0000000001298826
AUTHOR
Sergey E. Nefedov
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 …
Synthesis of (trans-A2)BC-Type Porphyrins with Acceptor Diethoxyphosphoryl and Various Donor Groups and their Assembling in the Solid State and at Interfaces
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…
Synthesis and Self-Organization of Zinc β-(Dialkoxyphosphoryl)porphyrins in the Solid State and in Solution
The first synthesis and self-organization of zinc β-phosphorylporphyrins in the solid state and in solution are reported. β-Dialkoxyphosphoryl-5,10,15,20-tetraphenylporphyrins and their Zn(II) complexes have been synthesized in good yields by using Pd- and Cu-mediated carbon-phosphorous bond-forming reactions. The Cu-mediated reaction allowed to prepare the mono-β-(dialkoxyphosphoryl)porphyrins 1 Zn-3 Zn starting from the β-bromo-substituted zinc porphyrinate ZnTPPBr (TPP = tetraphenylporphyrin) and dialkyl phosphites HP(O)(OR)(2) (R = Et, iPr, nBu). The derivatives 1 Zn-3 Zn were obtained in good yields by using one to three equivalents of CuI. When the reaction was carried out in the pres…
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].
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.
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…
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…
CCDC 902786: Experimental Crystal Structure Determination
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CCDC 960835: Experimental Crystal Structure Determination
Related Article: Alexander Yu. Mitrofanov, Yoann Rousselin, Roger Guilard, Stéphane Brandès, Alla G. Bessmertnykh-Lemeune, Marina A. Uvarova, Sergey E. Nefedov|2016|New J.Chem.|40|5896|doi:10.1039/C5NJ03572D
CCDC 1017124: Experimental Crystal Structure Determination
Related Article: Marina A. Uvarova, Anna A. Sinelshchikova, Margarita A. Golubnichaya, Sergey E. Nefedov, Yulia Yu. Enakieva, Yulia G. Gorbunova, Aslan Yu. Tsivadze, Christine Stern, Alla Bessmertnykh-Lemeune, Roger Guilard|2014|Cryst.Growth Des.|14|5976|doi:10.1021/cg501157e
CCDC 1049575: Experimental Crystal Structure Determination
Related Article: Alexander Yu. Mitrofanov, Yoann Rousselin, Roger Guilard, Stéphane Brandès, Alla G. Bessmertnykh-Lemeune, Marina A. Uvarova, Sergey E. Nefedov|2016|New J.Chem.|40|5896|doi:10.1039/C5NJ03572D
CCDC 1519796: Experimental Crystal Structure Determination
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CCDC 902785: Experimental Crystal Structure Determination
Related Article: Anna A. Sinelshchikova, Sergey E. Nefedov, Yulia Yu. Enakieva, Yulia G. Gorbunova, Aslan Yu. Tsivadze, Karl M. Kadish, Ping Chen, Alla Bessmertnykh-Lemeune, Christine Stern, and Roger Guilard|2013|Inorg.Chem.|52|999|doi:10.1021/ic302257g
CCDC 1844989: Experimental Crystal Structure Determination
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CCDC 1017131: Experimental Crystal Structure Determination
Related Article: Marina A. Uvarova, Anna A. Sinelshchikova, Margarita A. Golubnichaya, Sergey E. Nefedov, Yulia Yu. Enakieva, Yulia G. Gorbunova, Aslan Yu. Tsivadze, Christine Stern, Alla Bessmertnykh-Lemeune, Roger Guilard|2014|Cryst.Growth Des.|14|5976|doi:10.1021/cg501157e
CCDC 1844993: Experimental Crystal Structure Determination
