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

Abstract: 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 (<bold>APyS</bold> and <bold>APySe</bold>) and azaacenes (<bold>PyP</bold>, <bold>PyTh</bold>, <bold>PyPy</bold>, <bold>PyPh</bold>, and <bold>PyAP</bold>) 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. [ABSTRACT FROM AUTHOR]