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

Electrochemical and spectroscopic studies of poly(diethoxyphosphoryl)porphyrins

Abstract The synthesis and electrochemical characterization of two related series of porphyrins bearing diethoxyphosphoryl groups are reported. One group of compounds is represented as (T( p -R)PP)M where R = phos = P(O)(OEt) 2 and M = Zn(II) or H 2 while the other is represented as (di( p -R)Pdi(phos)P)M where R = P(O)(OEt) 2 , H or CH 3 and M = Zn(II) or H 2 . Each porphyrin was investigated by electrochemistry and thin-layer spectroelectrochemistry in CH 2 Cl 2 , CDCl 3 , CHCl 3 or PhCN containing tetra- n -butylammonium perchlorate (TBAP) as supporting electrolyte. The highly electron-withdrawing P(O)(OEt) 2 groups lead to easier reductions and harder oxidations than the two comparison …

On the synthesis of functionalized porphyrins and porphyrin conjugates via β-aminoporphyrins

International audience; The synthesis of functionalized porphyrins and their conjugates from meso-tetraarylporphyrins through the acylation and the oxidation of beta-aminoporphyrins was investigated. 2,3-Dioxochlorins were prepared by the oxidation of a variety of beta-aminoporphyrins and subsequently used in a condensation reaction with functionalized aromatic aldehydes and ammonium acetate to form beta-functionalized porphyrins bearing a fused imidazole ring. Under optimized experimental conditions both reactions tolerate various functional groups and afford the products in an appropriate overall yield. The mildness and usefulness of this methodology are illustrated by several examples in…

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…

Post-synthetic methods for functionalization of imidazole-fused porphyrins

Several methods for the post-synthetic modification of imidazo[4,5-[Formula: see text]]porphyrins are reported. First, a synthetic approach to the isomeric difunctionalized porphyrins, containing two [Formula: see text]-fused 2-aryl-1[Formula: see text]-imidazole cycles at adjacent or opposite pyrrole rings of the macrocycle is developed. The core chemistry of this synthetic route is the transformation of 2-aryl-1[Formula: see text]-imidazo[4,5-[Formula: see text]]porphyrins into corresponding imidazodioxochlorins followed by Debus–Radziszewski condensation with aromatic aldehyde. Next, 2-(4-bromophenyl)-1[Formula: see text]-imidazo[4,5-[Formula: see text]]-5,10,15,20-tetramesitylporphyrin…

Platinum( ) and palladium( ) complexes with electron-deficient -diethoxyphosphorylporphyrins: synthesis, structure and tuning of photophysical properties by varying peripheral substituents

The luminescence quenching by O and photodegradation of Pt( ) and Pd( ) phosphorylporphyrins are reported.

Synthesis of (trans-A2)BC-Type Porphyrins with Acceptor Diethoxyphosphoryl and Various Donor Groups and their Assembling in the Solid State and at Interfaces

Design and evaluation of sensory systems based on amphiphilic anthraquinones molecular receptors

A new paradigm is described that allows one to create different types of sensors: from highly sensitive ones to practical household devices. Our approach relies on modular molecular receptors incorporating an intensely-colored aminoanthraquinone signaling unit equipped with both hydrophilic and hydrophobic modules, the number and size of which being configured in accordance with the targeted analyte and the sought detection method. An important advantage is the compliance with some principles of green chemistry, avoiding the use of toxic organic solvents. The proper functionalization of the anthraquinone scaffold afforded water-soluble chromoinophores capable of quantifying selectively Hg2+…

Imidazoporphyrins as supramolecular tectons: synthesis and self-assembly of zinc 2-(4-pyridyl)-1H-imidazo[4,5-b]porphyrinate

International audience; 5,10,15,20-Tetramesityl-2-(4-pyridyl)-1H-imidazo[4,5-b]porphyrin (PyPor) bearing a pyridine donor site connected to the tetrapyrrolic macrocycle by a rigid imidazole linker was prepared in high yield by the condensation of the corresponding 2,3-dioxochlorin and 4-formylpyridine in the presence of ammonium acetate. After the insertion of a metal ion capable of metal–ligand axial coordination, namely Zn(II), this compound afforded self-complementary porphyrin PyPorZn which was suitable for self-assembly. In the crystals, this complex exists as a zigzag coordination polymer formed through the axial coordination of the pyridine nitrogen atom to the zinc ion of the neighb…

Optical methods for the detection of heavy metal ions

The review covers an important area of the modern chemistry, namely, the detection of heavy metal ions using optical molecular detectors. The role of this method in metal ion detection and the physicochemical grounds of operation of chemosensors are discussed, and examples of detection of most abundant heavy metal ions and synthetic approaches to molecular detectors are presented. The immobilization of molecular detectors on solid substrates for the design of analytical sensor devices is described. The bibliography includes 178 references.

