Electron transfer within self-assembling cyclic tetramers using chlorophyll-based donor-acceptor building blocks

Journal of the American Chemical Society
Victoria L GundersonMichael R Wasielewski

Abstract

The synthesis and photoinduced charge transfer properties of a series of Chl-based donor-acceptor triad building blocks that self-assemble into cyclic tetramers are reported. Chlorophyll a was converted into zinc methyl 3-ethylpyrochlorophyllide a (Chl) and then further modified at its 20-position to covalently attach a pyromellitimide (PI) acceptor bearing a pyridine ligand and one or two naphthalene-1,8:4,5-bis(dicarboximide) (NDI) secondary electron acceptors to give Chl-PI-NDI and Chl-PI-NDI(2). The pyridine ligand within each ambident triad enables intermolecular Chl metal-ligand coordination in dry toluene, which results in the formation of cyclic tetramers in solution, as determined using small- and wide-angle X-ray scattering at a synchrotron source. Femtosecond and nanosecond transient absorption spectroscopy of the monomers in toluene-1% pyridine and the cyclic tetramers in toluene shows that the selective photoexcitation of Chl results in intramolecular electron transfer from (1*)Chl to PI to form Chl(+•)-PI(-•)-NDI and Chl(+•)-PI(-•)-NDI(2). This initial charge separation is followed by a rapid charge shift from PI(-•) to NDI and subsequent charge recombination of Chl(+•)-PI-NDI(-•) and Chl(+•)-PI-(NDI)NDI(-•) on a ...Continue Reading

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Citations

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