Quantification of Excited-State Brønsted–Lowry Acidity of Weak Photoacids Using Steady-State Photoluminescence Spectroscopy and a Driving-Force-Dependent Kinetic Theory

Bhide, Rohit; Feltenberger, Cassidy N.; Phun, Gabriel S.; Barton, Grant; Fishman, Dmitry; Ardo, Shane

doi:10.1021/jacs.2c00554

Quantification of Excited-State Brønsted–Lowry Acidity of Weak Photoacids Using Steady-State Photoluminescence Spectroscopy and a Driving-Force-Dependent Kinetic Theory

Journal Article · 02 August 2022 · Journal of the American Chemical Society

DOI:https://doi.org/10.1021/jacs.2c00554· OSTI ID:1978466

Bhide, Rohit ^[1]; Feltenberger, Cassidy N. ^[2]; Phun, Gabriel S. ^[2]; Barton, Grant ^[2]; ^[3]; ^[4]

Department of Chemistry, University of California─Irvine, Irvine, California 92697, United States; OSTI
Department of Chemistry, University of California─Irvine, Irvine, California 92697, United States
Department of Chemistry, University of California─Irvine, Irvine, California 92697, United States; Laser Spectroscopy Laboratories, University of California─Irvine, Irvine, California 92697, United States
Department of Chemistry, University of California─Irvine, Irvine, California 92697, United States; Department of Chemical & Biomolecular Engineering, University of California─Irvine, Irvine, California 92697, United States; Department of Materials Science & Engineering, University of California─Irvine, Irvine, California 92697, United States

Not provided.

Research Organization:: Univ. of California, Irvine, CA (United States)

Sponsoring Organization:: USDOE Office of Science (SC)

DOE Contract Number:: SC0019162;

OSTI ID:: 1978466

Journal Information:: Journal of the American Chemical Society, Journal Name: Journal of the American Chemical Society Journal Issue: 32 Vol. 144; ISSN 0002-7863

Publisher:: American Chemical Society (ACS)

Country of Publication:: United States

Language:: English

References (77)

