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Synthesis and Strong π-π Interaction of Hexaazatriphenylene Derivatives with Alternating Electron-Withdrawing and -Donating Groups.

Hexaazatriphenylene (HAT) derivatives have attracted wide attention because of their electron-deficient nature and unique self-assembly properties. In this work, a facile synthesis method for obtaining HAT derivatives with alternating electron-withdrawing nitrile and electron-donating alkoxy groups ( HATCNOC n ) is proposed. Crystal structure analysis indicated that HATCNOC n forms a one-dimensional columnar structure via strong π-π interactions. Density functional theory calculations revealed that the edge of HATCNOC n is divided into positively and negatively charged sites owing to the presence of alternating nitrile and alkoxy groups, which would induce strong π-π interactions. Thermal analysis and polarizing optical microscopy revealed that HATCNOC n exhibits columnar liquid-crystal phases. Time-resolved microwave conductivity measurements further demonstrated the photoconductive nature of HATCNOC n . The proposed strategy could provide a new strategy for the design of novel organic semiconductive materials.