Related Article: Sergey E. Nefedov, Kirill P. Birin, Alla Bessmertnykh-Lemeune, Yulia Y. Enakieva, Anna A. Sinelshchikova, Yulia G. Gorbunova, Aslan Y. Tsivadze, Christine Stern, Yuanyuan Fang, Karl M. Kadish|2019|Dalton Trans.|48|5372|doi:10.1039/C9DT00706G
CCDC 1017125: Experimental Crystal Structure Determination
Related Article: Marina A. Uvarova, Anna A. Sinelshchikova, Margarita A. Golubnichaya, Sergey E. Nefedov, Yulia Yu. Enakieva, Yulia G. Gorbunova, Aslan Yu. Tsivadze, Christine Stern, Alla Bessmertnykh-Lemeune, Roger Guilard|2014|Cryst.Growth Des.|14|5976|doi:10.1021/cg501157e
CCDC 998788: Experimental Crystal Structure Determination
Related Article: Roman I. Zubatyuk, Anna A. Sinelshchikova, Yulia Y. Enakieva, Yulia G. Gorbunova, Aslan Y. Tsivadze, Sergey E. Nefedov, Alla Bessmertnykh-Lemeune, Roger Guilard, Oleg V. Shishkin|2014|CrystEngComm|16|10428|doi:10.1039/C4CE01623H
CCDC 1519795: Experimental Crystal Structure Determination
Related Article: Yulia Yu. Enakieva, Marina V. Volostnykh, Sergey E. Nefedov, Gayane A. Kirakosyan, Yulia G. Gorbunova, Aslan Yu. Tsivadze, Alla G. Bessmertnykh-Lemeune, Christine Stern, Roger Guilard|2017|Inorg.Chem.|56|3055|doi:10.1021/acs.inorgchem.6b03160
CCDC 1890813: Experimental Crystal Structure Determination
Related Article: Yuanyuan Fang, Xiaoqin Jiang, Karl M. Kadish, Sergey E. Nefedov, Gayane A. Kirakosyan, Yulia Y. Enakieva, Yulia G. Gorbunova, Aslan Y. Tsivadze, Christine Stern, Alla Bessmertnykh-Lemeune, Roger Guilard|2019|Inorg.Chem.|58|4665|doi:10.1021/acs.inorgchem.9b00268
CCDC 1017126: Experimental Crystal Structure Determination
Related Article: Marina A. Uvarova, Anna A. Sinelshchikova, Margarita A. Golubnichaya, Sergey E. Nefedov, Yulia Yu. Enakieva, Yulia G. Gorbunova, Aslan Yu. Tsivadze, Christine Stern, Alla Bessmertnykh-Lemeune, Roger Guilard|2014|Cryst.Growth Des.|14|5976|doi:10.1021/cg501157e
CCDC 1009948: Experimental Crystal Structure Determination
Related Article: Alexander Yu. Mitrofanov, Yoann Rousselin, Roger Guilard, Stéphane Brandès, Alla G. Bessmertnykh-Lemeune, Marina A. Uvarova, Sergey E. Nefedov|2016|New J.Chem.|40|5896|doi:10.1039/C5NJ03572D
CCDC 1893716: Experimental Crystal Structure Determination
Related Article: Elizaveta V. Ermakova, Yulia Y. Enakieva, Sergey E. Nefedov, Vladimir V. Arslanov, Yulia G. Gorbunova, Aslan Y. Tsivadze, Christine Stern, Alla Lemeune|2019|Eur.J.Org.Chem.|2019|3146|doi:10.1002/ejoc.201900448
CCDC 1017127: Experimental Crystal Structure Determination
Related Article: Marina A. Uvarova, Anna A. Sinelshchikova, Margarita A. Golubnichaya, Sergey E. Nefedov, Yulia Yu. Enakieva, Yulia G. Gorbunova, Aslan Yu. Tsivadze, Christine Stern, Alla Bessmertnykh-Lemeune, Roger Guilard|2014|Cryst.Growth Des.|14|5976|doi:10.1021/cg501157e
CCDC 1844991: Experimental Crystal Structure Determination
Related Article: Sergey E. Nefedov, Kirill P. Birin, Alla Bessmertnykh-Lemeune, Yulia Y. Enakieva, Anna A. Sinelshchikova, Yulia G. Gorbunova, Aslan Y. Tsivadze, Christine Stern, Yuanyuan Fang, Karl M. Kadish|2019|Dalton Trans.|48|5372|doi:10.1039/C9DT00706G
CCDC 1017128: Experimental Crystal Structure Determination
Related Article: Marina A. Uvarova, Anna A. Sinelshchikova, Margarita A. Golubnichaya, Sergey E. Nefedov, Yulia Yu. Enakieva, Yulia G. Gorbunova, Aslan Yu. Tsivadze, Christine Stern, Alla Bessmertnykh-Lemeune, Roger Guilard|2014|Cryst.Growth Des.|14|5976|doi:10.1021/cg501157e
