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Boronate-Based Fluorescence Probes for the Detection of Hydrogen Peroxide.

ChemistryOpen 2018 March
In this work, we synthesized a series of boronate ester fluorescence probes ( E )-4,4,5,5-tetramethyl-2-(4-styrylphenyl)-1,3,2-dioxaborolane ( STBPin) , ( E )- N , N -dimethyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)styryl)aniline ( DSTBPin) , ( E )-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)styryl)benzonitrile ( CSTBPin) , ( E )-2-(4-(4-methoxystyryl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane ( MSTBPin) , ( E )- N , N -dimethyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)styryl)naphthalen-1-amine ( NDSTBPin ), and N , N -dimethyl-4-(2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)oxazol-5-yl)aniline ( DAPOX-BPin ) for the detection of hydrogen peroxide (H2 O2 ). DSTBPin and MSTBPin displayed an "Off-On" fluorescence response towards H2 O2 , owing to the loss of the intramolecular charge transfer (ICT) excited state. Whereas, CSTBPin displayed a decrease in fluorescence intensity in the presence of H2 O2 owing to the introduction of an ICT excited state. STBPin , on the other hand, produced a small fluorescence decrease, indicating the importance of an electron-withdrawing or electron-donating group in these systems. Unfortunately, the longer wavelength probe, NDSTBPin , displayed a decrease in fluorescence intensity. Oxazole-based probe DAPOX-BPin produced a "turn-on" response. Regrettably, DAPOX-BPin required large concentrations of H2 O2 (>3 mm) to produce noticeable changes in fluorescence intensity and, therefore, no change in fluorescence was observed in the cell imaging experiments.

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