title: Synthesis of amphipathic porphyrins and their photoinduced electron transfer reactions at the lipid bilayer-water interface.
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) approximately 10(6) s-1, which is attributed to a near orthogonal orientation between the donor and the acceptor pi orbitals.
authors.affiliation: Rockefeller University, New York, NY 10021.
authors.forename: K C
authors.initials: KC
authors.lastname: Hwang
authors.forename: D
authors.initials: D
authors.lastname: Mauzerall
authors.forename: R W
authors.initials: RW
authors.lastname: Wagner
authors.forename: J S
authors.initials: JS
authors.lastname: Lindsey
mesh_terms: D004563:Electrochemistry; D004579:Electron Transport; D008051:Lipid Bilayers / Q000737:chemistry; D010777:Photochemistry; D011166:Porphyrins / Q000138:chemical synthesis* / Q000737:chemistry / Q000528:radiation effects*; D014867:Water / Q000737:chemistry
chemical_list: D008051:Lipid Bilayers; D011166:Porphyrins; D014867:Water