A Vibration‐Induced‐Emission‐Based Fluorescent Chemosensor for the Selective and Visual Recognition of Glucose

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 complexationinduced 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.

Combination of Two Colorless Fluorophores for Full-Color Red-Green-Blue Luminescence

“…Inspired by the steric hindrance-promoted larger Stokes shift of DPAC s, we revisited DHP s’ emission behaviors and excited-state processes in collaboration with Chou’s group and found that the DHP s’ molecule should encounter a bent-to-planar vibration and the reverse in the lowest excited state (S 1 ; Figure a). It has been further confirmed that the degree of the bend-to-planar vibration of DPAC s in S 1 can be trapped in fine-tuning conformations to regulate the emission peaks ranging from ∼400 to ∼610 nm, rather than tuning the intensity ratio of dual-emission bands. − This kind of emission behavior was marked as “vibration-induced emission (VIE)”, i.e., multicolor luminescences with various emission peaks (not double peaks) depending on the intrinsic conformation transition of a single molecular entity. − …”

Design strategies and applications of novel functionalized phenazine derivatives: a review

“…Besides that, Ramos-Soriano and co-workers 112 developed a novel supramolecular chemosensor 18 in 2021, which could selectively and visually recognize glucose in aqueous media. Herein, as shown in Scheme 8, this synthetic strategy involved introducing bis-2-( N -methylaminomethyl)phenylboronic acid into dihydrophenazine with the VIE effect to furnish the desired molecule 18 .…”

Synthetic strategies of phenazine derivatives: A review

“…As easy as 2012, Amanpour and co-workers [84] furnished an efficient and simple approach for the synthesis of biologically interesting phenazine derivatives (51)(52)(53)(54)(55)(56)(57)(58)(59)(60)(61)(62)(63)(64). As shown in Scheme 9, 14 highly functionalized phenazine derivatives (51)(52)(53)(54)(55)(56)(57)(58)(59)(60)(61)(62)(63)(64) were selectively achieved by the one-pot, four-component condensation reaction and were gotten good to excellent yields in the absence of any catalysts in N, N-dimethlformamide. Additionally, this approach also allowed for the synthesis of expected products due to simple and readily available precursors under neutral conditions without activation or modifications.…”

“…In sharp contrast, these synthetic strategies epitomize powerful alternatives with sustainable, facile, and highefficient principles for the formation of complex molecules, such as electrochemical strategy, biosynthesis, microwave method, supramolecular catalysis, photocatalysis, and some chemical synthesis [16,[44][45][46][47][48][49][50][51][52][53][54][55][56]. Notably, these strategies effectively avoid the major drawbacks of traditional methods and simultaneously provide concise process to furnish structurally various phenazine derivatives in good to excellent yields [49,[57][58][59][60][61][62][63].…”