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

Smyshliaeva, Lidia A.; Вараксин, Михаил В.; Fomina, Ekaterina I.; Medvedeva, M. V.; Свалова, Т. С.; Козицина, А. Н.; Демидов, О. П.; Боровлев, И. В.; Mensch, Carl; Mampuys, Pieter; Maes, Bert U. W.; Charushin, Valery N.; Чупахин, О. Н.

doi:10.1021/acs.organomet.1c00234

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Cited by 8 publications

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Synthesis of Triazabenzo[a]pyrenes and Their Photophysical, Acid‐Responsive, and Electrochemical Properties

et al. 2022

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A series of triazabenzo [a]pyrenes comprising a cata-condensed pyridine ring and 4,10-diazapyrene framework were synthesized from commercially available materials in the following three steps: palladium-catalyzed direct CÀ H arylation, nucleophilic addition of Grignard reagents to cyano groups, and copper-catalyzed oxidative CÀ N bond formation. The triazabenzo[a]pyrenes showed superior electron-accepting properties and narrower HOMO-LUMO energy gaps compared to the corresponding 4,10-diazapyrene derivative because of the condensation of an electron-deficient pyridine ring. The photophysical, acid-responsive, and electrochemical properties of triazabenzo[a]pyrenes depend on the position of the nitrogen atom in the cata-condensed pyridine ring. Density functional theory calculations revel that the condensation of a pyridine ring leads to a lowering of the LUMO energy level thereby enhancing the electron-accepting properties.

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