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

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  2. Professor Andrew Benniston
  3. Professor Anthony Harriman
  4. Dr Songjie Yang
  5. Dr Ross Harrington
Author(s)Benniston AC, Harriman A, Yang S, Harrington RW
Publication type Article
JournalTetrahedron Letters
Year2011
Volume52
Issue41
Pages5315-5318
ISSN (print)0040-4039
ISSN (electronic)1873-3581
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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.
PublisherPergamon
URLhttp://dx.doi.org/10.1016/j.tetlet.2011.08.013
DOI10.1016/j.tetlet.2011.08.013
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