Tuning of interfacial charge transport in polyporphine/phthalocyanine heterojunctions by molecular geometry control for an efficient gas sensor
Abstract Owing to high interfacial conductivity, organic heterostructures hold great promises to augment the electrical performances of electronic devices. In this endeavor, the present work reports fabrication of novel polyporphine/phthalocyanine heterostructures and investigates the modulation of charge transport induced by structural change of polyporphine and its implication on ammonia sensing properties. Polyporphines materials are electrosynthesized by oxidation of zinc(II) porphine monomer that corresponds to the fully unsubstituted porphyrin. At less-positive anodic potential, low conducting meso,meso-singly-linked type-1 polymer (pZnP-1) is formed in which a monomer unit stays orth…
Electrosynthesis and X‐ray Crystallographic Structure of Zn II meso ‐Triaryltriphenylphosphonium Porphyrin and Structural Comparison with Mg II meso ‐Triphenylphosphonium Porphine
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…
Electroactive polymeric material with condensed structure on the basis of magnesium(II) polyporphine
International audience; Previous publication of the authors presented evidences that electroch emical oxidation of Mg(II) porphine (fully unsubstituted porphyrin, MgP) in acetonitrile (AN) at a very low potential leads to deposition of films at electrode surface corresponding to typical electroactive polymers, with their reversible transition betwee n the electronconducting and insulating states depending on the electrode potential/oxidation level ("film of type I"). It is demonstrated in the actual publication that these films in contact with a monomer-free solution are subject to an irreversible transformation to quite a different material ("film of type II") under the influence of a high…
Magnesium(II) polyporphine: The first electron-conducting polymer with directly linked unsubstituted porphyrin units obtained by electrooxidation at a very low potential
Abstract Electrooxidation of magnesium(II) porphine, a totally unsubstituted porphyrin, in acetonitrile solution under potentiostatic or potentiodynamic regime leads to a polymer film at the electrode surface. Polymer deposition takes place at extremely low potential, several hundred mV less positive even compared to the deposition potential for pyrrole or EDOT (at identical monomer concentrations) in the same solvent. Film thickness can be controlled by the passed deposition charge. This material and its THF-soluble fraction have been characterized by various electrochemical methods as well as by UV–visible and IR spectroscopies, XPS, XRD and MALDI-TOF techniques. This analysis has allowed…
ChemInform Abstract: Electrosynthesis of Imidazolium Carboxylates.
For the first time the synthesis of imidazolium carboxylates is efficiently achieved by electrochemical reduction of imidazolium salts under very mild conditions.
Synthesis and characterization of novel quinolyl porphyrins as receptors. Study of their association with halophenols and 4nitrophenol as a reference
International audience; In this work, new receptors built on the porphyrin scaffold were synthesized for halophenols recognition. A quinolyl group was introduced on the porphyrin's periphery as binding site, to form two series of molecules based on two distinct porphyrin frames and which were obtained in free base and zinc forms. The binding between these porphyrin based receptors and halophenols (2,3,4,6tetrachlorophenol, 2,4,6-trichlorophenol or 2,4,6-tribromophenol) was studied. As established by 1 H NMR spectroscopy, the binding constants are in the range of two-digit numbers, which value is correlated with the porphyrin structure (substitutive pattern, form of the free base or Zn II co…
Electrosynthesis of imidazolium carboxylates.
Synthesis of imidazolium carboxylate compounds was efficiently achieved by electrochemical reduction of imidazolium precursors under very mild conditions.
