Long-Lived Photoacid Based upon a Photochromic Reaction

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 ∼70s. The long lifetime...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 133; no. 37; pp. 14699 - 14703
Main Authors Shi, Zheng, Peng, Ping, Strohecker, Daniel, Liao, Yi
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 21.09.2011
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
MECHANISM
DYNAMICS
STATE PROTON-TRANSFER
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Summary: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 ∼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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ISSN:0002-7863
1520-5126
DOI:10.1021/ja203851c