131507-72-7Relevant articles and documents
The synthesis and solution conformation of dodecaphenylporphyrin
Medforth, Craig J.,Smith, Jevin J.
, p. 5583 - 5586 (1990)
The synthesis of 2,3 ,5 ,7 ,8 ,10 ,12 ,13 ,15 ,17, 18,20-dodecaphenylporphyrin (DPP ; 3) is reported; compared with similar porphyrins it shows a red. shifted electronic absorption spectrum, indicating a non-planar conformation in solution. Variable temperature 500 MHz NMR experiments give a ΔG* of 10.9 kcal mol-1 at 253 K for inversion of the macrocycle.
Effect of ligand nonplanarity and solvent nature on the kinetic stability of zinc porphyrin complexes
Berezin,Shukhto,Shatunov
, p. 997 - 1004 (2008)
Planarity disturbance in metal porphyrin macrorings produces destabilization of complexes in dimethyl sulfoxide-acetic acid and benzene-acetic acid systems, except for cases where the coordination center is additionally stabilized by endocyclic substituents and/or extra ligands. The first dissociation stage of complexes with N-substituted analogs of porphyrins involves substitution of the acido ligand in the strongly shielded coordination sphere by an electron-donor solvent molecule. The revealed dependences of dissociation rate constants on acid concentration in DMSO, untypical of most metal porphyrins, are explained by a change in the type of the attacking species with changing solvent composition. The dissociation rate constants of complexes in an electron donor solvent can be lower by several orders of magnitude than in a weakly solvating medium.
Novel dodecaarylporphyrins: Synthesis and dynamic properties
Muzzi, Cinzia M.,Medforth, Craig J.,Voss, Lisa,Cancilla, Mark,Lebrilla, Carlito,Ma, Jian-Guo,Shelnutt, John A.,Smith, Kevin M.
, p. 6159 - 6162 (1999)
An investigation of the synthesis of dodecaarylporphyrins using the Suzuki coupling reaction of arylboronic acids with octabromotetraarylporphyrins is reported. Variable temperature 1H NMR studies of these new porphyrins reveal several dynamic processes including the first examples of β-aryl rotation.
Synthesis of beta-aryl substituted porphyrins by palladium catalyzed Suzuki cross-coupling reactions
Chan, Kin Shing,Zhou, Xiang,Au, Ming Tak,Tam, Chak Yue
, p. 3129 - 3136 (1995)
β-Bromoporphyrins undergo Suzuki cross coupling reactions with aryl boronic to give β-arylporphyrins in high yields.
Saddle-shaped dioxo-ruthenium(VI) and -osmium(VI) 2,3,5,7,8,10,12,13,15,17,18,20-dodecaphenylporphyrin (H2dpp) complexes. Synthesis, spectral characterisation and alkene oxidation by [RuVI(dpp)O2]
Liu, Chun-Jing,Yu, Wing-Yiu,Peng, Shie-Ming,Mak, Thomas C. W.,Che, Chi-Ming
, p. 1805 - 1812 (2007/10/03)
An improved procedure for the preparation of the saddle-distorted porphyrin 2,3,5,7,8,10,12,13,15,17,18,20-dodecaphenylporphyrin (H2dpp) (yield = 75%) based on the Suzuki cross-coupling reaction between phenylboronic acid PhB(OH)2 an
Synthesis of 3,4-diarylpyrroles and conversion into dodecaarylporphyrins; a new approach to porphyrins with altered redox potentials
Ono, Noboru,Miyagawa, Hirokazu,Ueta, Takahiro,Ogawa, Takuji,Tani, Hiroyuki
, p. 1595 - 1601 (2007/10/03)
3,4-Diarylpyrroles (1) have been directly prepared in 20-50% yield by the reaction of β-nitrostyrenes with aqueous TiCl3 in 1,4-dioxane. Pyrroles 1 were also prepared via Barton-Zard pyrrole synthesis using the reaction of α-nitrostilbenes with ethyl isocyanoacetate followed by de-ethoxycarbonylation. 3,4-Diarylpyrroles have been converted into dodecaarylporphyrins by reaction with aromatic aldehydes. Various aryl groups are readily introduced at the periphery of porphyrins by this method. Phenyl substitution at any of the positions of pyrroles decreases E1/2ox while E1/2red is almost unchanged. On the other hand, substitution of the 2-thienyl group affects both the HOMO and LUMO energies, and the UV-vis spectra of dodeca-2-thienylporphyrins (4f or 4i) are extremely red-shifted.
