Design and synthesis of benzimidazole phenol-porphyrin dyads for the study of bioinspired photoinduced proton-coupled electron transfer

Mora, S. Jimena; Heredia, Daniel A.; Odella, Emmanuel; Vrudhula, Uma; Gust, Devens; Moore, Thomas A.; Moore, Ana L.

doi:10.1142/s1088424619501189

Design and synthesis of benzimidazole phenol-porphyrin dyads for the study of bioinspired photoinduced proton-coupled electron transfer

Journal Article · Thu Jan 16 00:00:00 EST 2020 · Journal of Porphyrins and Phthalocyanines

DOI:https://doi.org/10.1142/s1088424619501189· OSTI ID:1800067

Mora, S. Jimena ^[1]; Heredia, Daniel A. ^[2]; Odella, Emmanuel ^[3]; Vrudhula, Uma ^[3]; Gust, Devens ^[3]; Moore, Thomas A. ^[3]; Moore, Ana L. ^[3]

Arizona State Univ., Tempe, AZ (United States); OSTI
Universidad Nacional de Río Cuarto (Argentina)
Arizona State Univ., Tempe, AZ (United States)

Benzimidazole phenol-porphyrin dyads have been synthesized to study proton-coupled electron transfer (PCET) reactions induced by photoexcitation. High-potential porphyrins have been chosen to model P680, the photoactive chlorophyll cluster of photosynthetic photosystem II (PSII). They have either two or three pentafluorophenyl groups at the meso positions to impart the high redox potential. The benzimidazole phenol (BIP) moiety models the Tyr_z-His190 pair of PSII, which is a redox mediator that shuttles electrons from the water oxidation catalyst to P680^∙+. The dyads consisting of a porphyrin and an unsubstituted BIP are designed to study one-electron one-proton transfer (E1PT) processes upon excitation of the porphyrin. When the BIP moiety is substituted with proton-accepting groups such as imines, one-electron two-proton transfer (E2PT) processes are expected to take place upon oxidation of the phenol by the excited state of the porphyrin. The bis-pentafluorophenyl porphyrins linked to BIPs provide platforms for introducing a variety of electron-accepting moieties and/or anchoring groups to attach semiconductor nanoparticles to the macrocycle. The triads thus formed will serve to study the PCET process involving the BIPs when the oxidation of the phenol is achieved by the photochemically produced radical cation of the porphyrin.

View Accepted Manuscript (DOE)

Research Organization:: Arizona State University, Tempe, AZ (United States)

Sponsoring Organization:: USDOE Office of Science (SC)

Grant/Contract Number:: FG02-03ER15393

OSTI ID:: 1800067

Journal Information:: Journal of Porphyrins and Phthalocyanines, Journal Name: Journal of Porphyrins and Phthalocyanines Journal Issue: 11n12 Vol. 23; ISSN 1088-4246

Publisher:: World ScientificCopyright Statement

Country of Publication:: United States

Language:: English

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Design and synthesis of benzimidazole phenol-porphyrin dyads for the study of bioinspired photoinduced proton-coupled electron transfer

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