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 Гру 2018
Accepted
29 Січ 2019
First published
30 Січ 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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