SYNTHESIS AND INTRAMOLECULAR CHARGE SEPARATION OF FIXED-DISTANCE TRIADS CONSISTING OF ZINC PORPHYRIN, METAL-FREE PORPHYRIN, AND ELECTRON-ACCEPTING DIIMIDE MOIETY

被引:41
作者
OSUKA, A [1 ]
ZHANG, RP [1 ]
MARUYAMA, K [1 ]
OHNO, T [1 ]
NOZAKI, K [1 ]
机构
[1] OSAKA UNIV, COLL GEN EDUC, DEPT CHEM, TOYONAKA, OSAKA 560, JAPAN
关键词
D O I
10.1246/bcsj.66.3773
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Synthesis of fixed-distance triads consisting of zinc porphyrin (ZnP), metal-free porphyrin (H2P), and pyromellitimide (PIm) or 1,4:5,8-naphthalenetetracarboximide (NIm) is described. The ZnP and H2P moieties are bridged by aromatic spacers such as 1,4-phenylene, 4,4'-biphenylylene, methylenebis(1,4-phenylene), and bicyclo[2.2.2]octane-1,4-diylbis(1,4-phenylene) groups. The steady-state fluorescence spectra indicated the occurrence of intramolecular singlet-singlet energy transfer form the ZnP to the H2P. Formation of long-lived charge-separated states (ZnP)+-H2P-(PIM)- and (ZnP)+-H2P-(NIm)- with lifetimes of 0.14-80 mus in THF was observed by nanosecond to microsecond transient absorption spectroscopy. The lifetimes of the (ZnP)+-H2P-(Im)- states depend on the distances between the charged sites as well as the energy gaps between the ion pair and the ground state.
引用
收藏
页码:3773 / 3782
页数:10
相关论文
共 24 条
[1]   STRUCTURE OF THE REACTION CENTER FROM RHODOBACTER-SPHAEROIDES R-26 - THE COFACTORS .1. [J].
ALLEN, JP ;
FEHER, G ;
YEATES, TO ;
KOMIYA, H ;
REES, DC .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1987, 84 (16) :5730-5734
[2]   INTRAMOLECULAR PHOTOINDUCED CHARGE SEPARATION AND CHARGE RECOMBINATION OF THE PRODUCT ION-PAIR STATES OF A SERIES OF FIXED-DISTANCE DYADS OF PORPHYRINS AND QUINONES - ENERGY-GAP AND TEMPERATURE DEPENDENCES OF THE RATE CONSTANTS [J].
ASAHI, T ;
OHKOHCHI, M ;
MATSUSAKA, R ;
MATAGA, N ;
ZHANG, RP ;
OSUKA, A ;
MARUYAMA, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (13) :5665-5674
[3]   STRUCTURE OF RHODOPSEUDOMONAS-SPHAEROIDES R-26 REACTION CENTER [J].
CHANG, CH ;
TIEDE, D ;
TANG, J ;
SMITH, U ;
NORRIS, J ;
SCHIFFER, M .
FEBS LETTERS, 1986, 205 (01) :82-86
[4]   PREPARATION OF 4-SUBSTITUTED 1-METHOXYCARBONYLBICYCLO 2.2.2!OCTANES, SUBSTITUTED 1-PHENYLBICYCLO 2.2.2!OCTANES, 4-SUBSTITUTED 1-PARA-NITROPHENYLBICYCLO 2.2.2!OCTANES, AND 1,4-DISUBSTITUTED BICYCLO 2.2.2!OCTANES [J].
CHAPMAN, NB ;
SOTHEESW.S ;
TOYNE, KJ .
JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (04) :917-&
[5]   PYROMELLITIMIDE-BRIDGED PORPHYRINS AS MODEL PHOTOSYNTHETIC SYSTEMS .1. SYNTHESIS AND STEADY-STATE FLUORESCENCE PROPERTIES [J].
COWAN, JA ;
SANDERS, JKM .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (11) :2435-2437
[6]   X-RAY STRUCTURE-ANALYSIS OF A MEMBRANE-PROTEIN COMPLEX - ELECTRON-DENSITY MAP AT 3A RESOLUTION AND A MODEL OF THE CHROMOPHORES OF THE PHOTOSYNTHETIC REACTION CENTER FROM RHODOPSEUDOMONAS-VIRIDIS [J].
DEISENHOFER, J ;
EPP, O ;
MIKI, K ;
HUBER, R ;
MICHEL, H .
JOURNAL OF MOLECULAR BIOLOGY, 1984, 180 (02) :385-398
[7]   MIMICKING PHOTOSYNTHESIS [J].
GUST, D ;
MOORE, TA .
SCIENCE, 1989, 244 (4900) :35-41
[8]   MOLECULAR MIMICRY OF PHOTOSYNTHETIC ENERGY AND ELECTRON-TRANSFER [J].
GUST, D ;
MOORE, TA ;
MOORE, AL .
ACCOUNTS OF CHEMICAL RESEARCH, 1993, 26 (04) :198-205
[9]   PRIMARY PHOTOCHEMISTRY OF REACTION CENTERS FROM THE PHOTOSYNTHETIC PURPLE BACTERIA [J].
KIRMAIER, C ;
HOLTEN, D .
PHOTOSYNTHESIS RESEARCH, 1987, 13 (03) :225-260
[10]   A CHEMICAL APPROACH TOWARD PHOTOSYNTHETIC REACTION CENTER [J].
MARUYAMA, K ;
OSUKA, A .
PURE AND APPLIED CHEMISTRY, 1990, 62 (08) :1511-1520