Synthesis and characterization of an acenaphthene–fused, π-extended tetrathiafulvalene derivative

Abstract

The π-extended TTF derivative (III) containing fused acenaphthene moieties was synthesized by the P(OMe)3 mediated coupling reaction of acenaphtho[1, 2-d][1, 3]dithiol-8-one (II). Compound II was obtained in 51% yield from 1(2 H)-acenaphthylenone (I) in a single step. Crystal structures of compounds I and II reveal the presence of extended intermolecular π-π stacking interactions in the crystal lattice. TTF derivative III reacted with 7,7,8,8-tetracyanoquinodimethane (TCNQ) to form a charge-transfer complex that exhibited absorption bands at 762 and 859 nm. A simplified molecular orbital diagram for III was established using density functional theory (DFT) to understand electronic transitions.