Synthesis, Characterization, and Photophysical Properties of Triptycene-Based Chiral Organoboranes

Chiral luminescent triptycenes (HC-BN and HC-BB) functionalized with electron-donating carbazole and electron-accepting triarylborane were synthesized by classical Buchwald-coupling and Suzuki-coupling reactions. The compound bearing both carbazole and triarylborane, HC-BN, exhibits significant thermochromic shift of the emission because of the intramolecular charge transfer (ICT) character. Their chiral optical properties, including circular dichroism (CD) and circularly polarized luminescence (CPL), are further studied because of the inherent chirality of triptycene derivatives. This work may contribute to the development of new chiral luminescent materials based on the rigid, homoconjugated, and structurally unusual three-dimensional triptycene scaffolds.