Coordination self-assembly through weak interactions in meso-dialkoxyphosphoryl-substituted zinc porphyrinates.

International audience; The self-assembly of seven zinc 10-(dialkoxyphosphoryl)-5,15-diarylporphyrinates Zn5-Zn11 containing different substituents at the phosphonate and aryl groups was investigated. Single crystals of Zn5-Zn9 complexes were grown under the same conditions and analyzed by X-ray structural analysis. A supramolecular self-assembly is observed in all crystals through weak coordinative bonding of the phosphoryl group of one porphyrin molecule to the zinc(II) ion of a second porphyrin molecule. The geometry of the porphyrin macrocycle is similar in all of the studied crystals and the central zinc atom in each case adopts a distorted tetragonal pyramidal environment. However, th…

Immobilization of copper complexes with (1,10-phenanthrolinyl)phosphonates on titania supports for sustainable catalysis

Different strategies for the immobilization of copper complexes with 1,10-phenanthroline (phen) using the phosphonate anchoring group were investigated to prepare robust and porous heterogeneous catalysts. Homoleptic and heteroleptic copper(I) complexes with phen bearing the bis(trimethylsiloxy)phosphoryl anchoring group (Pphen-Si) at different positions of the phen backbone were prepared and covalently incorporated into titania (TiO2) xerogels by using the sol–gel process or grafted onto the surface of mesoporous TiO2 (SBET = 650 m2 g−1). Copper(I) bis(Pphen-Si) complexes were the only complexes that were successfully anchored onto the TiO2 surface because the heterogenization was often ac…

Heterocycle-appended porphyrins: synthesis and challenges

Abstract Porphyrin and their versatile metal complexes represent a special class of coordination compounds possessing unique physical-chemical properties. The achievements in the development of the synthetic approaches for the modification of the porphyrin macrocycle allowed the preparation of a variety of functional derivatives for diverse applications. Among a broad diversity of synthetically available metalloporphyrins meso-substituted tetrapyrroles are comprehensively investigated. However, β-substituted porphyrins could be considered as the most suitable models for mimicking the key roles of naturally occurring dyes in vital processes. The introduction of various substituents to the β-…

Synthesis of porphyrin-bis(polyazamacrocycle) triads via Suzuki coupling reaction

Suzuki–Miyaura cross-coupling reaction has been used for the synthesis of tricyclic architectures based on trans-A2B2-porphyrins and bisaminal-protected polyazamacrocycles which are linked directly or by a p-phenylene spacer. This modular approach allowed the synthesis of ligands with various substituted porphyrin macrocycles and bisaminal-protected tetraazamacrocycles possessing different cavity sizes. These molecules can be assembled into dimers using a DABCO linker. Deprotection of these compounds afforded porphyrin-bis(polyazamacrocycle) triads.

Insights into the Synthesis and the Solution Behavior ofmeso-Aryloxy- and Alkoxy-Substituted Porphyrins

meso-RO-appended (R = alkyl, aryl) porphyrins bearing one or two OR substituents at the tetrapyrrolic macrocycle were synthesized in good yields from 5,15-dibromo-10,20-diphenylporphyrins 2H(Br2DPP), Ni(Br2DPP) and Zn(Br2DPP) using an SNAr reaction. By varying the solvent, the base, the temperature, and the time of the reaction, the optimum conditions were established, and the selective introduction of one or two meso-RO substituents at the periphery of the macrocycle was achieved. Moreover, monofunctionalization of Ni(Br2DPP) according to an SNAr reaction was used as a key step for the synthesis of rarely explored unsymmetrical porphyrinyl alkyl ethers. 1H NMR studies of these ethers in CD…

Insights into the crystal packing of phosphorylporphyrins based on the topology of their intermolecular interaction energies

Four metal complexes of 5,15-bis(diethoxyphosphoryl)-10,20-diphenylporphyrin 1M (M = Cd(II), Ni(II), Pd(II), and Pt(II)) were synthesized and crystallographically characterized. The crystal organization patterns were analyzed using DFT (B97-D3/def2-SVP) calculations of the intermolecular interaction energies between complexes in the crystals. For the systematic analysis of crystal packing, the calculations were extended to previously reported compounds 1M (M = H2, Cu(II), and Zn(II)). Quantitative analysis of the interaction energies shows the essential role of weak intermolecular interactions, such as C-H⋯O, C-H⋯π and M⋯π, in the formation of basic structural motifs and their organization …

Exploiting Palladium-Catalyzed Cross-Coupling for the Synthesis of 2-Aryl-Substituted 1-Aminocyclopropylphosphonates

A series of 2-aryl-substituted 1-aminocyclopropylphosphonates containing an additional remote phosphonate group have been synthesized starting from readily accessible dimethyl (1 R *,2 R *)-2-(4-bromophenyl)-1-formamidocyclopropylphosphonate using cross-coupling methodology. Different types of palladium-catalyzed reactions for carbon–carbon and carbon–phosphorus bond formation were realized. In each case the optimum conditions were found to obtain the desired products in high yield in both small- and large-scale experiments.

