Tetracyanoanthraquinodimethanes Having Biaryl Substituents: Synthesis, Crystal Structures, and Physical Properties

11,11,12,12-Tetracyano-9,10-anthraquinodimethane (TCNAQ) derivatives having four types of aryl substituents, phenyl, biphenyl-4-yl, thien-2-yl, and 2,2'-bithiophen-5-yl groups at their 2-position, were synthesized and characterized. Their crystal structures were determined by single-crystal X-ray structure analysis, revealing that the TCNAQ moiety and electron-donating substituents form donor acceptor-segregated columnar structures. The combination of nonplanar electron acceptor TCNAQ and planar donor units provides a good way to afford segregated columnar structures.