We report the synthesis and properties of a series of novel triphenylenedicarboxyimides and thioimides (4−6) to probe the effect of thionation on the formation of columnar mesophases. These materials display broad columnar mesophases and high clearing points and self-associate in solution to form dimers. Overall, thionation improved the self-assembly in solution and led to a stabilization of the columnar mesophase. Furthermore, increasing the thionation of these materials led to a lowering of the lowest unoccupied molecular orbital (LUMO) energy level and a narrowing of the highest occupied molecular orbital−LUMO gap.
Nickel-mediated Yamamoto coupling provides a concise and efficient synthesis of triphenylene derivatives, including electron-deficient discotic mesogens.
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