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Highly-Strained Cyclophanes Bearing Both Photo- and Electro-Active Constituents

Lookup NU author(s): Professor Andrew Benniston, Emeritus Professor Anthony Harriman, Dr Songjie Yang, Dr Ross Harrington


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The synthesis of a highly-strained cyclophane comprising azobenzene and methyl viologen units was achieved by coupling 3,3’-dihydroxy-4,4’-bipyridine with azobenzoic acid in CH2Cl2. The molecular structure, determined by single-crystal X-ray crystallography, shows that the azobenzene N=N unit adopts the trans conformation and that the bipyridinium unit is twisted. The cyclic voltammogram recorded for the target compound displays an irreversible wave at –0.37 V vs Ag/AgCl, associated with the one-electron reduction of the bipyridinium subunit. A further wave is seen at E1/2 = –1.52 V vs Ag/AgCl and is assigned to one-electron reduction of the azobenzene group. Visible light illumination of the azobenzene chromophore in CH3CN triggers trans to cis isomerization but the process is irreversible.

Publication metadata

Author(s): Benniston AC, Harriman A, Yang S, Harrington RW

Publication type: Article

Publication status: Published

Journal: Tetrahedron Letters

Year: 2011

Volume: 52

Issue: 41

Pages: 5315-5318

Print publication date: 07/08/2011

ISSN (print): 0040-4039

ISSN (electronic): 1873-3581

Publisher: Pergamon


DOI: 10.1016/j.tetlet.2011.08.013


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Funder referenceFunder name
EP/G0409X/1Engineering and Physical Sciences Research Council (EPSRC)
EP/F03637X/1Engineering and Physical Sciences Research Council (EPSRC)