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An ESIPT-based fluorescent switch with AIEE, solvatochromism, mechanochromism and photochromism

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Abstract

In this study, we report a newly synthesized molecule 1 via linking a benzothiazole to rhodamine, which could exhibit AIEE, unique acidichromism and solvatochromism in solution, fascinating photochromism in a polymer matrix, intriguing mechanochromism in solid state and remarkable piezochromism in the crystal. 1 is a rarely reported organic molecule, which is sensitive to multiple stimuli such as acid/base, force, pressure, light and solvent polarity due to its distinct intramolecular hydrogen bonding and spiro-lactam structure. 1 demonstrated AIEE property in a THF/H2O system because of the water-induced aggregation and aggregation-suppressed nonradiative relaxation of the excited states. In the solution, 1 afforded yellowish-green emission at 520 nm (keto emission) in a non-polar solvent and blue emission at 447 nm (enol emission) in a polar solvent. Surprisingly, a blue shift in the emission peak was observed in a DCM solution upon treatment with acid or base, which is quite different from that of traditional rhodamine. In the solid state, the emission color of 1 changed from yellowish-green to red upon grinding or applying hydrostatic pressure, owing to the force-induced ring-opening reaction. In the polymer matrix, 1 manifested reversible photochromic behaviour and could serve as a good photoprinting material. This study is expected to contribute to the development of multistimuli-responsive fluorescent switch with multiple functions in different states.

Graphical abstract: An ESIPT-based fluorescent switch with AIEE, solvatochromism, mechanochromism and photochromism

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Publication details

The article was received on 10 Dec 2018, accepted on 29 Jan 2019 and first published on 30 Jan 2019


Article type: Research Article
DOI: 10.1039/C8QM00633D
Citation: Mater. Chem. Front., 2019, Advance Article

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    An ESIPT-based fluorescent switch with AIEE, solvatochromism, mechanochromism and photochromism

    X. Liu, A. Li, W. Xu, Z. Ma and X. Jia, Mater. Chem. Front., 2019, Advance Article , DOI: 10.1039/C8QM00633D

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