Highly-Strained Cyclophanes Bearing Both Photo- and Electro-Active Constituents
- Lookup NU author(s)
- Professor Andrew Benniston
- Professor Anthony Harriman
- Dr Songjie Yang
- Dr Ross Harrington
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| Author(s) | | Benniston AC, Harriman A, Yang S, Harrington RW |
| Publication type | | Article |
| Journal | | Tetrahedron Letters |
| Year | | 2011 |
| Volume | | 52 |
| Issue | | 41 |
| Pages | | 5315-5318 |
| ISSN (print) | | 0040-4039 |
| ISSN (electronic) | | 1873-3581 |
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| Full text for this publication is not currently held within this repository. Alternative links are provided below where available. |
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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. |
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| Publisher | | Pergamon |
| URL | | http://dx.doi.org/10.1016/j.tetlet.2011.08.013 |
| DOI | | 10.1016/j.tetlet.2011.08.013 |
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