Bis- and Tris-fused Tetrathiafulvalenes Extended with Anthracene-9,10-diylidene

Abstract

Bis- and tris-fused π-electron donors composed of extended tetrathiafulvalene with anthraquinoid spacers ( 4 and 5 ) were successfully synthesized. X-ray structure analysis of tetrakis(methylthio)- 5 ( 5a ) revealed that the molecule adopted a transoid–cisoid conformation. The cyclic voltammogram of 4a is composed of two pairs of two-electron redox waves, while the cyclic voltammogram of tetrakis(hexylthio) derivative 5b consists of one pair of four-electron redox waves and one pair of two-electron redox waves, respectively. Spectroelectrochemistry of 4a and 1 H NMR spectrum of a 4b salt revealed that two positive charges in 4 2+ are distributed mainly on one TTFAQ (9,10-bis(1,3-dithiol-2-ylidene)-9,10-dihydroanthracene) moiety.