Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 133, Issue 37, Pages 14699-14703Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja203851c
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Funding
- Air Force Office of Scientific Research [AFOSR-(FA9550-09-1-0628)]
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A visible-light activatable photoacid has been studied, which upon irradiation, changes from a weak acid, with a pK(a) of 7.8, to a strong acid, which achieves nearly complete proton dissociation. This process is reversible and the half-life of the proton-dissociation state is similar to 70s. The long lifetime of the proton-dissociation state is due to a sequential intramolecular photochromic reaction. Using this photoacid, a pH change of 2.2 units has been achieved. In addition, we demonstrated that the photoinduced proton concentration can catalyze an esterification reaction, and greatly alter the volume of a pH-sensitive polymer. This work shows that acid-catalyzed and pH-sensitive processes can be photochemically controlled by using this type of photoacid.
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