1. A triphenylamine derivative with multistimuli responsive behavior and high-contrast vapochromism of its Zn(II) complex.
- Author
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Wang, Dan, Shao, Tian-Fen, Li, Shu-Mu, Cao, Wei, Yao, Qi, and Ma, Yangmin
- Subjects
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TRIPHENYLAMINE , *ELEMENTAL analysis , *INFRARED spectroscopy , *EXCITED states , *DETECTION limit , *PROTON transfer reactions - Abstract
In this work, we designed and synthesized a novel multifunctional molecule, (E)-2-(4-(diphenylamino)styryl)-5-(4-pyridyl)-8-quinolinol (HL), which possessed D-π-A structure and exhibited optical responses to acid-base vapor and Zn(II) ions. Zn(II) complex of HL (W1) was obtained and characterized by SC-XRD. Spectral experiments demonstrated that complex W1 displayed aggregation-induced emission enhancement (AIEE) property, which was exact opposite to the aggregation-caused quenching effect of HL. The quantum yield of W1 (15%) was much higher than that of HL (2.1%) in the solid state. Both HL and complex W1 involved sp2 hybrid N atoms, whose protonation and deprotonation gave rise to reversible acidochromism with high contrast. The mechanism was clarified by XPS, 1H NMR, infrared spectroscopy, elemental analysis, PXRD and thermogravimetry results. Benefiting from excited state intramolecular proton transfer in HL together with AIEE of W1 , HL could recognize Zn(II) sensitively in aqueous media. The detection limit of HL for Zn(II) reached as low as 5.02 × 10−8 M. An anti-counterfeiting application was realized using HL -loaded test strip, which exhibited fluorescence response, but no color change upon exposure to Zn(II) solution. In addition, HL and W1 solids were combined to develop a stimuli induced encryption/decryption strategy successfully based on their reversible acidochromic behaviors. [Display omitted] • A triphenylamine derivative with D-π-A structure was synthesized and displayed multistimuli photoresponsive behavior. • Its Zn(II) complex exhibited AIE and reversible acidochromism characters. • The mechanisms for these photoresponsive behaviors were clarified via a series of experiments. • Test strip and information encryption/decryption applications were realized based on these stimuli-responsive properties. [ABSTRACT FROM AUTHOR]
- Published
- 2024
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