Toggle Main Menu Toggle Search

ePrints

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

Downloads

Full text for this publication is not currently held within this repository. Alternative links are provided below where available.


Abstract

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

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

URL: http://dx.doi.org/10.1016/j.tetlet.2011.08.013

DOI: 10.1016/j.tetlet.2011.08.013


Altmetrics

Altmetrics provided by Altmetric


Actions

    Link to this publication


Share