Boronate-Based Fluorescence Probes for the Detection of Hydrogen Peroxide
- 주제(키워드) boronic acids , diagnostics , fluorescent probes , H2O2 , intramolecular charge transfer (ICT)
- 주제(기타) Chemistry, Multidisciplinary
- 설명문(일반) [Lampard, Emma V.; Sedgwick, Adam C.; Filer, Katherine L.; Hewins, Samantha C.; Bull, Steven D.; James, Tony D.] Univ Bath, Dept Chem, Bath BA2 7AY, Avon, England; [Sun, Xiaolong] Univ Texas Austin, Dept Chem, Austin, TX 78712 USA; [Kim, Gyoungmi; Yoon, Juyoung] Ewha Womans Univ, Dept Chem & Nanosci, Seoul 120750, South Korea
- 등재 SCIE, SCOPUS
- 발행기관 WILEY-V C H VERLAG GMBH
- 발행년도 2018
- URI http://www.dcollection.net/handler/ewha/000000151525
- 본문언어 영어
- Published As http://dx.doi.org/10.1002/open.201700189
초록/요약
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 (H2O2). DSTBPin and MSTBPin displayed an "Off-On" fluorescence response towards H2O2, owing to the loss of the intramolecular charge transfer (ICT) excited state. Whereas, CSTBPin displayed a decrease in fluorescence intensity in the presence of H2O2 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 H2O2 (>3mm) to produce noticeable changes in fluorescence intensity and, therefore, no change in fluorescence was observed in the cell imaging experiments.
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