TTF and TCNQ analogues derived from a new benzo-fused thiopyranyl building block

TTF-type and TCNQ-type analogues (9–12) have been prepared from a new benzo-fused thiopyranyl precursor 8. The synthetic conditions of 8 were optimized. An anomaly was observed in the 1H NMR spectrum of 9. The crystal structures of 9 and 10 show distorted conformations and ordered packing geometries connected by short contacts. Electronic and redox properties of 9–12 were investigated by UV–vis spectroscopy and cyclic voltammetry. Both 9 and 10 exhibited p-type OFET performances.

Graphical abstractA class of TTF and TCNQ analogues have been synthesized from a new benzo-fused thiopyranyl building block–thiopyrano[3,2-h]thiochromene-4,7-dione.Figure optionsDownload full-size imageDownload as PowerPoint slide