Metastable photoacids (mPAHs) have the potential to regulate pH driven processes in chemical, material, and biological applications with a high degree of spatial and temporal control. Given their molecular structure (zwitterionic, planar conjugation) their utility has largely been limited to polar protic media. Expanding the scope of chemical transformations or materials is limited by the inability to be solubilized in organic media. To address these limitations, a new merocyanine based mPAH was synthesized employing simple structural modification, through commercially available starting materials. This new derivative is able to be readily solubilized in a wider range of organic solvents and with higher concentrations than previously attainable. Furthermore, the simple structural modifications, not only retained the photoswitching ability, but significantly improved the thermal relaxation, imparting an increased handle in temporal control of the acidic nature of the photoacid.

Expanding the scope of metastable photoacids into material applications

2019 Spring National Meeting

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