Synthesis of a Benzothiadiazole-Based D−A Molecule with Aggregation-Induced Emission and Controlled Assembly Properties

Abstract

An electron-donating−accepting (D−A) molecule, namely, 4-(1-(4-(9H-carbazol-9-yl)phenyl)-1H-1,2,3-triazol-4-yl)benzo[c][1,2,5]thiadiazole (BT-SCC) containing carbazole as the donor moiety and benzothiadiazole as the acceptor moiety is prepared. Single-crystal X-ray structure analysis elucidated the multiple intermolecular interactions, such as hydrogen bonds, CH…π, and π…π interplays. Interestingly, the aggregation-induced emission phenomenon is observed for BT-SCC featured with enhanced fluorescent quantum yield from diluted solution of CH2Cl2 (Φ = ca. 0.1) to CH2Cl2/hexane mixed solutions or solid states (Φ = ca. 0.8). Finally, aggregates of BT-SCC are obtained through precipitating from hot and saturated solutions or solvent-vapor methods and the aggregating morphologies could be easily controlled through different preparation methods. Fabulous cube-like micro-crystals and nanospherical structures are obtained, which is established by the synergistic effects of the multiple non-covalent interactions, endowing potential utility in the field of optoelectronic devices.