Boron-containing monopyrrolo-annelated tetra thiafulvalene compounds: synthesis and absorption spectral/electrochemical responsiveness toward fluoride ion

J Org Chem. 2010 Aug 6;75(15):5330-3. doi: 10.1021/jo1007306.

Abstract

Two new boron-based conjugated compounds 1 and 2 containing one and three monopyrrolo-annelated tetrathiafulvalene (TTF) unit(s) were synthesized and characterized. They exhibit typical ICT absorptions which can be modulated after addition of fluoride ion. In addition, the oxidation potentials of 1 and 2 are shifted to low potential region in the presence of fluoride ion. Such absorption spectral and electrochemical responsiveness of 1 and 2 toward fluoride ion is due to the binding of the boron units with fluoride ion.