A Reversible Photoacid Functioning in PBS Buffer under Visible Light

A metastable-state photoacid that can reversibly release a proton in PBS buffer (pH = 7.4) under visible light is reported. The design is based on the dual acid–base property and tautomerization of indazole. The quantum yield was as high as 0.73, and moderate light intensity (102 μmol·m2·s–1) is suf...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2015-09, Vol.137 (35), p.11282-11284
Main Authors: Abeyrathna, Nawodi, Liao, Yi
Format: Article
Language:English
Subjects:
Animals
Buffers
Hydrogen-Ion Concentration
Indazoles - chemistry
Light
Photochemical Processes
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Summary:A metastable-state photoacid that can reversibly release a proton in PBS buffer (pH = 7.4) under visible light is reported. The design is based on the dual acid–base property and tautomerization of indazole. The quantum yield was as high as 0.73, and moderate light intensity (102 μmol·m2·s–1) is sufficient for the photoreaction. Reversible pH change of 1.7 units was demonstrated using a 0.1 mM aqueous solution. This type of photoacid is promising for control of proton-transfer processes in physiological conditions and may find applications in biomedical areas.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.5b06218