80529-82-4Relevant academic research and scientific papers
A new synthesis of benzoporphyrins using 4,7-dihydro-4,7-ethano-2H-isoindole as a synthon of isoindole
Ito, Satoshi,Murashima, Takashi,Uno, Hidemitsu,Ono, Noboru
, p. 1661 - 1662 (1998)
Heating 4,7-dihydro-4,7-ethano-2H-isoindole at 200 °C induces the retro-Diels-Alder reaction to give isoindole in essentially quantitative yield, which can be applied to a new synthesis of tetrabenzoporphyrins and monobenzoporphyrins.
Electrochemistry of zinc tetraarylporphyrins containing fused butano and benzo groups. Effect of solvent and substituents on spectra, potentials and mechanism in nonaqueous media
Ye, Lina,Fang, Yuanyuan,Ou, Zhongping,Wang, Liping,Xue, Songlin,Sun, Jing,Kadish, Karl M.
, p. 1129 - 1142 (2018)
Two series of zinc tetraarylporphyrins containing four β,β′-pyrrole fused butano or benzo groups were synthesized and characterized as to their electrochemical and spectroelectrochemical properties in nonaqueous media. The examined compounds are represented as butano(Ar)4PorZn and benzo(Ar)4PorZn, where Por is the porphyrin dianion and Ar is a p-CH3Ph, Ph or p-ClPh substitutent on meso-positions of the macrocycle. Each Zn(II) butano-And benzoporphyrin undergoes two one-electron reductions to give a p-Anion radical and dianion in CH2Cl2. In contrast, three reductions were observed for the benzoporphyrin derivatives in pyridine, the third of which is assigned as electron addition to a benzophlorin anion generated from the doubly reduced benzoporphyrin. Two overlapped one-electron oxidations were observed for the butanoporphyrins in CH2Cl2, a result not previously observed for any other zinc porphyrin. The electrochemically measured HOMO-LUMO gap of the benzoporphyrins ranges from 1.89 to 1.90 V in CH2Cl2 and from 1.93 to 1.95 V in pyridine. Both values are smaller than the gaps of butanoporphyrins at 2.11-2.13 V in CH2Cl2 and 2.07.2.09 V in pyridine.
Axial coordination reactions with nitrogenous bases and determination of equilibrium constants for zinc tetraarylporphyrins containing four β, β ′-fused butano and benzo groups in nonaqueous media
Ye, Lina,Fang, Yuanyuan,Ou, Zhongping,Wang, Liping,Xue, Songlin,Lu, Yang,Kadish, Karl M.
, p. 196 - 206 (2019/02/19)
The axial coordination properties of six zinc tetraarylporphyrins with seven different nitrogenous bases were examined in CH2Cl2 for derivatives containing four β,β′-fused butano or benzo groups and the equilibrium constants (logK) determined using spectral titration methods. The examined compounds are represented as butano(YPh)4PorZn and benzo(YPh)4PorZn, where Por is the porphyrin dianion and Y is a CH3, H or Cl substituent on the para-position of each meso-phenyl ring of the macrocycle. The initial four-coordinate butano-And benzoporphyrins will axially bind one nitrogenous base to form five-coordinate derivatives in CH2Cl2 and this leads to a 4-22 nm red-shift of the Soret and Q bands. The logK values range from 1.98 to 4.69 for butano(YPh)4PorZn and from 3.42 to 5.36 for benzo(YPh)4PorZn, with the exact value depending upon the meso and β-substituents of the porphyrin and the conjugate acid dissociation constants (pKa) of the nitrogenous base.
Zinc(ii) tetraphenyltetrabenzoporphyrin complex as triplet photosensitizer for triplet-triplet annihilation upconversion
Cui, Xiaoneng,Zhao, Jianzhang,Yang, Pei,Sun, Jifu
supporting information, p. 10221 - 10223 (2013/10/22)
Zn(ii) tetraphenyltetrabenzoporphyrin (TPTBP) and the free base H 2TPTBP were used as triplet photosensitizers for triplet-triplet annihilation (TTA) upconversion, to replace the long-established precious metal complex triplet photosensitizers such as those containing Pd(ii)-Pt(ii) atoms.