Synthesis of new electroactive polymers by ion-exchange replacement of Mg(II) by 2H+ or Zn(II) cations inside Mg(II) polyporphine film, with their subsequent electrochemical transformation to condensed-structure materials
Abstract It has been demonstrated that the treatment of the magnesium polyporphine of type I, pMgP-I, by trifluoroacetic acid in acetonitrile may be used to replace initial central Mg(II) cations inside the monomeric macrocycle units by protons, to get a new electroactive polymer, “free-base polyporphine of type I”, pH2P-I. In its turn, these inserted protons may be replaced by Zn(II) cations via the film treatment with zinc acetate in organic solvent, to get another new electroactive polymer, “zinc polyporphine of type I”, pZnP-I. These changes of central ions inside monomer units manifest themselves by characteristic modifications of their electroactive properties as well as of UV–visible…
A glassy carbon electrode modified by a triply-fused-like Co( ii ) polyporphine and its ability for sulphite oxidation and detection
This article presents a Co(II) polyporphine conductive polymer easily and rapidly obtained (less than 2 h 30 min) on the surface of a glassy carbon electrode from the transformation of an initial Mg(II) porphine solution in a four-step process (including electrochemical and chemical stages). The intimate molecular structure is argued on the basis of the electrochemical response of the modified electrode, as well as its surface characterization. Owing to its apparent stability in water over potential cycling and its high density in active Co(II) centers, the electrosynthesized film shows its ability to catalyze sulphite oxidation in aqueous solutions. The mechanism of this molecular catalysi…
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 …
Crystallographic, spectroscopic and electrochemical characterization of pyridine adducts of magnesium(II) and zinc(II) porphine complexes
Abstract A new purification method of magnesium(II) and zinc(II) porphine complexes (MgP and ZnP, respectively) by crystallization of their respective pyridine adducts is described. Pure MgP and ZnP can be regenerated by removal of the coordinated pyridine ligands by heating at 200 °C under vacuum. X-ray crystallographic structures of the pyridine adducts are presented for the first time. NMR analyses of the adducts reveal the coordination of two pyridine molecules. Electrochemical as well as UV-vis absorption spectroscopy analyses in DMF of MgP·(Py)2, ZnP·(Py)2, MgP and ZnP indicate that pyridine adducts are totally dissociated. Besides, oxidation peaks of these complexes are totally irrev…
Control over the oxidative reactivity of metalloporphyrins. Efficient electrosynthesis of meso,meso-linked zinc porphyrin dimer.
The electrochemical oxidation of zinc(II) 5,15-p-ditolyl-10-phenylporphyrin at its first oxidation potential leads to the formation of the corresponding meso-meso porphyrin dimer as the main product. The number of electrons abstracted, the addition of the hindered base 2,6-lutidine as well as operating in DMF, instead of a CH(2)Cl(2)/CH(3)CN mixture are the key parameters to obtain high yields of the desired coupling product. Indeed, when the electrolyses are carried out in the CH(2)Cl(2)/CH(3)CN mixture, the unexpected zinc(II) 5-chloro-10,20-p-ditolyl-15-phenyl porphyrin is produced as a by-product, the chlorine atom originating from the CH(2)Cl(2) solvent. The monomer and the dimer are c…
Aromatic Nucleophilic Substitution (SNAr) of meso-Nitroporphyrin with Azide and Amines as an Alternative Metal Catalyst Free Synthetic Approach To Obtain meso-N-Substituted Porphyrins
International audience; Aromatic nucleophilic substitution reaction of the nitro group of meso-nitroporphyrins with azide and various amines was achieved and represents an alternative procedure to C-N coupling reactions usually needed to obtain such meso-N-substituted porphyrins in good yields.
Electropolymerization of non-substituted Mg(II) porphine: Effects of proton acceptor addition
Abstract Electropolymerization of unsubstituted magnesium porphine in acetonitrile solutions possessing various proton-accepting properties has been studied. The overall rate of the polymer-product accumulation on the electrode surface has been established to be limited by the deprotonation step of intermediate species. This conclusion is based on the observed influence of proton-accepting additives, water or 2,6-dimethylpyridine (lutidine), on the Mg-porphine electrooxidation process. Lutidine addition into the polymerization bath enables one to enhance strongly the rate of the film growth and the efficiency of this process increases more than by a factor of two, redox, electric conductivi…
Tuning the Electrochemistry of Free-Base Porphyrins in Acidic Nonaqueous Media: Influence of Solvent, Supporting Electrolyte, and Ring Substituents
International audience; A detailed study of reduction potentials, electroreduction mechanisms and acid-base chemistry was carried out on two series of free-base porphyrins in nonaqueous media. The first series is represented by four-pyrrole substituted tetraphenylporphyrin (TPP) derivatives, two of which are planar and two of which are nonplanar in their non-protonated form. The second comprises porphyrins with 0-4 meso-phenyl groups on the macrocycle. Equilibrium constants for conversion of each neutral porphyrin to its diprotic [H4P] 2+ form were determined and the electrochemistry was then elucidated as a function of: (i) type of nonaqueous solvent, (ii) anion of supporting electrolyte, …
Kinetic and Electrochemical Studies of the Oxidative Addition of Demanding Organic Halides to Pd(0): the Efficiency of Polyphosphane Ligands in Low Palladium Loading Cross-Couplings Decrypted
