Synthesis, Crystal Analysis, and Optoelectronic Properties of Diazole-Functionalized Acenes and Azaacenes.

Doping heteroatoms into the skeletons of parent acenes can provide more opportunities to construct novel thermally and photostable organic π-conjugated semiconductors. Herein, a family of diazole-decorated acenes (APyS and APySe) and azaacenes (PyP, PyTh, PyPy, PyPh, and PyAP) have been successfully synthesized through the classical reactions. Single-crystal X-ray analyses showed that these as-formed diazole-modified derivatives adopted a twisted topology configuration, whereas the azaacenes display reclining-chair architectures, besides a twisted structure. All these compounds displayed yellow or red light in solution. Moreover, their electrochemical behaviors were also examined. We also found that the azaacenes exhibited a positive spectroscopic response to acid.