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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.
Author(s): Benniston AC, Harriman A, Yang S, Harrington RW
Publication type: Article
Publication status: Published
Journal: Tetrahedron Letters
Print publication date: 07/08/2011
ISSN (print): 0040-4039
ISSN (electronic): 1873-3581
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