Visible-Light-Responsive Reversible Photoacid Based on a Metastable Carbanion
Abbreviated Journal Title
carbanions; photoacids; photochemistry; UV/Vis spectroscopy; STATE PROTON-TRANSFER; PHOTOINITIATED CATIONIC-POLYMERIZATION; GENERATING SYSTEMS; SALTS; DIALKYLPHENACYLSULFONIUM; DESIGN; Chemistry, Multidisciplinary
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.
Chemistry-a European Journal
"Visible-Light-Responsive Reversible Photoacid Based on a Metastable Carbanion" (2014). Faculty Bibliography 2010s. 5521.