650598-88-2Relevant academic research and scientific papers
Synthesis, spectral and electrochemical redox properties of N-methyl fused nickel(II) porphyrin
Ahmad Dar, Tawseef,Mandeep,Sankar, Muniappan
, p. 1106 - 1110 (2019/01/03)
N-methyl fused nickel(II) porphyrin was synthesized by a facile synthetic route in excellent yield. The effect of the electron-donating methyl group on spectral and electrochemical redox properties was analyzed by comparing the electrochemistry with that of its precursors. N-methylated fused nickel(II) porphyrin exhibited a red-shifted absorption spectrum (δλmax = 6-13 nm) and a 180mV anodic shift in the first ring oxidation as well as a 210mV shift in reduction with respect to its Ni(II)-fused porphyrin precursor (NiII-(NH)TPP). However, the absorption spectral features and redox potentials of N-methyl fused nickel(II) porphyrin are marginally shifted as compared to its immediate precursor, β-formyl Ni(II)-fused porphyrin. Notably, Ni(II)(N-CH3)(CHO)TPP exhibited a third oxidation at 1.51mV, corresponding to oxidation of Ni(II) to Ni(III) due to the presence of push-pull β substituents.
Expanding the light absorption of poly(3-hexylthiophene) by end-functionalization with π-extended porphyrins
Chevrier, Michèle,Richeter, Sébastien,Coulembier, Olivier,Surin, Mathieu,Mehdi, Ahmad,Lazzaroni, Roberto,Evans, Rachel C.,Dubois, Philippe,Clément, Sébastien
, p. 171 - 174 (2015/12/26)
Poly(3-hexylthiophene)s end-functionalized with π-extended porphyrins have been synthesized in a one-pot procedure. The polymers show a broad absorption profile extending to 700 nm and a fibrillar microstructure, which can be tuned through judicious selection of the porphyrin molar ratio.
A porphyrin with two coordination sites: The biquinoline ligand as a new potential external chelate
Jeandon, Christophe,Ruppert, Romain
scheme or table, p. 4098 - 4102 (2011/09/14)
A highly symmetrical doubly fused porphyrin was obtained after two successive intramolecular cyclizations.1 The first supplementary ring was closed by using the Cadogan reaction, involving the generation of an intermediate nitrene from the starting nitro
A new approach to N-phenylquinolino[2,3,4-at]porphyrins: Electrochemical and photochemical studies
Pereira, Ana M.V.M.,Neves, Maria G.P.M.S,Cavaleiro, José A.S.,Gisselbrecht, Jean-Paul,Jeandon, Christophe,Ruppert, Romain
scheme or table, p. 575 - 582 (2012/05/05)
A new route to N-phenylquinolino[2,3,4-at]porphyrins is described and the electrochemical and photochemical properties of the synthesized derivatives were investigated. The electrochemical studies (cyclic voltammetry and rotating disk voltammetry) of the
Synthesis, characterization, and electrochemical studies of new π-Extended metalloporphyrins
Jimenez, Angel J.,Jeandon, Christophe,Gisselbrecht, Jean-Paul,Ruppert, Romain
experimental part, p. 5725 - 5730 (2010/03/01)
A doubly fused porphyrin has been synthesized by two successive cyclization reactions. The first meso-phenyl group was fused, by an intramolecular Cadogan reaction leading to an enamine-functionalized porphyrin. After Vilsmeier-Haack formylation of the ni
Synthesis of New Porphyrins with Peripheral Conjugated Chelates and Their Use for the Preparation of Porphyrin Dimers Linked by Metal Ions
Richeter, Sebastien,Jeandon, Christophe,Gisselbrecht, Jean-Paul,Graff, Roland,Ruppert, Romain,Callot, Henry J.
, p. 251 - 263 (2008/10/09)
This article describes the preparation of several new porphyrins bearing chelating peripheral groups fully conjugated with the macrocyclic π-system. Treatment of a 2-nitro-meso-tetraarylporphydn with phosphite gave a cyclic enamine, whose formylation gave an enaminoaldehyde. The thio analogue was obtained on treatment with Lawesson's reagent. The same reagent was also used to obtain the isomeric thioenaminoketone chelates. A enaminoketone ligand was prepared from a porphyrinic pyrrolone. All these ligands, as internal nickel complexes, could be metalated with palladium to yield porphyrinic dimers. The dimers obtained from enaminoketones and thioketones show a trans geometry, while in the enaminoaldehyde and -thioaldehyde series the cis isomer is thermodynamically favored. The bathochromic shifts of the electronic spectra of the aldehyde-derived dimers illustrate the strong electronic effect of peripheral metalation and dimerization. However, in the case of the pyrrolone-derived ligand, opposite effects were observed, due to partial reconstitution of the porphyrin chromophore on complexation. As with the dimers derived from enaminoketones, the dimers derived from the new ligands show typical splitting (up to 190 mV) of the electrochemical waves confirming large porphyrin-porphyrin interactions.
