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Issue 6, 2009
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Through-bond photoinduced electron transfer in a porphyrin-fullerene conjugate held by a Hamilton type hydrogen bonding motif

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Abstract

Control over the occurrence of through-bond electron transfer in self-assembled donor–acceptor conjugates is often difficult, since through-space electron transfer also competes due to the flexible nature of the spacer used to link the entities. In the present study, we have constructed a self-assembled donor–acceptor conjugate held solely by complementary hydrogen bonding and established through-bond electron transfer. The protocol used here is a Hamilton type hydrogen bonding motif involving self-assembly of a carboxylic acid functionalized porphyrin and 2-aminopyridine functionalized fullerene. Owing to the presence of two-point hydrogen bonds, the structure of the dyad is free from rotation with a donor–acceptor distance positioned appropriately to justify the through-bond electron transfer. Detailed spectral, computational and photochemical studies reveal efficient photoinduced charge separation and slow charge recombination in the studied conjugate, thus, bringing out the fundamental advantages of the directional hydrogen-bonding in the construction of donor–acceptor conjugates based on biomimetic principles and their functional role in governing electron transfer events.

Graphical abstract: Through-bond photoinduced electron transfer in a porphyrin-fullerene conjugate held by a Hamilton type hydrogen bonding motif

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Article information


Submitted
12 Dec 2008
Accepted
09 Jan 2009
First published
27 Jan 2009

Org. Biomol. Chem., 2009,7, 1076-1080
Article type
Paper

Through-bond photoinduced electron transfer in a porphyrin-fullerene conjugate held by a Hamilton type hydrogen bonding motif

F. D'Souza, G. M. Venukadasula, K. Yamanaka, N. K. Subbaiyan, M. E. Zandler and O. Ito, Org. Biomol. Chem., 2009, 7, 1076
DOI: 10.1039/B822362A

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