Title

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

Authors

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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