Trifluoromethylation of Anthraquinones for n-Type Organic Semiconductors in Field Effect Transistors.

Abstract

This study puts forth a new design of n-type organic semiconductors, which has trifluoromethylethynyl groups attached to 9,10-anthraquinone at different positions. These electron-deficient anthraquinones are synthesized by trifluoromethylation of the corresponding trimethylsilyl-protected alkynes with fluoroform-derived CuCF3, and their π-π stacking in the crystals is tunable by varying the positions of trifluoromethylethynyl groups. It is found that most of these trifluoromethylated anthraquinones function as n-type semiconductors in solution-processed field effect transistors with electron mobility of up to 0.28 cm2 V-1 s-1.