International audience; Oxidative addition (OA) of organic halides to palladium(0) species is a fundamental reaction step which initiates the C–C bond formation catalytic processes typical of Pd(0)/Pd(II) chemistry. The use of structurally congested polyphosphane ligands in palladium-catalyzed C–C bond formation has generated very high turnover numbers (TONs) in topical reactions such as Heck, Suzuki, Sonogashira couplings, and direct sp2C–H functionalization. Herein, the OA of aryl bromides to Pd(0) complexes stabilized by ferrocenylpolyphosphane ligands L1 (tetraphosphane), L2 (triphosphane), and L3 (diphosphane) is considered. The investigation of kinetic constants for the addition of Ph…
Gold(I) Complexes Nuclearity in Constrained Ferrocenyl Diphosphines: Dramatic Effect in Gold‐Catalyzed Enyne Cycloisomerization
International audience; Di-tert-butylated-bis(phosphino)ferrocene ligands bearing phosphino substituents R (R=phenyl, cyclohexyl, isopropyl, mesityl, or furyl) allow tuning the selective formation of Au(I) halide complexes. Thus, dinuclear linear twocoordinate, but also rare mononuclear trigonal three-coordinate and tetrahedral four-coordinate complexes were formed upon tuning of the conditions. Both Au(I) chloride and rarer Au(I) iodide complexes were synthesized, and their X-ray diffraction analysis are reported. The significance of the control of structure and nuclearity in Au(I) complexes is further illustrated herein by its strong effect on the efficiency and selectivity of gold-cataly…
Identification of Three-Way DNA Junction Ligands through Screening of Chemical Libraries and Validation by Complementary in Vitro Assays
International audience; The human genome is replete with repetitive DNA sequences that can fold into thermodynamically stable secondary structures such as hairpins and quadruplexes. Cellular enzymes exist to cope with these structures whose stable accumulation would result in DNA damage through interference with DNA transactions such as transcription and replication. Therefore, the chemical stabilization of secondary DNA structures offers an attractive way to foster DNA transaction-associated damages to trigger cell death in proliferating cancer cells. While much emphasis has been recently given to DNA quadruplexes, we focused here on three-way DNA junctions (TWJ) and report on a strategy t…
BODIPY–diketopyrrolopyrrole–porphyrin conjugate small molecules for use in bulk heterojunction solar cells
Two small molecules denoted as BD-pPor and BD-tPor composed of a central BODIPY core surrounded with two DPP and two porphyrin units have been designed and synthesized. In BD-pPor and BD-tPor, porphyrins are linked to the central BODIPY by phenyl and thiophene bridges, respectively. The optical and electrochemical properties were systematically investigated in order to employ them as donors along with PC71BM as an acceptor for solution processed bulk heterojunction organic solar cells. After the optimization of the active layer, the organic solar cells based on BD-pPor and BD-tPor exhibit overall power conversion efficiencies of 6.67% and 8.98% with an energy loss of 0.63 eV and 0.50 eV. Th…
Synthesis and characterization of zinc carboxy–porphyrin complexes for dye sensitized solar cells
Two zinc porphyrins, 2 and 8, have been synthesized. Porphyrin 8 displays better electronic communication between the dye and the TiO2 electrode. Photophysical measurements and electrochemistry experiments suggest that both porphyrins are very promising sensitizers for dye-sensitized solar cells (DSSCs). It was found that their molecular orbital energy levels favor electron injection and dye regeneration in DSSCs. Solar cells sensitized by 2 and 8 were fabricated, and it was found that they show power conversion efficiencies (PCEs) of 5.27% and 7.13%, respectively. Photovoltaic measurements (J–V curves) together with the incident photon-to-electron conversion efficiency spectra of the two c…
Versatile redox reactivity of triaryl-meso-substituted Ni(ii) porphyrin
The electrochemical oxidation of nickel(II) 5,15-p-ditolyl-10-phenylporphyrin (1-Ni) leads to the formation of different coupling products, with the distribution depending on the nature of the solvent (CH2Cl2–CH3CN, CH2Cl2, DMF), the cell configuration (2 or 3 compartments) and the number of electrons abstracted. In a two compartment configuration (anode and cathode in the same compartment) in a CH2Cl2–CH3CN mixture, nickel(II) 5-chloro-10,20-p-ditolyl-15-phenylporphyrin (1-Ni-Cl) was isolated in good yield and its mechanism of formation is proposed. Switching to the three compartment configuration, the meso-β/meso-β doubly fused dimer (3-Ni) is detected as the major product whereas in pure…
Electrochemistry as an Attractive and Effective Tool for the Synthesis and Immobilization of Porphyrins on an Electrode Surface
Magnesium(II) 10-phenyl-5,15-p-ditolylporphyrin is easily and cleanly transformed by electrolysis. A nitro group is first introduced at the free meso position by anodic substitution. Hydrogenation into the amine is then carried out electrocatalytically under ambient conditions with water as a hydrogen supplier. The synthesized porphyrin under the nickel(II) form can be covalently grafted onto a platinum electrode by electrochemical reduction of the diazonium cation, generated in situ by a reaction of the nickel(II) aminoporphyrin with sodium nitrite and trifluoroacetic acid. The electrosynthesized thin film gives an electrochemical response typical of a porphyrin material. Films grown under…
Carbazole-based green and blue-BODIPY dyads and triads as donors for bulk heterojunction organic solar cells.
