Visible-Light-Responsive Reversible Photoacid Based on a Metastable Carbanion

    Authors

    V. K. Johns; P. Peng; J. DeJesus; Z. Z. Wang;Y. Liao

    Comments

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    Abbreviated Journal Title

    Chem.-Eur. J.

    Keywords

    carbanions; photoacids; photochemistry; UV/Vis spectroscopy; STATE PROTON-TRANSFER; PHOTOINITIATED CATIONIC-POLYMERIZATION; GENERATING SYSTEMS; SALTS; DIALKYLPHENACYLSULFONIUM; DESIGN; Chemistry, Multidisciplinary

    Abstract

    A new photoacid that reversibly changes from a weak to a strong acid under visible light was designed and synthesized. Irradiation generated a metastable state with high CH acidity due to high stability of a trifluoromethyl-phenyl-tricyano-furan (CF3PhTCF) carbanion. This long-lived metastable state allows a large proton concentration to be reversibly produced with moderate light intensity. Reversible pH change of about one unit was demonstrated by using a 0.1mM solution of the photoacid in 95% ethanol. The quantum yield was calculated to be as high as 0.24. Kinetics of the reverse process can be fitted well to a second-order-rate equation with k=9.78x10(2)M(-1)s(-1). Response to visible light, high quantum yield, good reversibility, large photoinduced proton concentration under moderate light intensity, and good compatibility with organic media make this photoacid a promising material for macroscopic control of proton-transfer processes in organic systems.

    Journal Title

    Chemistry-a European Journal

    Volume

    20

    Issue/Number

    3

    Publication Date

    1-1-2014

    Document Type

    Article

    Language

    English

    First Page

    689

    Last Page

    692

    WOS Identifier

    WOS:000329481800011

    ISSN

    0947-6539

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