Triphenylamine[3]arenes: streamlining synthesis of a versatile macrocyclic platform for supramolecular architectures and functionalities

• Main Authors: Fang, Wangjian, Zhang, Jianyu, Guo, Minjie, Zhao, Yanli, Sue, Andrew Chi-Hau
• Other Authors: School of Chemistry, Chemical Engineering and Biotechnology
• Format: Article
• Language: English
• Published: 2024
• Subjects: Chemistry; Iodine adsorption; Macrocycle
• Online Access: https://hdl.handle.net/10356/180913
• Institution: Nanyang Technological University

Triphenylamine[3]arenes (TPA[3]s), featuring [16]paracyclophane backbone with alternating carbon and nitrogen bridging atoms, were synthesized through a BF3 ⋅ Et2O-catalyzed cyclization reaction using triphenylamine derivatized monomers and paraformaldehyde. This molecular design yielded a series of TPA[3] macrocycles with high efficiency, with their facile derivatizations also successfully demonstrated. On account of the strong electron-donating properties of the TPA moieties, these TPA[3]s exhibit remarkable delayed fluorescence, and possess a significant affinity for iodine. Furthermore, their inherent three-fold symmetry rendered TPA[3]s as novel building blocks for the construction of extended frameworks and molecular cages. This advancement expands the versatility of discrete macrocycles into complex architectures, enhancing their applicability across a broad spectrum of applications.