Journal
TETRAHEDRON
Volume 71, Issue 21, Pages 3195-3202Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2015.04.012
Keywords
Imidazole/pyrene/imidazole core; N-alkylation; cis and trans Isomerism; H-1 NMR spectrum; Organic semiconductor
Categories
Funding
- Major State Basic Research Development Programs [2013CB922101, 2011CB933300]
- National Natural Science Foundation of China [21171088]
- Natural Science Foundation of Jiangsu Province [BK20130054, BE-2014147-1]
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We report the design and synthesis of three new imidazo[5,4-f]2,7-di-tert-butyl-pyrene-imidazol derivatives prepared from 2,7-di-tert-butylpyrene-4,5,9,10-tetraone and respective aromatic aldehyde through Debus-Radziszewski reaction. It is noted that three pairs of cis and trans isomers (1-6) can be separated after double imidazole N-alkylation for the central fused imidazole/pyrene/imidazole core, because of their distinguishable molecular polarity and improved solubility. Successful separation of every cis and trans isomeric pair can be verified by the single-crystal structural and spectral proofs. To the best of our knowledge, the current study is the first structural and spectral investigation on the imidazole N-alkylation of imidazole/pyrene/imidazole based compounds after successful separation of cis and trans isomers. (C) 2015 Elsevier Ltd. All rights reserved.
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