First stable tetracyanodiphenoquinodimethane with a completely planar geometry: Preparation, X-ray structure, and highly conductive complexes of bis[1,2,5]thiadliazolo-TCNDQ

The titled tetracyanodiphenoquinodimethane (TCNDQ) derivative was newly des igned and prepared as a novel component for highly conductive organic mater ials. Introduction of 1,2,5-thiadiazole rings into the TCNDQ skeleton leads to large stabilization in the neutral state. X-ray analysis bas:revealed t heir structural details which suggest that interatomic interactions (C-H .. . N, S ... N) play an important role in determining the molecular and cryst al structure. The novel electron acceptor shows strong electron affinity co mparable with that of TCNQ, and gave highly conductive charge-transfer (CT) complexes and an anion radical salt. (C) 1999 Elsevier Science Ltd. All ri ghts reserved.