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Updated: Jun 11, 2025

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
Published on: April 19, 2019
Synthesis and Structural Characterization of Carbazole-Tailored Luminescent Triarylmethyl Radical and its Stable
Chunlin Tang1,2, Yuxin Zhu1, Jian Jin1
1School of Science, Harbin Institute of Technology, Shenzhen, Shenzhen, Guangdong, 518055, China.
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 SnCl2-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 SnCl3 - 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.
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