Thiophenol detection using an AIE fluorescent probe through self-assembly with TPE-based glycoclusters

• Published in: Organic & biomolecular chemistry Vol. 17; no. 41; pp. 9251 - 9256
• Main Authors: Dong, Lei, Chen, Guo-Rong, He, Xiao-Peng, Vidal, Sébastien
• Format: Journal Article
• Language: English
• Published: CAMBRIDGE Royal Soc Chemistry 23.10.2019; Royal Society of Chemistry
• Subjects: Analytical chemistry; Aqueous solutions; Chemical Sciences; Chemistry; Chemistry, Organic; Fluorescent indicators; Hydrophobicity; Physical Sciences; Science & Technology; Selectivity; Self-assembly; Solubility; Thiophenol; Water analysis; Water sampling; TURN-ON PROBE; THIOLS; TOXICITY; SENSITIVE DETECTION; SELECTIVE DETECTION; AGGREGATION-INDUCED EMISSION
• ISSN: 1477-0520; 1477-0539; 1477-0539
• DOI: 10.1039/c9ob01937e

We describe a novel green-emitting tetraphenylethylene-dicyanomethylene-4 H -pyran (TPE-DCM) based fluorescent probe ( TD-1 ). Conjugating TPE and DCM moieties allowed TD-1 to display high selectivity for thiophenol with excellent AIE properties in aqueous solution. Nevertheless, the poor water solubility of the hydrophobic structure resulted in a weak and unstable emission intensity. The non-covalent self-assembly of TD-1 with a TPE glycocluster (TPE2S) led to a largely improved water solubility producing a reliable and stable sensing system. The corresponding glyco-probe could sensitively detect exogenous thiophenol concentrations in PBS buffer or environmental water samples. While the original probe ( TD-1 ) was not efficient enough, supramolecular self-assembly with a glycocluster ( TPE2S or TPE4S ) could restore and enhance its fluorescence detection properties.