Light‐Driven Active Proton Transport through Photoacid‐ and Photobase‐Doped Janus Graphene Oxide Membranes Wang, Lili; Wen, Qi; Jia, Pan Advanced Materials, Vol. 31, Issue 36 https://doi.org/10.1002/adma.201903029	journal	June 2019
Proton Transfer, Acid-Base Catalysis, and Enzymatic Hydrolysis. Part I: ELEMENTARY PROCESSES Eigen, M. Angewandte Chemie International Edition in English, Vol. 3, Issue 1 https://doi.org/10.1002/anie.196400011	journal	January 1964
Recent Advances and Challenges in the Design of Organic Photoacid and Photobase Generators for Polymerizations Zivic, Nicolas; Kuroishi, Paula K.; Dumur, Frédéric Angewandte Chemie International Edition, Vol. 58, Issue 31 https://doi.org/10.1002/anie.201810118	journal	April 2019
In‐Operando Mapping of pH Distribution in Electrochemical Processes Fuladpanjeh‐Hojaghan, Behzad; Elsutohy, Mohamed M.; Kabanov, Vladimir Angewandte Chemie International Edition, Vol. 58, Issue 47 https://doi.org/10.1002/anie.201909238	journal	November 2019
Die p_H‐Abhängigkeit der Fluoreszenz von Naphthalinderivaten Förster, Th. Zeitschrift für Elektrochemie und angewandte physikalische Chemie, Vol. 54, Issue 7 https://doi.org/10.1002/bbpc.19500540707	journal	December 1950
Allgemeine Basenkatalyse bei der elektrolytischen Dissoziation angeregter Naphthole Weller, Albert Zeitschrift für Elektrochemie, Berichte der Bunsengesellschaft für physikalische Chemie, Vol. 58, Issue 10 https://doi.org/10.1002/bbpc.19540581006	journal	January 1954
Protolytische Reaktionen des angeregten Acridins Weller, Albert Zeitschrift für Elektrochemie, Berichte der Bunsengesellschaft für physikalische Chemie, Vol. 61, Issue 8 https://doi.org/10.1002/bbpc.19570610818	journal	October 1957
Photoactivation of an Acid-Sensitive Ion Channel Associated with Vision and Pain Shafaat, Oliver S.; Winkler, Jay R.; Gray, Harry B. ChemBioChem, Vol. 17, Issue 14 https://doi.org/10.1002/cbic.201600230	journal	June 2016
Kinetics of Fluorescence Quenching by Electron and H-Atom Transfer Rehm, Dieter; Weller, Albert Israel Journal of Chemistry, Vol. 8, Issue 2 https://doi.org/10.1002/ijch.197000029	journal	January 1970
From energy profiles to structure-reactivity correlations Agmon, N. International Journal of Chemical Kinetics, Vol. 13, Issue 4 https://doi.org/10.1002/kin.550130403	journal	April 1981
Theory of Electron Transfer Reactions and Comparison with Experiments Marcus, R. A.; Siddarth, Prabha Photoprocesses in Transition Metal Complexes, Biosystems and Other Molecules. Experiment and Theory https://doi.org/10.1007/978-94-011-2698-4_2	book	January 1992
Fluoreszenzspektrum und Wasserstoffionen-konzentration F�rster, Th. Die Naturwissenschaften, Vol. 36, Issue 6 https://doi.org/10.1007/BF00626582	journal	January 1949
Phosphate diffusion in soil and uptake by plants: I. Self-diffusion of phosphate in soils Lewis, D. G.; Quirk, J. P. Plant and Soil, Vol. 26, Issue 1 https://doi.org/10.1007/BF01978678	journal	February 1967
Kinetics of proton transfer reactions involving hydroxypyrene-trisulphonate in aqueous solution by nanosecond laser absorption spectroscopy Förster, Th.; Völker, S. Chemical Physics Letters, Vol. 34, Issue 1 https://doi.org/10.1016/0009-2614(75)80188-6	journal	July 1975
Energy, entropy and the reaction coordinate: thermodynamic-like relations in chemical kinetics Agmon, N.; Levine, R. D. Chemical Physics Letters, Vol. 52, Issue 2 https://doi.org/10.1016/0009-2614(77)80523-X	journal	December 1977
Excited state proton transfer reactions of acridine studied by nanosecond fluorometry Gafni, Ari; Brand, Ludwig Chemical Physics Letters, Vol. 58, Issue 3 https://doi.org/10.1016/0009-2614(78)85050-7	journal	October 1978
Equilibrium pK* of carbazole studied by the deprotonation reaction in ammoniacal aqueous media Chattopadhyay, Nitin; Chowdhury, Mihir Journal of Photochemistry, Vol. 38 https://doi.org/10.1016/0047-2670(87)87025-9	journal	June 1987
Excited state deprotonation reactions of aromatic amines: a diffusion-controlled process Chattopadhyay, Nitin; Samanta, Anunay; Kundu, Tapanendu Journal of Photochemistry and Photobiology A: Chemistry, Vol. 48, Issue 1 https://doi.org/10.1016/1010-6030(89)87090-X	journal	July 1989
Excited-state proton transfer reactions I. Fundamentals and intermolecular reactions Arnaut, Luís G.; Formosinho, Sebastião J. Journal of Photochemistry and Photobiology A: Chemistry, Vol. 75, Issue 1 https://doi.org/10.1016/1010-6030(93)80157-5	journal	October 1993
Determination of in excited state proton transfer (ESPT) reaction: a rearrangement of Weller's equation; advantage of dual luminescence Chattopadhyay, Nitin Journal of Photochemistry and Photobiology A: Chemistry, Vol. 88, Issue 1 https://doi.org/10.1016/1010-6030(94)03992-4	journal	May 1995
Direct measurement of intrinsic proton transfer rates in diffusion-controlled reactions Pines, Ehud; Magnes, Ben-Zion; Lang, Matthew J. Chemical Physics Letters, Vol. 281, Issue 4-6 https://doi.org/10.1016/S0009-2614(97)01245-1	journal	December 1997
