Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 60, Issue 45, Pages 24124-24130Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202107373
Keywords
aromatic bowls; carbazoles; organic semiconductors; polycyclic aromatic compounds; Scholl reaction
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Funding
- Croucher Senior Research Fellowship [SRF19402]
- Research Matching Grant from the University Grants Committee (Hong Kong)
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The synthesis of new carbazole-fused polycyclic aromatics with interesting geometry and useful properties was explored using Scholl reactions. The oxidative coupling of carbazole units occurred in a regioselective manner, forming new carbon-carbon bonds preferably at C3 and C4 in N-alkyl carbazoles. A new N-containing aromatic bowl was characterized, and new p-type organic semiconductors exhibited field effect mobility of up to 0.070 cm(2) V-1 s(-1) in solution-processed thin-film transistors.
The synthesis of new carbazole-fused polycyclic aromatics with interesting geometry and useful properties was explored using Scholl reactions. As found from the Scholl reactions of substrates having two carbazole units linked at different positions through o-phenylene, oxidative coupling of carbazole units occurred in a regioselective manner with new carbon-carbon bonds preferably formed at C3 and C4 in N-alkyl carbazoles. A new N-containing aromatic bowl was characterized by single-crystal X-ray crystallography, and new p-type organic semiconductors exhibited field effect mobility of up to 0.070 cm(2) V-1 s(-1) in solution-processed thin-film transistors.
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