Supramolecular triads bearing porphyrin and fullerene via 'two-point' binding involving coordination and hydrogen bonding

被引:42
作者
D'Souza, F
El-Khouly, ME
Gadde, S
Zandler, ME
McCarty, AL
Araki, Y
Ito, O
机构
[1] Wichita State Univ, Dept Chem, Wichita, KS 67260 USA
[2] Tohoku Univ, Inst Multidisciplinary Res Adv Mat, Sendai, Miyagi 9808577, Japan
[3] Tohoku Univ, Dept Chem, Grad Sch Sci, Sendai, Miyagi 9808587, Japan
基金
美国国家卫生研究院;
关键词
D O I
10.1016/j.tet.2005.05.112
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Supramolecular triads composed of fullerene, (C-60) as primary electron acceptor, zinc porphyrin (ZnP) as primary electron donor, and either a ferrocene (Fc), or N,N-dimethylaminophenyl (DMA), or N,N-diphenylaminophenyl (DPA) entity as a second electron donor were constructed via a 'two-point' binding motif involving axial coordination and hydrogen bonding. The B3LYP/3-21G(*) optimized structures revealed disposition of the three entities of the triads in a triangular fashion. The redox behavior of the different components was studied using cyclic voltammetry in o-dichlorobenzene containing 0.1 M (n-C4H9)(4)NClO4. The oxidation potentials of the second electron donor followed the trend: Fc < DMA < DPA, and the free-energy calculations Suggested the possibility of the occurrence of sequential hole transfer in these triads. Efficient electron transfer from the excited singlet state of zinc porphyrin to the fullerene entity was observed in all of the studied triads in o-dichlorobenzene. Longer charge-separated states were observed for zinc porphyrin with a carboxylic acid compared with that having an amide group. The ratios of the experimentally determined forward to reverse electron transfer rates, k(CS)/k(CR) were evaluated to be 10(3) for triads formed by zinc porphyrin with a carboxylic acid, suggesting charge stabilization in these triads. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1967 / 1978
页数:12
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