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

Autor: Tang C; School of Science, Harbin Institute of Technology, Shenzhen, Shenzhen, Guangdong, 518055, China.; School of Chemical Engineering and Technology, Harbin Institute of Technology, Harbin, Heilongjiang, 150001, China., Zhu Y; School of Science, Harbin Institute of Technology, Shenzhen, Shenzhen, Guangdong, 518055, China., Jin J; School of Science, Harbin Institute of Technology, Shenzhen, Shenzhen, Guangdong, 518055, China., Zhang S; School of Science, Harbin Institute of Technology, Shenzhen, Shenzhen, Guangdong, 518055, China.; School of Chemical Engineering and Technology, Harbin Institute of Technology, Harbin, Heilongjiang, 150001, China., Zhou K; Hoffman Institute of Advanced Materials, Shenzhen Polytechnic University, Shenzhen, Guangdong, 518055, China., He Z; School of Science, Harbin Institute of Technology, Shenzhen, Shenzhen, Guangdong, 518055, China.; School of Chemical Engineering and Technology, Harbin Institute of Technology, Harbin, Heilongjiang, 150001, China.
Jazyk: angličtina
Zdroj: Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2024 Oct 04, pp. e202414406. Date of Electronic Publication: 2024 Oct 04.
DOI: 10.1002/anie.202414406
Abstrakt: 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.
(© 2024 Wiley-VCH GmbH.)
Databáze: MEDLINE
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