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Bistable Aryl Azopyrazolium Ionic Photoswitches in Water

Ankit Kumar Gaur, Debapriya Gupta, Anjali Mahadevan, Pravesh Kumar, Himanshu Kumar, Dhanyaj Narayanan Nampoothiry, Navneet Kaur, Sandeep Kumar Thakur, Sanjay Singh, Tomáš Slanina, Sugumar Venkataramani

2023Journal of the American Chemical Society38 citationsDOI

Abstract

We report a new class of arylazopyrazolium-based ionic photoswitches (AAPIPs). These AAPIPs with different counter ions have been accessed through a modular synthetic approach in high yields. More importantly, the AAPIPs exhibit excellent reversible photoswitching and exceptional thermal stability in water. The effects of solvents, counter ions, substitutions, concentration, pH, and glutathione (GSH) have been evaluated using spectroscopic investigations. The results revealed that the bistability of studied AAPIPs is robust and near quantitative. The thermal half-life of Z isomers is extremely high in water (up to years), and it can be lowered electronically by the electron-withdrawing groups or highly basic pH.

Topics & Concepts

ChemistryBistabilityIonic bondingIonThermal stabilityCombinatorial chemistryArylThermalPhotochemistryChemical physicsOrganic chemistryThermodynamicsOptoelectronicsPhysicsAlkylPhotochromic and Fluorescence ChemistryPhotoreceptor and optogenetics researchPorphyrin and Phthalocyanine Chemistry
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