Tetraphenylethene functionalized quinoxaline derivative exhibiting aggregation-induced emission and multi-stimuli responsive fluorescent switching

A new tetraphenylethene functionalized quinoxaline derivative TPVSQ has been synthesized using classical Knoevenagel condensation reaction. Spectral study and quantum chemical calculation indicated that it possessed D-π-A molecular structure. TPVSQ exhibited typical ICT (intramolecular charge transf...

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Bibliographic Details
Published in:Tetrahedron 2022-01, Vol.104, p.132600, Article 132600
Main Authors: Xiang, Xiuyin, Zhan, Yong, Yang, Wenjun
Format: Article
Language:English
Subjects:
Aggregationinduced emission
Intramolecular charge transfer
Mechanochromism
Multi-stimuli response
Tetraphenylethene
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Summary:A new tetraphenylethene functionalized quinoxaline derivative TPVSQ has been synthesized using classical Knoevenagel condensation reaction. Spectral study and quantum chemical calculation indicated that it possessed D-π-A molecular structure. TPVSQ exhibited typical ICT (intramolecular charge transfer) transition and AIE property. Interestingly, TPVSQ also showed multi-stimuli responsive behavior. The emission spectra of TPVSQ could be switched in response to not only mechanical grinding and solvent fuming but also the protonation effect. The responsive mechanism has been studied and explained. The current work provided a strategy for the molecular design of new multi-stimuli responsive materials. [Display omitted] •A new tetraphenylethene functionalized quinoxaline derivative TPVSQ has been prepared.•It should be noted that TPVSQ showed ICT and AIE characteristics.•TPVSQ exhibited a clear response to acid in both solution and solid state.
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2021.132600