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Substituent effects in solid-state assembly of activated benzotriazoles

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Abstract

Aromatic donor–acceptor stacking involving electron-rich π-donors and electron-deficient π-acceptors has been utilized in a broad spectrum of diverse applications to great effect. We report the discovery of unprecedented donor–acceptor stacking from a non-mixed activated benzotriazole scaffold to give cofacial π-stacking in 2D sheets. We further report the effects of altering the substituents of the bicyclic aromatic system. It was found that any alteration made to the substituents disrupted the cofacial stacking, however, both aromatic donor–acceptor stacking and 2D sheet formation was observed in the solid-state assembly of the analogues. Furthermore, interactions that satisfied both electrostatic and direct-substituent π-stacking models were observed.

Graphical abstract: Substituent effects in solid-state assembly of activated benzotriazoles

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Publication details

The article was received on 15 Oct 2018, accepted on 19 Dec 2018 and first published on 21 Dec 2018


Article type: Paper
DOI: 10.1039/C8CE01757C
Citation: CrystEngComm, 2019, Advance Article
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    Substituent effects in solid-state assembly of activated benzotriazoles

    D. S. Wenholz, M. Bhadbhade, H. Kandemir, J. Ho, N. Kumar and D. StC. Black, CrystEngComm, 2019, Advance Article , DOI: 10.1039/C8CE01757C

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