Discogens Possessing Aryl Side Groups Synthesized by Suzuki Coupling of Triphenylene Triflates and Their Self-Organization Behavior

Pd-catalyzed Suzuki cross-coupling reactions between arylboronic acids and bromoarenes have been applied widely in the synthesis of liquid-crystalline materials. However, aryl triflate derivatives have been less used despite their high chemical tolerance, reactivity, and chemical accessibility. In this report, three series of discogens have been synthesized in good yields from appropriate triphenylene triflate precursors by Suzuki coupling reactions with various commercial arylboronic acids (e.g., aryl = phenylene, thiophene, naphthalene, triarylamine, carbazole, and fluorene). The synthesized discogens display broad mesophase ranges and high thermal stabilities. Moreover, those bearing triarylamine, carbazole, and fluorene side groups are also blue-light emitters. The availability of the triflate precursors coupled with their highly efficient cross-coupling with commercial arylboronic acids make this strategy extremely versatile and attractive for the design of new functional materials.