Metal exchange reactions in cadmium complexes with porphyrins of various structures
Berezin,Shukhto,Reshetyan
, p. 518 - 526 (2010/08/04)
The reaction kinetics of the metal exchange Cd(II)-Cu(II) and Cd(II)-Zn(II) in the cadmium complexes (CdP) with porphyrin ligands (H2P) differing by degree of stiffness (tetraphenylporphin, N- methyltetraphenylporphin, and tetraphenyltetrabenzoporphin) in the DMSO medium, was studied using spectrophotometric method. The rate of metal exchange reaction depends on the nature of the non-planatrity of H2P in the structure of CdP complexes, as well as on the additional screening of the reaction center MN4 by the extra-ligands and substituents. The reduction of the coordinating ability of the anion X- in the structure of the solvate-salt of incoming metal M'X2(Solv) n-2 in a series: acetylacetonate > acetate > chloride > nitrate favors the metal exchange. In the most studied cases the reaction of CdP proceeds along a combined associative-dissociative mechanism. The order of the metal exchange reaction is found to be depending on temperature indicating a change in the contributions of associative and combined routes. The "pure" associative reaction mechanism in a medium of DMSO was for the first time found for the labile complex CdTPTBP with the saddle-type nonplanar ligand.
METHOD FOR PRODUCING ISOINDOLE AND ISOINDOLE PRODUCED BY THE METHOD FOR PRODUCING ISOINDOLE
-
Page/Page column 23, (2010/11/19)
Disclosed is a method for manufacturing isoindolic compound, which can adopt a condition capable of being put to industrially practical use, which can produce stable isoindolic compound, and which can further produce the isoindolic compound with a high yield. The method for manufacturing isoindolic compound comprises a thermal treatment step where a compound of which molecule includes a structure of pyrrole fused with bicyclo [2.2.2] octadiene skeleton is subjected to a supercritical carbon dioxide atmosphere. The thermal treatment step is preferably performed at a temperature of not less than 50 °C and not more than 300 °C.
Complexation of tetraphenyltetrabenzoporphine with Cu(II), Cd(II), Zn(II), and Co(II) salts in organic solvents
Berezin,Toldina
, p. 573 - 578 (2008/10/09)
The rate and activation parameters of tetraphenyltetrabenzoporphine (H 2TPTBP) complexation with 3d-metal acetates and acetylacetonates are shown to be determined by the solvent nature. With an increase in the electron-donor properties of a solvent, the reaction rate increases due to protonation of N-H bonds and decreases as MAm(Solv)n - m salt solvates become more stable. As the result, the rate of a reaction with ZnAc2 increases in the series: DMF 3CN 6H6. In inert and weakly coordinating solvents, the transition state of a reaction is supposed to be formed according to the mechanism of contraction of the salt coordination sphere. The rate of H2TPTBP reaction with metal acetates in pyridine changes in the series: Cu(II) > Cd(II) > Zn(II) > Co(II), while the stability of the obtained complexes decreases in the series Cu(II) > Co(II) > Zn(II) > Cd(II). It is shown that the spectral criterion of the complex stability can be used in the series of metal complexes with one ligand, but it is violated if the ligand structure is changed.
Trans-effect in kinetics of reactions of mixed solvates of Cu(II) acetate with tetraphenyltetrabenzoporphine in organic solvents
Berezin,Toldina
, p. 579 - 583 (2008/10/09)
The kinetics of complex formation of tetraphenyltetrabenzoporphine with Cu(II) and Zn(II) acetates is studied in individual and mixed coordinating solvents on the basis of DMSO, DMF, and Py. The substantial increase in CuAc2 reactivity in mixed
Complex formation and spectral properties of meso- phenyltetrabenzoporphyrins in pyridine and N,N-dimethylformamide
Berezin,Toldina,Kudrik
, p. 1309 - 1314 (2007/10/03)
Contributions of structural (macroring distortion) and polarization (in asymmetrically substituted derivatives) effects into the reactivity and chromophoric properties of substituted porphyrins were revealed on the basis of the kinetics of complex formation of nona-, deca-, undeca-, and dodecasubstituted porphyrins (meso-phenyltetrabenzoporphyrins) with Zn(OAc) 2 in pyridine and the electronic absorption spectra of the ligands and their complexes with Zn(II) and Cu(II) in pyridine and N,N-dimethylformamide (DMF). Dodecaphenyl substitution produces a weaker ring distortion in the more aromatic tetrabenzoporphyrin compared with porphyrins themselves. Irrespective of the degree of macroring nonplanarity, the Zn (II) and Cu complexes of tetrabenzoporphyrins with increasing degree of meso-phenyl substitution meet a spectral stability criterion.
Synthesis and properties of meso-monophenyltetrabenzoporphine and its zinc complex
Galanin,Kudrik,Shaposhnikov
, p. 1119 - 1122 (2007/10/03)
meso-Monophenyltetrabenzoporphine and its zinc complex were synthesized starting from 3-(3-oxo-2,3-dihydro-1H-isoindol-1-ylidenemethyl)-1H-isoindol-1-one. The effect of unsymmetrical meso-substitution on physical and spectral properties of the products is
