Synthesis of β-linked diporphyrins and their homo- and hetero-bimetallic complexes

被引:62
作者
Zhou, X [1 ]
Chan, KS [1 ]
机构
[1] Chinese Univ Hong Kong, Dept Chem, Shatin, New Territories, Peoples R China
关键词
D O I
10.1021/jo971267s
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
beta-Meta-and -para-linked diporphyrins have been synthesized from two complementary routes using Suzuki cross-coupling and Adler condensation. Porphyrin boronate 6 cross couples with beta-monobromoporphyrin 2 to give unsymmetrically substituted porphyrin dimer 7c in high yield, and Adler condensation of beta-formylphenyltetraphenylporphyrins 9b,c with aryl aldehydes yields electronically tunable diporphyrins 7a-e. The home-and hetero-bimetallic complexes 11a-c have been synthesized. Selective mono-metalation with zinc acetate at the beta-substituted site has been found for 7a. The Zn-Co diporphyrin complex 11c undergoes strong emission quenching compared to that of the diporphyrin 11a and dizinc diporphyrin 11b.
引用
收藏
页码:99 / 104
页数:6
相关论文
共 77 条
[51]   A 1,2-PHENYLENE-BRIDGED PORPHYRIN DIMER - SYNTHESIS, PROPERTIES, AND MOLECULAR-STRUCTURE [J].
OSUKA, A ;
NAKAJIMA, S ;
NAGATA, T ;
MARUYAMA, K ;
TORIUMI, K .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1991, 30 (05) :582-584
[52]   SYNTHESIS OF 1,2-PHENYLENE-BRIDGED DIPORPHYRIN LINKED WITH PORPHYRIN MONOMER AND ITS INTRAMOLECULAR SINGLET-SINGLET EXCITATION-ENERGY TRANSFER [J].
OSUKA, A ;
KOBAYASHI, F ;
NAKAJIMA, S ;
MARUYAMA, K ;
YAMAZAKI, I ;
NISHIMURA, Y .
CHEMISTRY LETTERS, 1993, (01) :161-164
[53]   PATHWAY OF PROTON-TRANSFER IN BACTERIAL REACTION CENTERS - REPLACEMENT OF GLUTAMIC-ACID 212 IN THE L-SUBUNIT BY GLUTAMINE INHIBITS QUINONE (SECONDARY ACCEPTOR) TURNOVER [J].
PADDOCK, ML ;
RONGEY, SH ;
FEHER, G ;
OKAMURA, MY .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1989, 86 (17) :6602-6606
[54]   A NOVEL-APPROACH TO THE SYNTHESIS OF SYMMETRICAL AND UNSYMMETRICAL PORPHYRIN DIMERS [J].
PANDEY, RK ;
FORSYTH, TP ;
GERZEVSKE, KR ;
LIN, JJ ;
SMITH, KM .
TETRAHEDRON LETTERS, 1992, 33 (37) :5315-5318
[55]   CIS-TRANS ISOMERIZATION AND ATROPISOMERISM OF OCTAETHYL 1,2-BIS(COPROPORPHYRINYL)ETHYLENE ESTER [J].
PONOMAREV, GV ;
BOROVKOV, VV ;
SHULGA, AM ;
SAKATA, Y .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (17) :1927-1928
[56]   PICOSECOND STUDIES OF QUINONE-SUBSTITUTED MONOMETALLATED PORPHYRIN DIMERS - EVIDENCE FOR SUPEREXCHANGE-MEDIATED ELECTRON-TRANSFER IN A PHOTOSYNTHETIC MODEL SYSTEM [J].
RODRIGUEZ, J ;
KIRMAIER, C ;
JOHNSON, MR ;
FRIESNER, RA ;
HOLTEN, D ;
SESSLER, JL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (05) :1652-1659
[57]  
RUHLMANN L, 1994, J CHEM SOC CHEM COMM, P2394
[58]  
SEEMAN W, 1931, J AM CHEM SOC, V53, P711
[59]   MODELS FOR THE PHOTOSYNTHETIC REACTION CENTER - SYNTHESIS AND STRUCTURE OF PORPHYRIN DIMERS WITH CIS-ETHENE AND TRANS-ETHENE AND SKEWED HYDROXY-METHYLENE BRIDGES [J].
SENGE, MO ;
GERZEVSKE, KR ;
VICENTE, MGH ;
FORSYTH, TP ;
SMITH, KM .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1993, 32 (05) :750-753
[60]   STRUCTURE AND CONFORMATION OF PHOTOSYNTHETIC PIGMENTS AND RELATED-COMPOUNDS .6. THE 1ST CRYSTAL-STRUCTURE OF A COVALENTLY-LINKED CHLORIN DIMER - 20,20'-ETHYLENEBIS(TRANS-2,3,7,8,12,13,17,18-OCTAETHYLCHLORIN) [J].
SENGE, MO ;
HOPE, H ;
SMITH, KM .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1993, (01) :11-16