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.
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Organic & Biomolecular Chemistry
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