CCDC 1017130: Experimental Crystal Structure Determination
Related Article: Marina A. Uvarova, Anna A. Sinelshchikova, Margarita A. Golubnichaya, Sergey E. Nefedov, Yulia Yu. Enakieva, Yulia G. Gorbunova, Aslan Yu. Tsivadze, Christine Stern, Alla Bessmertnykh-Lemeune, Roger Guilard|2014|Cryst.Growth Des.|14|5976|doi:10.1021/cg501157e
CCDC 902787: Experimental Crystal Structure Determination
Related Article: Anna A. Sinelshchikova, Sergey E. Nefedov, Yulia Yu. Enakieva, Yulia G. Gorbunova, Aslan Yu. Tsivadze, Karl M. Kadish, Ping Chen, Alla Bessmertnykh-Lemeune, Christine Stern, and Roger Guilard|2013|Inorg.Chem.|52|999|doi:10.1021/ic302257g
CCDC 1519797: Experimental Crystal Structure Determination
Related Article: Yulia Yu. Enakieva, Marina V. Volostnykh, Sergey E. Nefedov, Gayane A. Kirakosyan, Yulia G. Gorbunova, Aslan Yu. Tsivadze, Alla G. Bessmertnykh-Lemeune, Christine Stern, Roger Guilard|2017|Inorg.Chem.|56|3055|doi:10.1021/acs.inorgchem.6b03160
CCDC 960834: Experimental Crystal Structure Determination
Related Article: Alexander Yu. Mitrofanov, Yoann Rousselin, Roger Guilard, Stéphane Brandès, Alla G. Bessmertnykh-Lemeune, Marina A. Uvarova, Sergey E. Nefedov|2016|New J.Chem.|40|5896|doi:10.1039/C5NJ03572D
CCDC 1844992: Experimental Crystal Structure Determination
Related Article: Sergey E. Nefedov, Kirill P. Birin, Alla Bessmertnykh-Lemeune, Yulia Y. Enakieva, Anna A. Sinelshchikova, Yulia G. Gorbunova, Aslan Y. Tsivadze, Christine Stern, Yuanyuan Fang, Karl M. Kadish|2019|Dalton Trans.|48|5372|doi:10.1039/C9DT00706G
CCDC 1844990: Experimental Crystal Structure Determination
Related Article: Sergey E. Nefedov, Kirill P. Birin, Alla Bessmertnykh-Lemeune, Yulia Y. Enakieva, Anna A. Sinelshchikova, Yulia G. Gorbunova, Aslan Y. Tsivadze, Christine Stern, Yuanyuan Fang, Karl M. Kadish|2019|Dalton Trans.|48|5372|doi:10.1039/C9DT00706G
CCDC 1519794: Experimental Crystal Structure Determination
Related Article: Yulia Yu. Enakieva, Marina V. Volostnykh, Sergey E. Nefedov, Gayane A. Kirakosyan, Yulia G. Gorbunova, Aslan Yu. Tsivadze, Alla G. Bessmertnykh-Lemeune, Christine Stern, Roger Guilard|2017|Inorg.Chem.|56|3055|doi:10.1021/acs.inorgchem.6b03160
CCDC 1009991: Experimental Crystal Structure Determination
Related Article: Alexander Yu. Mitrofanov, Yoann Rousselin, Roger Guilard, Stéphane Brandès, Alla G. Bessmertnykh-Lemeune, Marina A. Uvarova, Sergey E. Nefedov|2016|New J.Chem.|40|5896|doi:10.1039/C5NJ03572D
CCDC 998789: Experimental Crystal Structure Determination
Related Article: Roman I. Zubatyuk, Anna A. Sinelshchikova, Yulia Y. Enakieva, Yulia G. Gorbunova, Aslan Y. Tsivadze, Sergey E. Nefedov, Alla Bessmertnykh-Lemeune, Roger Guilard, Oleg V. Shishkin|2014|CrystEngComm|16|10428|doi:10.1039/C4CE01623H
CCDC 998787: Experimental Crystal Structure Determination
Related Article: Roman I. Zubatyuk, Anna A. Sinelshchikova, Yulia Y. Enakieva, Yulia G. Gorbunova, Aslan Y. Tsivadze, Sergey E. Nefedov, Alla Bessmertnykh-Lemeune, Roger Guilard, Oleg V. Shishkin|2014|CrystEngComm|16|10428|doi:10.1039/C4CE01623H
CCDC 998790: Experimental Crystal Structure Determination
Related Article: Roman I. Zubatyuk, Anna A. Sinelshchikova, Yulia Y. Enakieva, Yulia G. Gorbunova, Aslan Y. Tsivadze, Sergey E. Nefedov, Alla Bessmertnykh-Lemeune, Roger Guilard, Oleg V. Shishkin|2014|CrystEngComm|16|10428|doi:10.1039/C4CE01623H