Two BODIPY derivatives with one (B2) and two (B3) carbazole moieties were synthesized and applied as electron-donor materials in organic photovoltaic cells (OPV). Their optical and electrochemical properties were systematically investigated. These BODIPY dyes exhibit excellent solubility in organic solvents and present high molar extinction coefficients (1.37–1.48 × 105 M−1 cm−1) in solutions with absorption maxima at 586 nm for mono-styryl groups and at 672 nm for di-styryl groups. The introduction of the styryl moieties results in a large bathochromic shift and a significant decrease in the HOMO–LUMO energy-gaps. The BODIPY dyes show relatively low HOMO energies ranging from −4.99 to −5.1…
Aminomethyl-Substituted Ferrocenes and Derivatives: Straightforward Synthetic Routes, Structural Characterization, and Electrochemical Analysis
A variety of aminomethyl-substituted ferrocenes and the parent compounds (iminomethyl)ferrocenes, azaferrocenophanes, and diferrocenylamines can be selectively synthesized from reductive amination of 1,1′-diformylferrocene or formylferrocene. The optimized one- or two-step reactions have delivered 13 new compounds, isolated in 65–97% yields, which include tertiary (ferrocenylmethyl)amines and azaferrocenophanes by using NaBH(OAc)3 as a mild reducing agent and (iminomethyl)ferrocenes and secondary (ferrocenylmethyl)amines by using LiAlH4. X-ray structures of representative members of these ferrocene derivative families have evidenced the preferred conformation adopted by ferrocene backbones,…
A general diastereoselective synthesis of highly functionalized ferrocenyl ambiphiles enabled on a large scale by electrochemical purification
International audience; A general synthesis of highly functionalized ferrocenes, which include (P,B)- and (N,B)-ambiphiles, has been developed at a multigram scale. Diastereoselective stepwise modification of di-tert-butylated ferrocenes included the unprecedented separation of electroactive species. Bulky alkyl groups on ferrocenes ensure planar chirality of ambiphiles and enforce closer proximity of antagonist Lewis functions.
Electrocatalytic properties of manganese and cobalt polyporphine films toward oxygen reduction reaction
International audience; Novel member of polymetalloporphines, namely manganese polymetalloporphine of type I (pMnP-I) obtained by ion exchange from magnesium polyporphine of type I (pMgP-I) is reported for the first time and compared to its cobalt analogue (pCoP-I). Both polymer films have been obtained via two-step procedure: demetaladon of the pMgP-I electrode film via its exposure to trifluoroacetic acid solution, resulting in formation of the metal-free polyporphine of type I (pH(2)P-I) followed by electrochemically induced incorporation of Co or Mn ions from the acetonitrile solution of cobalt and manganese perchlorates. A further oxidative transformation of pCoP-I, polymer films has l…
An electrochemical process to prepare and recycle biobased ionic liquids
This manuscript describes the first electrosynthesis of biobased ionic liquids from L-valine, oxalic acid and glyoxal, which is energy-efficient, does not emit toxic waste and avoids the formation of inorganic waste. These ionic liquids were then used in the development of our electro-recycling process. While their recycling yields are still moderated due to recombination and disproportionation reactions, this unprecedented recycling technology is very promising in terms of environmental and economic gains. Indeed, it has a high energy efficiency, requires low cost equipment, allows a strong decrease of the price of such ionic solvents, limits the use of non-renewable resources and solves t…
Crystallographic and (spectro)electrochemical characterizations of cobalt(II) 10-phenyl-5,15-di-p-tolylporphyrin
International audience; The synthesis, cyclic and rotating disk electrode voltammograms, UV-visible absorption and Xray diffraction analyses of cobalt(II) 10-phenyl-5,15-dip -tolylporphyrin (1-Co) are described. 1-Co was crystallized by slow diffusion of n-hexane into a concentrated CH2Cl2 solution. X-ray diffraction analyses reveals porphyrin aromatic cycle stacking in the crystal, C-H•••π interactions of the CH2Cl2 solvent with the π-system of one tolyl group and Co(II)•••π (porphyrin ring) interactions. The abstraction of 1.0 F/mol during the electrolysis at the first oxidation potential was followed by spectroelectrochemistry. It leads to the Co(II) → Co(III) transformation rather than …
In situ UV-visible spectroelectrochemistry in the course of oxidative monomer electrolysis
Abstract Novel method to characterize the macromolecuar structure of an electroactive polymer deposited via electrooxidation of the corresponding monomer on the electrode surface has been proposed. It is based on experimental determination of the number of electrons spent for oxidation of an initially solute monomer species which is used to calculate the number of covalent bonds linking each monomer unit with neighboring units inside the polymer. The former parameter is found by tracing simultaneously the variations of instantaneous values of the solute monomer concentration and of the passed charge in the course of the monomer oxidation electrolysis. This monomer concentration is establish…