A metal-responsive interdigitated bilayer for selective quantification of mercury( ii ) traces by surface plasmon resonance

Reusable surface plasmon resonance chips allowing the quantitative and selective detection of mercury(II) ions in water at the 0.01 nM level are reported. The surface-modified gold sensor consists of a rarefied self-assembled monolayer of octanethiol topped with a Langmuir–Blodgett monolayer of an amphiphilic and highly-specific chelator. The interdigitated architecture confers to the bilayer a high packing density, surface coverage, and binding-group accessibility.

6-Polyamino-substituted quinolines: synthesis and multiple metal (CuII, HgIIand ZnII) monitoring in aqueous media

Chemoselective palladium-catalyzed arylation of polyamines with 6-bromoquinoline has been explored to prepare chelators for the detection of metal cations in aqueous media. The introduction of a single aromatic moiety into non-protected polyamine molecules was achieved using the commercially available Pd(dba)2/BINAP precatalyst to afford nitrogen chelators, in which the aromatic signalling unit is directly attached to the polyamine residue. Water-soluble receptors were then synthesized using N-alkylation of these polyamines by hydrophilic coordinating residues. By combining rich photophysical properties of the 6-aminoquinoline unit with a high coordination affinity of chelating polyamines a…

Gallium(III) and Indium(III) Complexes with meso-Monophosphorylated Porphyrins: Synthesis and Structure. A First Example of Dimers Formed by the Self-Assembly of meso-Porphyrinylphosphonic Acid Monoester

International audience; The synthesis and structural characterization, both in solution by means of H-1 and P-31 NMR and UV-vis spectroscopies and in the solid state by X-ray diffraction on single crystal, of a series of gallium(III) and indium(III) meso-mono(diethoxyphosphoryl)porphyrins bearing different peripheral substituents as well as the corresponding monoesters and phosphonic acids are reported. This work describes the first example of the X-ray structure of a self-assembled dimer formed via strong binding between the oxygen atom of the phosphonate substituent and the gallium(III) cations of adjacent porphyrin molecules [Ga-O = 1.9708(13) angstrom].

Ultra-thin film sensors based on porphyrin-5-ylphosphonate diesters for selective and sensitive dual-channel optical detection of mercury(II) ions

International audience; Reusable dual-channel optical sensors for Hg2+ ions were prepared by Langmuir-Schaefer (LS) method from amphiphilic (trans-A2)BC-type porphyrins functionalized at meso-positions of the tetrapyrrolic macrocycle by sterically demanding diethoxyphosphoryl and mesityl groups as well as electron donating RO, RS or RNH substituents (R = n-C8H17). These three novel amphiphilic porphyrin derivatives were synthesized in good yields and their floating films at the air⎯water interface were investigated. In these monolayers, porphyrin molecules display a slipped stack-of-card orientation, but their strong π stacking is prohibited by bulky diethoxyphosphoryl and mesityl groups. T…

Cu(I) complexes with diethoxyphosphoryl-1,10-phenanthrolines in catalysis of C–C and C–heteroatom bonds formation

Abstract Diethoxyphosphoryl substituted 1,10-phenanthroline copper(I) complexes were tested as catalysts in the Sonogashira-type reaction, α-arylation of phosphoryl-stabilized C–H acids, C–N, C–P bond forming reactions (substitution reactions) and in the reaction of phenylacetylene and bis(pinacolato)diboron (addition reaction). The complexes demonstrate fairly high catalytic activity and in some cases their efficiency is superior to that of the parent Cu(phen)(PPh 3 )Br (phen = phenanthroline).

Electrochemical, Spectroelectrochemical, and Structural Studies of Mono- and Diphosphorylated Zinc Porphyrins and Their Self-Assemblies

International audience; Three series of porphyrins containing a Zn(II) central metal ion and zero, one or two phosphoryl groups at the meso-positions of the macrocycle were characterized as to their electrochemical, spectroscopic and structural properties in non-aqueous media. The investigated compounds are represented as 5,15-bis(4'-R-phenyl)porphyrinatozinc, 10-(diethoxyphosphoryl)-5,15-bis(4'-R-phenyl)porphyrinatozinc and 5,15-bis(diethoxyphosphoryl)-10,20-bis(4'-R-phenyl)porphyrinatozinc, where R = OMe, Me, H or CN. Linear-free energy relationships are observed between the measured redox potentials at room temperature and the electronic nature of the substituents at the 5 and 15 meso-ph…

