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SYNTHESIS OF AMPHIPATHIC PORPHYRINS AND THEIR PHOTOINDUCED ELECTRON TRANSFER REACTIONS AT THE LIPID BILAYER‐WATER INTERFACE
Author(s) -
Hwang Kuo Chu,
Mauzerall David,
Wagner Richard W.,
Lindsey Jonathan S.
Publication year - 1994
Publication title -
photochemistry and photobiology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.818
H-Index - 131
eISSN - 1751-1097
pISSN - 0031-8655
DOI - 10.1111/j.1751-1097.1994.tb05014.x
Subject(s) - porphyrin , chemistry , photochemistry , viologen , bilayer , electron acceptor , photoinduced electron transfer , electron transfer , acceptor , ionic strength , amphiphile , ionic bonding , electron donor , lipid bilayer , ion , membrane , organic chemistry , copolymer , catalysis , aqueous solution , biochemistry , condensed matter physics , polymer , physics
Abstract A one flask synthesis of cis ‐substituted amphipathic porphyrins is reported. These porphyrins were used to study electrostatic effects on photoinduced electron transfer across the lipid bilayer‐water interface. A neutral porphyrin undergoes only dynamic interfacial electron transfer reactions irrespective of charge of the acceptor, although ionic strength effects indicate a negative charge on the porphyrin donor species. A dianionic porphyrin forms an interfacial static complex with a dicationic electron acceptor, methyl viologen, at low ionic strength. The electron transfer rate within the complex is slow, 10 5 ∼ 10 6 s ‐1 , which is attributed to a near orthogonal orientation between the donor and the acceptor ∼ orbitals.