Issue 4, 2019

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

Abstract

In this study, we report a newly synthesized molecule 1via 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

Supplementary files

Article information

Article type
Research Article
Submitted
10 12 2018
Accepted
29 1 2019
First published
30 1 2019

Mater. Chem. Front., 2019,3, 620-625

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, 3, 620 DOI: 10.1039/C8QM00633D

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