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

  1. Lookup NU author(s)
  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
ISSN (print)0040-4039
ISSN (electronic)1873-3581
Full text for this publication is not currently held within this repository. Alternative links are provided below where available.
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.
Actions    Link to this publication

Altmetrics provided by Altmetric