Abstract
The development of chemosensors to detect analytes in biologically relevant solutions is a challenging task. We report the synthesis of a fluorescent receptor that combines vibration‐induced emission (VIE) and dynamic covalent chemistry for the detection of glucose in aqueous media. We show that the bis‐2‐(N‐methylaminomethyl)phenylboronic acid‐decorated N,N′‐diphenyl‐dihydrodibenzo[a,c]phenazine (DPAC) receptor 1 can detect glucose and discriminate between closely related monosaccharides including those commonly found in blood. Preliminary studies suggest monosaccharides bind to the DPAC‐receptor with a 1:1 stoichiometry to produce pseudomacrocyclic complexes, which in turn leads to distinct optical changes in the fluorescent emission of the receptor for each host. Moreover, the complexation‐induced change in emission can be detected visually and quantified in a ratiometric way. Our results highlight the potential of VIE‐type receptors for the quantitative determination of saccharides in biological samples.
Highlights
The development of chemosensors to detect analytes in biologically relevant solutions is a challenging task
Among the different glucose sensors reported so far, phenylboronic acid-based molecules, which are known for their ability to form reversible covalent bonds with 1,2-diols in aqueous media are one of the most studied.[6]
We present a new fluorescent monosaccharide receptor that operates in aqueous media, which features a vibration-induced emission (VIE) signalling unit tethered via aminomethyl moieties to two phenylboronic acid motifs able to form dynamic covalent bonds with 1,2-diols
Summary
The development of chemosensors to detect analytes in biologically relevant solutions is a challenging task. In the case of glucose, the recognition process gives rise to the most drastic change both in colour and increased fluorescence intensity, even in the presence of other monosaccharides.
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