Controlling reactivity by remote protonation of a basic side group in a bifunctional photoacid

Literature Information

Publication Date 2015-12-18
DOI 10.1039/C5CP07672B
Impact Factor 3.676
Authors

Julia Ditkovich, Dina Pines, Ehud Pines


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Abstract

6-Hydroxy-2-naphthoic acid and its sulfonate derivatives belong to a family of bifunctional photoacids where the –OH group acts as a proton donor and the –COO− group acts as a proton acceptor. Upon electronic excitation, the –OH group becomes more acidic and the –COO− group turns more basic. Change in the ionization state of one functional group causes a change (switch) in the reactivity of the other functional group. Using picosecond time-resolved and steady state spectroscopy, we find clear evidence for an ultrafast reactivity switch caused by a diffusional proton transfer through the water solvent between the two functional groups with no evidence of a concerted proton transfer.

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Source Journal

Physical Chemistry Chemical Physics

Physical Chemistry Chemical Physics
CiteScore: 5.5
Self-citation Rate: 10.3%
Articles per Year: 3036

Physical Chemistry Chemical Physics (PCCP) is an international journal co-owned by 19 physical chemistry and physics societies from around the world. This journal publishes original, cutting-edge research in physical chemistry, chemical physics and biophysical chemistry. To be suitable for publication in PCCP, articles must include significant innovation and/or insight into physical chemistry; this is the most important criterion that reviewers and Editors will judge against when evaluating submissions. The journal has a broad scope and welcomes contributions spanning experiment, theory, computation and data science. Topical coverage includes spectroscopy, dynamics, kinetics, statistical mechanics, thermodynamics, electrochemistry, catalysis, surface science, quantum mechanics, quantum computing and machine learning. Interdisciplinary research areas such as polymers and soft matter, materials, nanoscience, energy, surfaces/interfaces, and biophysical chemistry are welcomed if they demonstrate significant innovation and/or insight into physical chemistry. Joined experimental/theoretical studies are particularly appreciated when complementary and based on up-to-date approaches.

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