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Triazole‐fused indolo[2,3‐ a ]carbazoles: synthesis, structures, and properties
Author(s) -
Ghosh Sirina,
Das Sarasija,
Kumar Chandan,
Kumar Neha Rani,
Agrawal Abhijeet R.,
Karmakar Himadri S.,
Ghosh Nani Gopal,
Zade Sanjio S.
Publication year - 2020
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.3974
Subject(s) - carbazole , chemistry , bromine , solvatochromism , moiety , halogenation , substituent , pyrrole , triazole , indolizine , indole test , ring (chemistry) , density functional theory , 1,2,4 triazole , medicinal chemistry , combinatorial chemistry , stereochemistry , photochemistry , molecule , organic chemistry , computational chemistry
The synthesis, structure, and photophysical and electrochemical properties of triazole fused indolo[2,3‐ a ]carbazole derivatives 2 ‐ 5 are reported. The key step involved in the synthesis of triazole fused indolo[2,3‐ a ]carbazole derivatives is the Cadogan ring closing reaction. 2‐Hexyl‐5,6‐dinitro‐2 H ‐benzo[ d ][1,2,3]triazoles having 4,7‐diaryl capping were subjected to the Cadogan cyclization reaction to obtain compounds 2‐5 . In contrast to thiadiazole‐fused indolo[2,3‐ a ]carbazole 1 , bromination of triazole‐fused indolo[2,3‐ a ]carbazole 4 afforded only meta‐dibrominated product with respect to the nitrogen of fused pyrrole rings on treatment with both N ‐bromosuccinimide (NBS) and elemental bromine. These compounds showed positive solvatochromism in their emission spectra. Incorporation of electron‐donating substituent in the indole moiety resulted in the elevation of the highest occupied molecular orbital (HOMO) level. Density functional theory (DFT) calculations were performed to support the experimental findings.