Synthesis and structural characterisation of bulky heptaaromatic (hetero)aryl o-substituted s-aryltetrazines
An expedient two-step synthesis produces in good yield polyaromatic heptacyclic (hetero)arylated o-substituted s-aryltetrazines (s-Tz) directly from diphenyl s-tetrazine. This methodology overcomes the steric limitations of classical Pinner-like syntheses encountered for o-functionalized s-Tz. A single step palladium-catalyzed N-directed C–H bond tetrahalogenation is followed by a Pd-catalyzed Suzuki (hetero)arylation that is achieved simultaneously on four sites. The single crystal X-ray diffraction structure of the resulting typical polyaromatic heptacyclic aromatic compound 3,6-bis(2,6-diphenyl)-1,2,4,5-tetrazine (3) is analyzed, together with R-functionalized peripheral phenyl derivativ…
Oxidative C-N fusion of pyridinyl-substituted porphyrins.
International audience; The mild (electro) chemical oxidation of pyridin-2-ylthio-meso substituted Ni(II) porphyrins affords C-N fused cationic and dicationic pyridinium-based derivatives. These porphyrins are fully characterized and the molecular structure of one of them was confirmed by X-ray crystallography. A mechanism for the intramolecular oxidative C-N coupling is proposed based on theoretical calculations and cyclic voltammetry analyses.
Recent advances in electrochemical meso- and β-functionalization of porphyrins and electrografting of diazonium porphyrins
Abstract Recent studies on electrochemical meso- and β-functionalization of porphyrins and electrografting of diazonium porphyrin are presented. First, the electrochemical oxidative C–C coupling between porphyrins will be presented, followed by the intermolecular and intramolecular meso- and β-substitutions of porphyrins. Then, the latest results on diazonium porphyrin electrografting will be reviewed.
Long-range electronic connection in picket-fence like ferrocene–porphyrin derivatives
The effects of a direct connection between ferrocene and porphyrin units have been thoroughly investigated by electrochemical and spectroscopic methods. These data not only reveal that substitution of the porphyrin macrocycle by one, two, three or four ferrocenyl groups strongly affects the electronic properties of the porphyrin and ferrocenyl moieties, they also clearly demonstrate that the metallocene centres are "connected" through the porphyrin-based electronic network. The dynamic properties of selected ferrocene-porphyrin conjugates have been investigated by VT NMR and metadynamic calculations. 1,3-Dithiolanyl protecting groups have been introduced on the upper rings of the ferrocene …
ChemInform Abstract: Imidazolium and Potassium Hydrogen Carbonate Salts as Ecofriendly Organocatalysts for Oxazolidinone Synthesis.
Although oxazolidinones are valuable intermediate compounds for industrial applications, no synthetic method is suitable for their production on a large scale owing to the use of reagents/catalysts that are hazardous or toxic to human health or ecotoxic for the environment. In this manuscript, we describe new and efficient catalysts, that is, the nontoxic hydrogen carbonate anion in combination with a potassium or diisobutylimidazolium ([iBu(2)IM]) countercation, for the conversion of -amino alcohols into cyclic oxazolidinones in high yields of 69 to 90%. Depending on the catalytic conditions, both catalysts could be easily recovered from the crude reaction products and reused several times…
The Taming of Redox‐Labile Phosphidotitanocene Cations
International audience; Tame d0 phosphidotitanocene cations stabilized with a pendant tertiary phosphane arm are reported. These compounds were obtained by one-electron oxidation of d1 precursors with [Cp2Fe][BPh4]. The electronic structure of these compounds was studied experimentally (EPR, UV/Vis, and NMR spectroscopy, X-ray diffraction analysis) and through DFT calculations. The theoretical analysis of the bonding situation by using the electron localization function (ELF) shows the presence of π-interactions between the phosphido ligand and Ti in the d0 complexes, whereas dπ–pπ repulsion prevents such interactions in the d1 complexes. In addition, CH–π interactions were observed in seve…
Regioselective C–H amination of free base porphyrins via electrogenerated pyridinium-porphyrins and stabilization of easily oxidized amino-porphyrins by protonation
Four free base aminoporphyrins were synthesized in two steps via regioselective anodic nucleophilic substitution with pyridine followed by ring opening of the electrogenerated pyridinium with piperidine. The X-ray crystallographic structure of the unstable 2-aminotetraphenylporphyrin was solved. Protonation of this latter compound leads to the stable diiminium porphyrin salt.
