDC 1476682: Experimental Crystal Structure Determination

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CCDC 1910517: Experimental Crystal Structure Determination

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CCDC 1982659: Experimental Crystal Structure Determination

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CCDC 1418771: Experimental Crystal Structure Determination

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CCDC 976071: Experimental Crystal Structure Determination

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CCDC 1910516: Experimental Crystal Structure Determination

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CCDC 1047412: Experimental Crystal Structure Determination

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CCDC 1047404: Experimental Crystal Structure Determination

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CCDC 974328: Experimental Crystal Structure Determination

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CCDC 1583208: Experimental Crystal Structure Determination

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CCDC 1042608: Experimental Crystal Structure Determination

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CCDC 990045: Experimental Crystal Structure Determination

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CCDC 1439079: Experimental Crystal Structure Determination

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CCDC 1479590: Experimental Crystal Structure Determination

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CCDC 1047409: Experimental Crystal Structure Determination

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CCDC 907927: Experimental Crystal Structure Determination

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CCDC 931678: Experimental Crystal Structure Determination

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CCDC 937567: Experimental Crystal Structure Determination

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CCDC 960361: Experimental Crystal Structure Determination

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CCDC 1053707: Experimental Crystal Structure Determination

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CCDC 1476683: Experimental Crystal Structure Determination

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CCDC 1476681: Experimental Crystal Structure Determination

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CCDC 937568: Experimental Crystal Structure Determination

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CCDC 1047406: Experimental Crystal Structure Determination

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CCDC 1982666: Experimental Crystal Structure Determination

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CCDC 1047407: Experimental Crystal Structure Determination

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CCDC 1479592: Experimental Crystal Structure Determination

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CCDC 1825951: Experimental Crystal Structure Determination

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CCDC 1418766: Experimental Crystal Structure Determination

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CCDC 974336: Experimental Crystal Structure Determination

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CCDC 1830059: Experimental Crystal Structure Determination

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CCDC 974335: Experimental Crystal Structure Determination

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CCDC 1418764: Experimental Crystal Structure Determination

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CCDC 960834: Experimental Crystal Structure Determination

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CCDC 1447439: Experimental Crystal Structure Determination

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CCDC 1054357: Experimental Crystal Structure Determination

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CCDC 1418775: Experimental Crystal Structure Determination

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CCDC 2039652: Experimental Crystal Structure Determination

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CCDC 908614: Experimental Crystal Structure Determination

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CCDC 975958: Experimental Crystal Structure Determination

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CCDC 1579042: Experimental Crystal Structure Determination

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CCDC 1047400: Experimental Crystal Structure Determination

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CCDC 1009991: Experimental Crystal Structure Determination

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CCDC 990048: Experimental Crystal Structure Determination

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CCDC 974337: Experimental Crystal Structure Determination

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CCDC 1418762: Experimental Crystal Structure Determination

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CCDC 1982661: Experimental Crystal Structure Determination

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CCDC 952664: Experimental Crystal Structure Determination

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CCDC 1447438: Experimental Crystal Structure Determination

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CCDC 1910518: Experimental Crystal Structure Determination

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CCDC 1910052: Experimental Crystal Structure Determination

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CCDC 1492958: Experimental Crystal Structure Determination

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CCDC 1910515: Experimental Crystal Structure Determination

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CCDC 974329: Experimental Crystal Structure Determination

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CCDC 960359: Experimental Crystal Structure Determination

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CCDC 2063384: Experimental Crystal Structure Determination

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CCDC 1982664: Experimental Crystal Structure Determination

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CCDC 945039: Experimental Crystal Structure Determination

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CCDC 1815709: Experimental Crystal Structure Determination

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CCDC 1583213: Experimental Crystal Structure Determination

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CCDC 1994294: Experimental Crystal Structure Determination

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CCDC 1431598: Experimental Crystal Structure Determination

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CCDC 902497: Experimental Crystal Structure Determination

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CCDC 1053708: Experimental Crystal Structure Determination

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CCDC 1418773: Experimental Crystal Structure Determination

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CCDC 1405500: Experimental Crystal Structure Determination

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CCDC 1418768: Experimental Crystal Structure Determination

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CCDC 976101: Experimental Crystal Structure Determination

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CCDC 1825952: Experimental Crystal Structure Determination

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CCDC 1429797: Experimental Crystal Structure Determination

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CCDC 908617: Experimental Crystal Structure Determination

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CCDC 1047395: Experimental Crystal Structure Determination

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CCDC 952663: Experimental Crystal Structure Determination

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CCDC 1819713: Experimental Crystal Structure Determination

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CCDC 908616: Experimental Crystal Structure Determination

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CCDC 1042532: Experimental Crystal Structure Determination

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CCDC 1054356: Experimental Crystal Structure Determination

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CCDC 990050: Experimental Crystal Structure Determination

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CCDC 974339: Experimental Crystal Structure Determination

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CCDC 952662: Experimental Crystal Structure Determination

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CCDC 1047397: Experimental Crystal Structure Determination

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CCDC 835275: Experimental Crystal Structure Determination

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CCDC 1029335: Experimental Crystal Structure Determination

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