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A new approach to thiazoloisoindigo and derivatives using a lithium tetramethylpiperidine promoted cyclization to thiazoloisatin

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Abstract

Brominated thiazoloisoindigo was synthesized for the first time from thiazoloisatin, which was obtained via an unprecedented nucleophilic cyclization strategy. Thiazoloisoindigo was shown to exhibit a deeper LUMO energy level than isoindigo and thienoisoindigo, which makes it a potential building block for n-type semiconductors. Moreover, brominated thiazoloisoindigo is sensitive toward nucleophilic attack, and its reaction with aniline resulted in an unexpectedly much more stable acceptor with a LUMO energy level as low as −3.82 eV.

Graphical abstract: A new approach to thiazoloisoindigo and derivatives using a lithium tetramethylpiperidine promoted cyclization to thiazoloisatin

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Publication details

The article was received on 15 Sep 2017, accepted on 19 Oct 2017 and first published on 23 Oct 2017


Article type: Research Article
DOI: 10.1039/C7QO00841D
Citation: Org. Chem. Front., 2018, Advance Article
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    A new approach to thiazoloisoindigo and derivatives using a lithium tetramethylpiperidine promoted cyclization to thiazoloisatin

    C. Li, H. Zhang, S. Mirie, J. Peng, M. Cai, X. Wang, Z. Lan and X. Wan, Org. Chem. Front., 2018, Advance Article , DOI: 10.1039/C7QO00841D

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