A one-pot telescopic synthesis of benzo[]carbazoles and exploration of their liquid crystalline properties

We describe a diversity-oriented one-pot telescopic synthesis of various benzo[ b ]carbazoles with the naphthannulation of indoles as the key step, enabled by an intramolecular furan-olefin Diels-Alder reaction. This strategy is general and efficient across a wide range of substrates. We applied thi...

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Bibliographic Details
Published inChemical communications (Cambridge, England) Vol. 6; no. 36; pp. 4797 - 48
Main Authors Malik, Nirmal, De, Ritobrata, Pal, Santanu Kumar, Ramasastry, S. S. V
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 30.04.2024
Royal Society of Chemistry
Subjects
Carbazoles
Chemistry
Chemistry, Multidisciplinary
Diels-Alder reactions
Indoles
Liquid crystals
Physical Sciences
Room temperature
Science & Technology
Substrates
Synthesis
BIOLOGICAL EVALUATION
CYCLIZATION
ACID
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Summary:We describe a diversity-oriented one-pot telescopic synthesis of various benzo[ b ]carbazoles with the naphthannulation of indoles as the key step, enabled by an intramolecular furan-olefin Diels-Alder reaction. This strategy is general and efficient across a wide range of substrates. We applied this method to synthesize and characterize the first benzo[ b ]carbazole-based liquid crystalline materials, where the unique molecular design led to the formation of a rare nematic phase at room temperature. A one-pot multistep strategy has been developed to synthesize benzo[ b ]carbazoles. We have applied this method to access the first benzo[ b ]carbazole-based room temperature nematic liquid crystalline materials.
Bibliography:2322120
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For ESI and crystallographic data in CIF or other electronic format see DOI
8b
Electronic supplementary information (ESI) available: Experimental details and characterisation data for new compounds. CCDC
https://doi.org/10.1039/d4cc00721b
ObjectType-Article-1
SourceType-Scholarly Journals-1
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content type line 23
ISSN:1359-7345
1364-548X
DOI:10.1039/d4cc00721b