Synlett 2017; 28(12): 1422-1426
DOI: 10.1055/s-0036-1588796
letter
© Georg Thieme Verlag Stuttgart · New York

Thieme Chemistry Journal Awardees – Where are They Now?
The Influence of Electron-Withdrawing Groups at the 2- and 2′-Positions of Dibenzothienylethenes on Molecular Switching

Robert Hofsäß, David Rombach, Hans-Achim Wagenknecht*
  • Karlsruhe Institute of Technology (KIT), Institute of Organic Chemistry, Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany   Email: Wagenknecht@kit.edu
Further Information

Publication History

Received: 13 February 2017

Accepted after revision: 28 March 2017

Publication Date:
02 May 2017 (eFirst)

Abstract

Three dibenzothienylethenes that carry a methyl, a trifluoromethyl, or a fluoro substituent in the 2- and 2′-position were synthesised in short multistep syntheses, respectively. The trifluoromethyl and fluoromethyl substituents significantly improve the absorption properties of the corresponding open and closed isomers (both in the UV-A and in the visible range). The increasing electron deficiency (i) enlarges the portion of the closed and coloured diarylethene isomer in the corresponding photostationary states and slows down the closing and opening isomerisation, (ii) the switching reactions, both closing and opening, are slowed down, and (iii) the switching quantum yields are lowered.

Supporting Information