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Issue 39, 2016
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Multi-stimuli response of a novel half-cut cruciform and its application as a security ink

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Abstract

(E)-2′-[2-(Benzo[d]thiazol-2-yl)vinyl]-N,N-dimethyl-(1,1′-biphenyl)-4-amine 2, a novel V-shaped molecule (i.e. a half-cut cruciform), and its line-shaped isomer, (E)-4′-[2-(benzo[d]thiazol-2-yl)vinyl]-N,N-dimethyl-[1,1′-biphenyl]-4-amine 4, were successfully prepared via a two-step route of Suzuki coupling and Witting reaction. The much more profound ICT effect on 2 than on 4 means that the former has largely reduced quantum yields in highly polar solvents, in which AIE effect is enhanced for 2 but not for 4. Morphology-dependent fluorochromism in highly contrasted colours induced by mechanical force or surrounding pH stimuli can reversibly occur on 2 but not on 4. X-ray crystallography revealed loose molecular packing caused by the twisted conformation of 2, which is assumed to account for the intense solid-state emission and mechano-chromic activity. An organic solution of 2 and CF3COOH mixture shows potential for use as a security ink without the need for a covering reagent.

Graphical abstract: Multi-stimuli response of a novel half-cut cruciform and its application as a security ink

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Article information


Submitted
24 Jun 2016
Accepted
14 Sep 2016
First published
15 Sep 2016

J. Mater. Chem. C, 2016,4, 9350-9358
Article type
Paper

Multi-stimuli response of a novel half-cut cruciform and its application as a security ink

X. Lu and M. Xia, J. Mater. Chem. C, 2016, 4, 9350
DOI: 10.1039/C6TC02618D

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