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A–π–D–π–A carbazole derivatives with remarkable solvatochromism and mechanoreponsive luminescence turn-on

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Abstract

Two A–π–D–π–A molecules with a carbazole donor and a dicyanovinyl acceptor but differing in N-hexyl (h-CPDM) and N-isooctyl substituents (i-CPDM) were synthesized, and both of them presented remarkable dual properties of solvatochromism and mechanoresponsive luminescence (MRL) turn-on. The intrinsic intramolecular charge transfer (ICT) characteristic endowed both luminophors with a prominent solvatochromic effect, with emission color tuning from blue to orange-red by changing the solvent from nonpolar hexane to polar dimethyl sulfoxide. Meanwhile, the non-/weakly emissive original powders of h-CPDM and i-CPDM gave bright orange (610 nm) and yellow (596 nm) emission with the photoluminescence quantum yields increasing as high as 85-fold after being ground. Investigations revealed this mechanoresponsive luminescence turn-on could be ascribed to the disturbance of the π–π stacking interactions in the non-/weakly emissive J-aggregates by mechanical force. This work offers carbazole derivatives that can be used as sensitive fluorescent indicators for organic solvents and mechanical sensors.

Graphical abstract: A–π–D–π–A carbazole derivatives with remarkable solvatochromism and mechanoreponsive luminescence turn-on

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Publication details

The article was received on 05 Feb 2017, accepted on 15 Apr 2017 and first published on 28 Apr 2017


Article type: Paper
DOI: 10.1039/C7TC00559H
Citation: J. Mater. Chem. C, 2017, Advance Article
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    A–π–D–π–A carbazole derivatives with remarkable solvatochromism and mechanoreponsive luminescence turn-on

    P. Wen, Z. Gao, R. Zhang, A. Li, F. Zhang, J. Li, J. Xie, Y. Wu, M. Wu and K. Guo, J. Mater. Chem. C, 2017, Advance Article , DOI: 10.1039/C7TC00559H

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