| Enantioselective Recognition of Mandelic Acid by a 3,6-Dithiophen-2-yl-9H-carbazole Based Chiral Fluorescent Bisboronic Acid Sensor. | |
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MedLine Citation:
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PMID: 21619028 Owner: NLM Status: Publisher |
Abstract/OtherAbstract:
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We have prepared chiral fluorescent bisboronic acid sensors with 3,6-dithiophen-2-yl-9H-carbazole as the fluorophore. Thiophene moiety was used to extend the pi-conjugation framework of the fluorophore in order to red-shift of the fluorescence emission, and at the same time, to enhance the novel d-PET effect of the boronic acid sensors, i.e. the background fluorescence of the sensor 1 at acidic pH is weaker compared to that at neutral or basic pH, in stark contrast to the typical a-PET boronic acid sensors. The benefit of the d-PET boronic acid sensors is that the recognition of the hydroxylic acids can be achieved at acidic pH. We found that the thiophene moiety is an efficient pi-conjugation linker and electron-donor, as a result, the d-PET contrast ratio of the sensors upon variation of the pH is improved 10-fold when compared to the previously reported d-PET sensors without the thiophene moiety. Enantioselective recognition of tartaric acid was achieved at acid pH and the enantioselectivity (total response KDIFD/KLIFL) is 3.3. The fluorescence enhancement (IFSample/IFBlank) of sensor 1 upon binding with tartaric acid is 3.5-fold at pH 3.0. Unprecedented enantioselective recognition of mandelic acid was achieved with the fluorescent bisboronic acid sensor 1. To the best of our knowledge, this is the first time that the mandelic acid has been enantioselectively recognized using a chiral fluorescent boronic acid sensor. Chiral monoboronic acid sensor 2, and bisboronic acid sensor 3 without the thiophene moiety, failed to enantioselectively recognize mandelic acid. Our findings with the thiophene-incorporated boronic acid sensors will be important for the design of d-PET fluorescent sensors for the enantioselective recognition of alpha-hydroxylic acids such as mandelic acid, given that it is currently a challenge to recognize these analytes with boronic acid fluorescent molecular sensors. |
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Authors:
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Yubo Wu; Huimin Guo; Tony D James; Jianzhang Zhao |
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Publication Detail:
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Type: JOURNAL ARTICLE Date: 2011-5-27 |
Journal Detail:
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Title: The Journal of organic chemistry Volume: - ISSN: 1520-6904 ISO Abbreviation: - Publication Date: 2011 May |
Date Detail:
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Created Date: 2011-5-30 Completed Date: - Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 2985193R Medline TA: J Org Chem Country: - |
Other Details:
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Languages: ENG Pagination: - Citation Subset: - |
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