1,3,7-Triazapyrene-Based ortho-Carborane Fluorophores: Convenient Synthesis, Theoretical Studies, and Aggregation-Induced Emission Properties

A convenient transition-metal-free approach, based on nucleophilic substitution of hydrogen (SNH), for consecutive regioselective C–H functionalization of 1,3,7-triazapyrene scaffolds with carboranyllithium and phenyllithium is reported. The theoretical calculations disclosed highlight key features in the regioselectivity and mechanism of the investigated SNH transformations. The novel 1,3,7-triazapyrene-based ortho-carboranes obtained have large potential in the field of molecular electronics as organic luminophores, which are characterized by the aggregation-induced emission and dual-emission effects.

本研究报道了一种基于氢亲核取代（SNH）的便捷无过渡金属策略，可实现1,3,7-三氮芘骨架与碳硼烷基锂、苯基锂的连续区域选择性C-H官能化反应。理论计算揭示了所研究的SNH转化的区域选择性与反应机理的关键特征。所得到的新型1,3,7-三氮芘基邻位碳硼烷，作为兼具聚集诱导发光（aggregation-induced emission）与双发射效应的有机发光体，在分子电子学领域具备广阔应用前景。