Coordination Chemistry of a Bis(Tetrazine) Tweezer: A Case of Host-Guest Behavior with Silver Salts
The carbon-carbon cross-coupling of phenyl s-tetrazine (Tz) units at their ortho-phenyl positions allows the formation of constrained bis(tetrazines) with original tweezer structures. In these compounds, the face-to-face positioning of the central tetrazine cores is reinforced by π-stacking of the electron-poor nitrogen-containing heteroaromatic moieties. The resulting tetra-aromatic structure can be used as a weak coordinating ligand with cationic silver. This coordination generates a set of bis(tetrazine)-silver(I) coordination complexes tolerating a large variety of counter anions of various geometries, namely, PF6−, BF4−, SbF6−, ClO4−, NTf2−, and OTf−. These compounds were characterized…
Bio-based 1,3-diisobutyl imidazolium hydrogen oxalate [iBu 2 IM](HC 2 O 4 ) as CO 2 shuttle
International audience; This manuscript describes the using of biosourced L-valine, oxalic acid and glyoxal to produce a biobased imidazolium hydrogen oxalate [iBu(2)IM](HC2O4) which is converted to its related hydrogen carbonate salt by a simple electrolysis without using strong base. The addition of weak protic acids to the latter compound leads to a rapid and quantitative CO2 release with formation of the starting hydrogen oxalate salt or a new halide free bio-based ionic liquid [iBu(2)IM](AcO) which is able to adsorb reversibly the CO2 at room temperature. The protonation reactions, combined with electrolysis, could then be a promising alternative solution for storage and transport of C…
Ruthenium and Osmium Complexes of Phosphine-Porphyrin Derivatives as Potential Bimetallic Theranostics: Photophysical Studies
A series of (η6-p-cymene)ruthenium(II)- and osmium(II) complexes of porphyrin-phosphane derivatives have been synthesized as potential bimetallic theranostic candidates. The photophysical and electrochemical properties were investigated, and these species desirably exhibit no or almost no photoinduced intramolecular atom, energy, and electron transfer between the dye and the metallic fragment. These favorable features are mostly associated with the presence of their long chain (i.e., ∼ 1 nm) separating the two functional units. Interestingly, a decrease in emission intensity and lifetimes (up to 35-fold) has been observed, which was ascribed to a small heavy atom effect. This effect is poss…
Electrosynthesis as a powerful method for the generation of catalytic intermediates: efficient isolation of a palladium aryl halide oxidative addition product.
International audience; Polyphosphane ligands of controlled conformation promote highly efficient palladium-catalyzed cross-coupling reactions. Electrosynthesis has been used as a new straightforward method to obtain important intermediates in the search for a better mechanistic understanding. As a proof of concept, the facile synthesis of a phenyl iodopalladium(II) complex (2) was conducted at the electrolysis scale from a readily electrogenerated unstable Pd0 precursor.
Imidazolium and Potassium Hydrogen Carbonate Salts as Ecofriendly Organocatalysts for Oxazolidinone Synthesis
International audience; Although oxazolidinones are valuable intermediate compounds for industrial applications, no synthetic method is suitable for their production on a large scale owing to the use of reagents/catalysts that are hazardous or toxic to human health or ecotoxic for the environment. In this manuscript, we describe new and efficient catalysts, that is, the nontoxic hydrogen carbonate anion in combination with a potassium or diisobutylimidazolium ([iBu(2)IM]) countercation, for the conversion of -amino alcohols into cyclic oxazolidinones in high yields of 69 to 90%. Depending on the catalytic conditions, both catalysts could be easily recovered from the crude reaction products …
Bridge-Clamp Bis(tetrazine)s with [N] 8 π-Stacking Interactions and Azido- s -Aryl Tetrazines: Two Classes of Doubly Clickable Tetrazines
Click chemistry at a tetrazine core is useful for bioorthogonal labeling and crosslinking. Introduced here are two new classes of doubly clickable s-aryl tetrazines synthesized by Cu-catalyzed cross-coupling. Homocoupling of o-brominated s-aryl tetrazines leads to bis(tetrazine)s structurally characterized by tetrazine cores arranged face-to-face. [N]8 π-stacking interactions are essential to the conformation. Upon inverse electron demand Diels-Alder (iEDDA) cycloaddition, the bis(tetrazine)s produce a unique staple structure. The o-azidation of s-aryl tetrazines introduces a second proximal intermolecular clickable function that leads to double click chemistry opportunities. The stepwise i…
Electrochemical meso-functionalization of magnesium(II) porphine
International audience; Regioselective meso-functionalization of the totally unsubstituted magnesium(II) porphine was performed by controlled potential electrolysis with pyridine and triphenylphosphine as nucleophiles leading to the original pyridinium and phosphonium substituted derivatives, respectively. The crystallographic structure of the latter is described as the only meso-phosphonium porphyrin reported to date.
