Volume 2, 2023

Tetraphenylethene-capped aminobenzopyranoxanthene hydrazone probes for colorimetric recognition of Hg2+ and fluorescent sensing of HCl gas

Abstract

Two sensing molecules, A-T1 and A-T2 with bichromophore were synthesized by linking different numbers of TPE units to a xanthene platform (ABPX). There was a big difference in symmetry and sensing features between the two molecules. The asymmetric molecule A-T1 has hydrazide and TPE-capped hydrazone ligands, while the symmetric molecule A-T2 with two TPE units showed brighter AIE fluorescence in solid state and aqueous solution. In heavy metal ion analysis, A-T1 showed obvious absorption increase centered at 499 and 533 nm in the presence of Hg2+, and the color changed to pink; A-T2 showed weak response to Cu2+ due to the steric hindrance of TPE. The Job's Plot and ESI-MS results indicated that a 1 : 1 ligand–metal complex was formed between the A-T1 hydrazide site and Hg2+, and Cu2+ can coordinate with the TPE-capped hydrazone site. Furthermore, A-T1 powder could respond to HCl gas via the spiro-opening process, and this can be restored by NH3. The 1H NMR chemical shifts of the xanthene at 6.16 to 6.56 ppm vanished and reappeared, demonstrating the protonation of diethylamine groups by HCl gas. These probes could be applied as fluorescence indicators in vivo imaging with high resolution.

Graphical abstract: Tetraphenylethene-capped aminobenzopyranoxanthene hydrazone probes for colorimetric recognition of Hg2+ and fluorescent sensing of HCl gas

Supplementary files

Article information

Article type
Paper
Submitted
27 Feb 2023
Accepted
19 Apr 2023
First published
16 May 2023
This article is Open Access
Creative Commons BY license

Sens. Diagn., 2023,2, 842-850

Tetraphenylethene-capped aminobenzopyranoxanthene hydrazone probes for colorimetric recognition of Hg2+ and fluorescent sensing of HCl gas

Y. Yang, C. Pei, C. Gao and J. Liu, Sens. Diagn., 2023, 2, 842 DOI: 10.1039/D3SD00048F

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