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Spring Open Two-plus-Two Electron Storage in a Disulfide-Strapped Methyl Viologen Derivative

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.

Publication metadata

Author(s): Benniston AC, Hagon J, He XY, Yang SJ, Harrington RW

Publication type: Article

Publication status: Published

Journal: Organic Letters

Year: 2012

Volume: 14

Issue: 2

Pages: 506-509

Print publication date: 05/01/2012

ISSN (print): 1523-7060

ISSN (electronic): 1523-7052

Publisher: American Chemical Society


DOI: 10.1021/ol203099h


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Funder referenceFunder name
Newcastle University
EP/G04094X/1Engineering and Physical Sciences Research Council