Synthesis and Structural Characterization of Carbazole‐Tailored Luminescent Triarylmethyl Radical and its Stable Cation

作者：Chunlin Tang, Yuxin Zhu, Jian Jin, Shuai Zhang, Kang Zhou, Zikai He · 发表于：Angewandte Chemie International Edition · 年份：2024 · DOI：10.1002/anie.202414406 · 被引用次数：9 · 研究领域：Luminescence and Fluorescent Materials、Electron Spin Resonance Studies、Molecular Sensors and Ion Detection

Abstract The development of novel luminescent radicals, characterized by their unique doublet emission, endows a significant challenge. In this study, we reported the synthesis of a luminescent neutral radical, BCzAnM‐R, tailored by two carbazolyl groups and an anthryl group to achieve a nonalternant structure. It exhibited near‐infrared emission with a peak at 1020 nm in toluene. Interestingly, its corresponding cation, BCzAnM‐C, was synthesized through an unconventional SnCl 2 ‐mediated reduction‐aromatization‐oxidation reaction in one‐pot and gram‐scale. The cation demonstrated remarkable stability for up to weeks in ambient conditions and facilitated the silica‐gel chromatography isolation as an organic salt with SnCl 3 − as the counter ion. The carbazolyl groups effectively modulate molecular structures, photophysical properties, and stabilities. Notably, BCzAnM‐R represents the first luminescent triarylmethyl radical with two carbazolyl groups directly attached to the central carbon.