Substitution-position-dependent optoelectronic properties of methylthiolated anthracenes

Abstract

Anthracenes have become some of the most important organic semiconducting materials owing to their high stability and superior mobility. Although methylthio-functionalization is a powerful strategy to tailor packing arrangement, substitution-position-dependent optoelectronic properties have not been investigated in anthracenes. Herein, we synthesized three anthracene derivatives by introducing methylthio groups at different positions. Compared with 9,10- and 2,6,9,10-substitution, 2,6-substitution gives rise to a close packing arrangement with favourable charge transport. In addition, 1D mixed-stack donor–acceptor cocrystals based on methylthioanthracenes and tetracyanoquinodimethane were prepared, exhibiting good n-type charge transport behaviour.