Synthesis and photophysics of artificial photosynthetic reaction centers with porphyrins as primary electron acceptors

ORGN 228

Stephanie L. Gould, Gerdenis Kodis, Rodrigo Palacios, Linda de la Garza, Devens Gust, Thomas A. Moore, and Ana L. Moore. Department of Chemistry and Biochemistry, The Center for the Study of Early Events in Photosynthesis, Arizona State University, Tempe, AZ 85287-1604
Triads 1 and 2 consisting of a caroteniod (C), a bismesitylporphryin (P/PZn) and tris(heptafluoropropyl)porphyrin (PF) have been synthesized. Photoinduced electron transfer from the first excited singlet state of P, or hole transfer from the first excited singlet state of PF, yields C–P•+–PF•–. Hole transfer from C then yields the final charge separated state C•+–P–PF•– decaying primarily to a triplet-excited state localized on the carotenoid, 3C -P-PF, rather than the ground state. Amphipathic triads bearing a carboxyphenyl-bis(heptafluropropyl)porphyrin (PF-CO2H), 3 and 4, as the primary electron acceptor were also synthesized. Photoinduced electron transfer resulted in photophysical behavior similar to that of 1 and 2. Synthesis and preliminary spectroscopic studies of 4 in a lipid bilayer will be presented.

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