Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Pyridine–Spiropyran Derivative as a Persistent, Reversible Photoacid in Water

Pyridine–Spiropyran Derivative as a Persistent, Reversible Photoacid in Water
Thomas Halbritter, Josef Wachtveitl, Christoph Kaiser, Alexander Heckel
A highly versatile water-soluble pyridine–spiropyran photoswitch is reported which functions as photoacid in a wide pH range. Under neutral conditions, the open-ring merocyanine (MC–) exists to 48% and closes quantitatively by irradiation with visible light, while the reverse reaction occurs rapidly in the dark or by irradiation at 340 nm. The different pKa of the pyridine nitrogen in the closed spiropyran (4.8) and open merocyanine form (6.8) leads to a reversible proton release in a pH range of 3–7. Only negligible hydrolytic decomposition was observed in the pH range from 1 to 12. The application of potentially harmful UV light can be circumvented due to the fast thermal ring-opening except for pH values below 3. Its photoacidic properties make this compound an effective pH-regulating photoswitch in water and enable controlled proton-transfer processes for diverse applications. Additionally, all of the involved protonated states of the compound exhibit discriminative fluorescence features within certain pH ranges, which even expands its utility to a light-controllable, pH-sensitive fluorophore.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01268

DOI: 10.1021/acs.joc.7b01268

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