New heterocyclic tetrathiafulvalene compounds with an azobenzene moiety: photomodulation of the electron-donating ability of the tetrathiafulvalene moiety

Guoyong Wen; Deqing Zhang; Yanyan Huang; Rui Zhao; Lingyun Zhu; Zhigang Shuai; Daoben Zhu

doi:10.1021/jo070651e

New heterocyclic tetrathiafulvalene compounds with an azobenzene moiety: photomodulation of the electron-donating ability of the tetrathiafulvalene moiety

J Org Chem. 2007 Aug 3;72(16):6247-50. doi: 10.1021/jo070651e. Epub 2007 Jul 6.

Authors

Guoyong Wen¹, Deqing Zhang, Yanyan Huang, Rui Zhao, Lingyun Zhu, Zhigang Shuai, Daoben Zhu

Affiliation

¹ Beijing National Laboratory for Molecular Sciences, Organic Solids Laboratory, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080, China.

PMID: 17616147
DOI: 10.1021/jo070651e

Abstract

New heterocyclic TTF compounds 1a-c and 2 with an azobenzene moiety were described. The oxidation potential of 1a could be reversibly modulated by alternating UV and visible light irradiation. As a result, a molecular switch with UV/visible light as the inputs and the electrochemical signal as the output was achieved. Moreover, it was found that the influence of the azobenzene photoisomerization on the electronic property of the TTF unit became stronger with shorter spacers in compounds 1a-c.