Reappraising Schmidpeter's bis(iminophosphoranyl)phosphides: coordination to transition metals and bonding analysis
The synthesis and characterization of a range of bis(iminophosphoranyl)phosphide (BIPP) group 4 and coinage metals complexes is reported. BIPP ligands bind group 4 metals in a pseudo fac-fashion, and the central phosphorus atom enables the formation of d0–d10 heterobimetallic complexes. Various DFT computational tools (including AIM, ELF and NCI) show that the phosphorus–metal interaction is either electrostatic (Ti) or dative (Au, Cu). A bridged homobimetallic Cu–Cu complex was also prepared and its spectroscopic properties were investigated. The theoretical analysis of the P–P bond in BIPP complexes reveals that (i) BIPP are closely related to ambiphilic triphosphenium (TP) cations; (ii) …
CCDC 1983790: Experimental Crystal Structure Determination
Related Article: Tuan‐Anh Nguyen, Julien Roger, Houssein Nasrallah, Vincent Rampazzi, Sophie Fournier, Hélène Cattey, E. Daiann Sosa Carrizo, Paul Fleurat‐Lessard, Charles H. Devillers, Nadine Pirio, Dominique Lucas, Jean‐Cyrille Hierso|2020|Chem.Asian J.|15|2879|doi:10.1002/asia.202000579
CCDC 1532854: Experimental Crystal Structure Determination
Related Article: Emmanuel Lerayer, Patrice Renaut, Julien Roger, Nadine Pirio, Hélène Cattey, Charles H. Devillers, Dominique Lucas, Jean-Cyrille Hierso|2017|Chem.Commun.|53|6017|doi:10.1039/C7CC02469J
CCDC 1871410: Experimental Crystal Structure Determination
Related Article: Adrien T. Normand, Quentin Bonnin, Stéphane Brandès, Philippe Richard, Paul Fleurat-Lessard, Charles H. Devillers, Cédric Balan, Pierre Le Gendre, Gerald Kehr, Gerhard Erker|2019|Chem.-Eur.J.|25|2803|doi:10.1002/chem.201805430
CCDC 1828692: Experimental Crystal Structure Determination
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CCDC 1871415: Experimental Crystal Structure Determination
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CCDC 1871416: Experimental Crystal Structure Determination
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CCDC 1871408: Experimental Crystal Structure Determination
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CCDC 1908608: Experimental Crystal Structure Determination
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CCDC 1908609: Experimental Crystal Structure Determination
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CCDC 939068: Experimental Crystal Structure Determination
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CCDC 1919134: Experimental Crystal Structure Determination
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CCDC 2006293: Experimental Crystal Structure Determination
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CCDC 1919135: Experimental Crystal Structure Determination
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CCDC 1532860: Experimental Crystal Structure Determination
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CCDC 980179: Experimental Crystal Structure Determination
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CCDC 980175: Experimental Crystal Structure Determination
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CCDC 1828690: Experimental Crystal Structure Determination
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CCDC 1557313: Experimental Crystal Structure Determination
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CCDC 1848218: Experimental Crystal Structure Determination
Related Article: Abdou K. D. Dimé, Hélène Cattey, Dominique Lucas, Charles H. Devillers|2018|Eur.J.Org.Chem.|2018|4834|doi:10.1002/ejic.201801142
CCDC 1985146: Experimental Crystal Structure Determination
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CCDC 1985142: Experimental Crystal Structure Determination
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CCDC 1983787: Experimental Crystal Structure Determination
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CCDC 981913: Experimental Crystal Structure Determination
Related Article: Abdou K. D. Dimé, Charles H. Devillers, Hélène Cattey, Dominique Lucas|2014|Dalton Trans.|43|14554|doi:10.1039/C4DT00221K
CCDC 1985138: Experimental Crystal Structure Determination
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CCDC 1532862: Experimental Crystal Structure Determination
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CCDC 1985136: Experimental Crystal Structure Determination
Related Article: Adrien T. Normand, E. Daiann Sosa Carrizo, Corentin Magnoux, Esteban Lobato, Hélène Cattey, Philippe Richard, Stéphane Brandès, Charles H. Devillers, Anthony Romieu, Pierre Le Gendre, Paul Fleurat-Lessard|2021|Chemical Science|12|253|doi:10.1039/D0SC04736H
CCDC 1993888: Experimental Crystal Structure Determination
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CCDC 1908612: Experimental Crystal Structure Determination
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CCDC 1991440: Experimental Crystal Structure Determination
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CCDC 980177: Experimental Crystal Structure Determination
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CCDC 1871418: Experimental Crystal Structure Determination
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CCDC 1983797: Experimental Crystal Structure Determination
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CCDC 1532856: Experimental Crystal Structure Determination
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CCDC 939067: Experimental Crystal Structure Determination
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CCDC 1871412: Experimental Crystal Structure Determination