Electrochemical and Spectroelectrochemical Studies of Diphosphorylated Metalloporphyrins. Generation of a Phlorin Anion Product

Two series of diphosphoryl-substituted porphyrins were synthesized and characterized by electrochemistry and spectroelectrochemistry in nonaqueous media containing 0.1 M tetra-n-butylammonium perchlorate (TBAP). The investigated compounds are 5,15-bis(diethoxyphosphoryl)-10,20-diphenylporphyrins (Ph)2(P(O)(OEt)2)2PorM and 5,15-bis(diethoxyphosphoryl)-10,20-di(para-carbomethoxyphenyl)porphyrins (PhCOOMe)2(P(O)(OEt)2)2PorM where M = 2H, Co(II), Ni(II), Cu(II), Zn(II), Cd(II), or Pd(II). The free-base and five metalated porphyrins with nonredox active centers undergo two ring-centered oxidations and two ring-centered reductions, the latter of which is followed by a chemical reaction of the por…

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)…

Unusual Formation of a Stable 2D Copper Porphyrin Network

Copper(II) 5,15-bis(diethoxyphosphoryl)-10,20-diphenylporphyrin was obtained and characterized by means of cyclic voltammetry, electron paramagnetic resonance, Fourier transform infrared, and UV-visible spectroscopy. Three crystalline forms were grown and studied by means of X-ray diffraction methods (single crystal and powder). The highly electron-withdrawing effect of phosphoryl groups attached directly to the porphyrin macrocycle results in a self-assembling process, with formation of a stable 2D coordination network, which is unusual for copper(II) porphyrins. The resulting 2D structure is a rare example of an assembly based on copper(II) porphyrins where the copper(II) central metal io…

Electrochemical and spectroelectrochemical studies of β-phosphorylated Zn porphyrins

The electrochemical and spectroelectrochemical properties of two β-phosphorylated Zn porphyrins, [2-diethoxyphosphoryl-5,10,15,20-tetraphenylporphyrinato]zinc (1) and [2-diisopropoxyphosphoryl-5,10,15,20-tetraphenylporphyrinato]zinc (2), are reported in CH 2 Cl 2 and PhCN containing tetrabutylammonium perchlorate (TBAP) or tetrabutylammonium hexafluorophosphate (TBAPF6) as supporting electrolyte. Under certain solution conditions, three one-electron reductions are observed, with the last process being attributed to the product of a chemical reaction following formation of the porphyrin dianion. Two or three oxidations are observed for the same compounds, again depending upon the solution c…

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…

Supramolecular Assembly of Organophosphonate Diesters Using Paddle-Wheel Complexes: First Examples in Porphyrin Series

The reactions of dicopper tetrapivalate complex Cu2(μ-OOC-t-Bu)4(NCMe)2 (1) with triphenylphosphine oxide and diethyl phosphite allow paddle-wheel (PW) copper(II) complexes with phosphorus-containing axial ligands (2, 3) to be obtained. When meso-bis(diethoxyphosphoryl)porphyrins 4M were employed in this ligand exchange reaction, a series of one-dimensional (1D) homo- and heterometallic coordination polymers 5M composed of PW subunits and organophosphonate diesters were prepared and characterized by means of single crystal X-ray analysis. Planar porphyrinate 4Pd and nonplanar metalloporphyrinates 4Cu and 4Ni proved to be appropriate molecular structural blocks for assembly of coordination p…

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

CCDC 902786: Experimental Crystal Structure Determination

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CCDC 1017124: Experimental Crystal Structure Determination

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CCDC 1529941: Experimental Crystal Structure Determination

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CCDC 1529942: Experimental Crystal Structure Determination

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CCDC 1871295: Experimental Crystal Structure Determination

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CCDC 990046: Experimental Crystal Structure Determination

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CCDC 902785: Experimental Crystal Structure Determination

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CCDC 1844989: Experimental Crystal Structure Determination

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CCDC 1904438: Experimental Crystal Structure Determination

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CCDC 945040: Experimental Crystal Structure Determination

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CCDC 1844993: Experimental Crystal Structure Determination

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CCDC 1017125: Experimental Crystal Structure Determination

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CCDC 998788: Experimental Crystal Structure Determination

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CCDC 1890813: Experimental Crystal Structure Determination

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CCDC 1017126: Experimental Crystal Structure Determination

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CCDC 1017127: Experimental Crystal Structure Determination

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CCDC 1844991: Experimental Crystal Structure Determination

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CCDC 1017128: Experimental Crystal Structure Determination

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CCDC 990049: Experimental Crystal Structure Determination

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CCDC 1017130: Experimental Crystal Structure Determination

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CCDC 990047: Experimental Crystal Structure Determination

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CCDC 902787: Experimental Crystal Structure Determination

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