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 (10(2) mu mol center dot m(2)center dot 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.