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CCDC 1828691: Experimental Crystal Structure Determination
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CCDC 1871414: Experimental Crystal Structure Determination
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CCDC 980178: Experimental Crystal Structure Determination
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CCDC 1983798: Experimental Crystal Structure Determination
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CCDC 1532855: Experimental Crystal Structure Determination
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CCDC 1559130: Experimental Crystal Structure Determination
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CCDC 1952439: Experimental Crystal Structure Determination
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CCDC 1908611: Experimental Crystal Structure Determination
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CCDC 1983791: Experimental Crystal Structure Determination
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CCDC 1985140: Experimental Crystal Structure Determination
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CCDC 980174: Experimental Crystal Structure Determination
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CCDC 1908610: Experimental Crystal Structure Determination
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CCDC 980176: Experimental Crystal Structure Determination
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CCDC 1908606: Experimental Crystal Structure Determination
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CCDC 1983795: Experimental Crystal Structure Determination
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CCDC 1985143: Experimental Crystal Structure Determination
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CCDC 1871411: Experimental Crystal Structure Determination
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CCDC 1908607: Experimental Crystal Structure Determination
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CCDC 1828689: Experimental Crystal Structure Determination
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CCDC 1871409: Experimental Crystal Structure Determination
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CCDC 981911: Experimental Crystal Structure Determination
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CCDC 1532861: Experimental Crystal Structure Determination
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CCDC 981912: Experimental Crystal Structure Determination
Related Article: Abdou K. D. Dimé, Charles H. Devillers, Hélène Cattey, Dominique Lucas|2014|Dalton Trans.|43|14554|doi:10.1039/C4DT00221K
CCDC 1559132: Experimental Crystal Structure Determination
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CCDC 1983789: Experimental Crystal Structure Determination
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CCDC 1848217: Experimental Crystal Structure Determination
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CCDC 1871417: Experimental Crystal Structure Determination
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CCDC 1532859: Experimental Crystal Structure Determination
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CCDC 981910: Experimental Crystal Structure Determination
Related Article: Abdou K. D. Dimé, Charles H. Devillers, Hélène Cattey, Dominique Lucas|2014|Dalton Trans.|43|14554|doi:10.1039/C4DT00221K
CCDC 1557314: Experimental Crystal Structure Determination
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CCDC 1985135: Experimental Crystal Structure Determination
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CCDC 1985137: Experimental Crystal Structure Determination
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CCDC 1985139: Experimental Crystal Structure Determination
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CCDC 1910052: Experimental Crystal Structure Determination
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CCDC 1016993: Experimental Crystal Structure Determination
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CCDC 1035220: Experimental Crystal Structure Determination
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CCDC 1559131: Experimental Crystal Structure Determination
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CCDC 980180: Experimental Crystal Structure Determination
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CCDC 1983788: Experimental Crystal Structure Determination
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CCDC 1983796: Experimental Crystal Structure Determination
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CCDC 1016994: Experimental Crystal Structure Determination
Related Article: Charles H. Devillers, Seydou Hebié, Dominique Lucas, Hélène Cattey, Sébastien Clément, and Sébastien Richeter|2014|J.Org.Chem.|79|6424|doi:10.1021/jo5005586
CCDC 1985134: Experimental Crystal Structure Determination
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CCDC 1813003: Experimental Crystal Structure Determination
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CCDC 1532857: Experimental Crystal Structure Determination
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CCDC 1983794: Experimental Crystal Structure Determination
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CCDC 1952440: Experimental Crystal Structure Determination
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CCDC 1983793: Experimental Crystal Structure Determination
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CCDC 1985141: Experimental Crystal Structure Determination
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