First fluorescent sensor for curcumin in aqueous media based on acylhydrazone-bridged bis-tetraphenylethylene

Shengjie Jiang; Jiabin Qiu; Bingni Lin; Hongyu Guo; Fafu Yang

doi:10.1016/j.saa.2019.117916

First fluorescent sensor for curcumin in aqueous media based on acylhydrazone-bridged bis-tetraphenylethylene

Spectrochim Acta A Mol Biomol Spectrosc. 2020 Mar 15:229:117916. doi: 10.1016/j.saa.2019.117916. Epub 2019 Dec 9.

Authors

Shengjie Jiang¹, Jiabin Qiu¹, Bingni Lin¹, Hongyu Guo², Fafu Yang³

Affiliations

¹ College of Chemistry and Materials, Fujian Normal University, Fuzhou 350007, PR China1.
² College of Chemistry and Materials, Fujian Normal University, Fuzhou 350007, PR China1; Fujian Key Laboratory of Polymer Materials, Fuzhou 350007, PR China.
³ College of Chemistry and Materials, Fujian Normal University, Fuzhou 350007, PR China1; Fujian provincial Key Laboratory of Advanced Materials Oriented Chemical Engineering, Fuzhou 350007, PR China. Electronic address: yangfafu@fjnu.edu.cn.

PMID: 31839575
DOI: 10.1016/j.saa.2019.117916

Abstract

This work designed and synthesized the first organic fluorescent sensor for curcumin in aqueous media based on red-to-green fluorescence change of acylhydrazone-bridged bis-tetraphenylethylene (Bis-TPE). Bis-TPE was prepared by condensation of formyltetraphenylethylene with dihydrazide oxalate in 86% yield. It has the large conjugated electron effect with strong red AIE fluorescence in aqueous solution. It displayed high selective sensing ability for curcumin with red-to-green fluorescence change in THF-H₂O (5:95). The detection limit was as low as 1.15 × 10^-⁷ M. The sensing mechanism was confirmed as 1:1 stoichiometric ratio based on quadruple hydrogen bonds. Bis-TPE was successfully applied for analyzing curcumin of ginger and living cell imaging, supplying a new detecting strategy for curcumin in real sample and living environment.

Keywords: Aqueous media; Curcumin; Fluorescence; Sensor; Tetraphenylethylene.

MeSH terms

Curcumin / analysis*
Fluorescent Dyes* / chemical synthesis
Fluorescent Dyes* / chemistry
Limit of Detection
Spectrometry, Fluorescence
Stilbenes / chemistry*
Water / chemistry

Substances

Fluorescent Dyes
Stilbenes
tetraphenylethylene
Water
Curcumin