Lookup NU author(s): Professor Andrew Benniston,
Dr Jerry Hagon,
Dr Ross Harrington
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The synthesis of a disulfide-strapped viologen derivative is described starting from 4,4'-bipyridinyl-3,3'-diol. The first two one-electron reduction potentials, as determined by cyclic voltammetry, occur at E-1/2 = 0.03 V and E-1/2 = -0.16 V vs Ag/AgCl. This is accompanied by two more well separated one-electron reductions at E-1/2 = -1.26 V and E-1/2 = -1.54 V vs Ag/AgCl and the breaking of the disulfide bridge. To alleviate electrostatic repulsion between the two thiolate ions the molecular system must twist or "spring open" to accommodate the final two electrons.
Author(s): Benniston AC, Hagon J, He XY, Yang SJ, Harrington RW
Publication type: Article
Publication status: Published
Journal: Organic Letters
Print publication date: 05/01/2012
ISSN (print): 1523-7060
ISSN (electronic): 1523-7052
Publisher: American Chemical Society
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