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Boronate-Based Fluorescence Probes for the Detection of Hydrogen Peroxide
- Title
- Boronate-Based Fluorescence Probes for the Detection of Hydrogen Peroxide
- Authors
- Lampard, Emma V.; Sedgwick, Adam C.; Sun, Xiaolong; Filer, Katherine L.; Hewins, Samantha C.; Kim, Gyoungmi; Yoon, Juyoung; Bull, Steven D.; James, Tony D.
- Ewha Authors
- 윤주영
- SCOPUS Author ID
- 윤주영
- Issue Date
- 2018
- Journal Title
- CHEMISTRYOPEN
- ISSN
- 2191-1363
- Citation
- CHEMISTRYOPEN vol. 7, no. 3, pp. 262 - 265
- Keywords
- boronic acids; diagnostics; fluorescent probes; H2O2; intramolecular charge transfer (ICT)
- Publisher
- WILEY-V C H VERLAG GMBH
- Indexed
- SCIE; SCOPUS
- Document Type
- Article
- Abstract
- 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.
- DOI
- 10.1002/open.201700189
- Appears in Collections:
- 자연과학대학 > 화학·나노과학전공 > Journal papers
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