Excited-state acid–base chemistry of coordination complexes Hicks, Charles; Ye, Guozhong; Levi, Chaim Coordination Chemistry Reviews, Vol. 211, Issue 1 https://doi.org/10.1016/S0010-8545(00)00279-4	journal	January 2001
Aqueous bimolecular proton transfer in acid–base neutralization Mohammed, Omar F.; Pines, Dina; Pines, Ehud Chemical Physics, Vol. 341, Issue 1-3 https://doi.org/10.1016/j.chemphys.2007.06.040	journal	November 2007
Conversion of Visible Light into Ionic Power Using Photoacid-Dye-Sensitized Bipolar Ion-Exchange Membranes White, William; Sanborn, Christopher D.; Fabian, David M. Joule, Vol. 2, Issue 1 https://doi.org/10.1016/j.joule.2017.10.015	journal	January 2018
Turning water into a protonic diode and solar cell via doping and dye sensitization Schulte, Leanna; White, William; Renna, Lawrence A. Joule https://doi.org/10.1016/j.joule.2021.06.016	journal	July 2021
How Acidic Is Carbonic Acid? Pines, Dina; Ditkovich, Julia; Mukra, Tzach The Journal of Physical Chemistry B, Vol. 120, Issue 9 https://doi.org/10.1021/acs.jpcb.5b12428	journal	February 2016
Controlling Proton Conductivity with Light: A Scheme Based on Photoacid Doping of Materials Haghighat, Shima; Ostresh, Sarah; Dawlaty, Jahan M. The Journal of Physical Chemistry B, Vol. 120, Issue 5 https://doi.org/10.1021/acs.jpcb.6b00370	journal	January 2016
Operando Local pH Measurement within Gas Diffusion Electrodes Performing Electrochemical Carbon Dioxide Reduction Welch, Alex J.; Fenwick, Aidan Q.; Böhme, Annette The Journal of Physical Chemistry C, Vol. 125, Issue 38 https://doi.org/10.1021/acs.jpcc.1c06265	journal	September 2021
Electrochemically Induced pH Change: Time-Resolved Confocal Fluorescence Microscopy Measurements and Comparison with Numerical Model Pande, Nakul; Chandrasekar, Shri K.; Lohse, Detlef The Journal of Physical Chemistry Letters, Vol. 11, Issue 17 https://doi.org/10.1021/acs.jpclett.0c01575	journal	July 2020
Excited-state proton-transfer reactions and proton-induced quenching of aromatic compounds Shizuka, Haruo Accounts of Chemical Research, Vol. 18, Issue 5 https://doi.org/10.1021/ar00113a003	journal	May 1985
Excited-State Proton Transfer: From Constrained Systems to “Super” Photoacids to Superfast Proton Transfer ^† Tolbert, Laren M.; Solntsev, Kyril M. Accounts of Chemical Research, Vol. 35, Issue 1 https://doi.org/10.1021/ar990109f	journal	January 2002
Acidity Functions for Strongly Basic Solutions Bowden, Keith Chemical Reviews, Vol. 66, Issue 2 https://doi.org/10.1021/cr60240a001	journal	April 1966
Proton transfer in mixed water-organic solvent solutions: correlation between rate, equilibrium constant, and the proton free energy of transfer Pines, Ehud; Fleming, Graham R. The Journal of Physical Chemistry, Vol. 95, Issue 25 https://doi.org/10.1021/j100178a036	journal	December 1991
Excited-state proton transfer of protonated 1-aminopyrene complexes with .beta.-cyclodextrin Hansen, John E.; Pines, Ehud; Fleming, Graham R. The Journal of Physical Chemistry, Vol. 96, Issue 17 https://doi.org/10.1021/j100196a011	journal	August 1992
Excited-state proton-transfer kinetics: a theoretical model Arnaut, Luis G.; Formosinho, Sebastiao J. The Journal of Physical Chemistry, Vol. 92, Issue 3 https://doi.org/10.1021/j100314a022	journal	February 1988
Solvent reorganization in optical and thermal electron-transfer processes Brunschwig, Bruce S.; Ehrenson, Stanton; Sutin, Norman The Journal of Physical Chemistry, Vol. 90, Issue 16 https://doi.org/10.1021/j100407a037	journal	July 1986
Picosecond kinetics of the excited-state, proton-transfer reaction of 1-naphthol in water Webb, S. P.; Philips, Laura A.; Yeh, Sheila W. The Journal of Physical Chemistry, Vol. 90, Issue 21 https://doi.org/10.1021/j100412a053	journal	October 1986
Analysis of two-state excited-state reactions. The fluorescence decay of 2-naphthol Laws, William R.; Brand, Ludwig. The Journal of Physical Chemistry, Vol. 83, Issue 7 https://doi.org/10.1021/j100470a007	journal	April 1979
Theoretical relations among rate constants, barriers, and Broensted slopes of chemical reactions Marcus, Rudolph A. The Journal of Physical Chemistry, Vol. 72, Issue 3 https://doi.org/10.1021/j100849a019	journal	March 1968
Slope of free energy plots in chemical kinetics Cohen, Audrey O.; Marcus, Rudolph A. The Journal of Physical Chemistry, Vol. 72, Issue 12 https://doi.org/10.1021/j100858a052	journal	November 1968
Proton Transfer Quenching of the MLCT Excited State of Ru(phen)2dppz2+ in Homogeneous Solution and Bound to DNA Turro, Claudia; Bossmann, Stefan H.; Jenkins, Yonchu Journal of the American Chemical Society, Vol. 117, Issue 35 https://doi.org/10.1021/ja00140a020	journal	September 1995
Application of Marcus theory to photochemical proton-transfer reactions. I. An exploratory study of empirical modifications of the basic equations Yates, Keith. Journal of the American Chemical Society, Vol. 108, Issue 21 https://doi.org/10.1021/ja00281a011	journal	October 1986
Intramolecular long-distance electron transfer in radical anions. The effects of free energy and solvent on the reaction rates Miller, J. R.; Calcaterra, L. T.; Closs, G. L. Journal of the American Chemical Society, Vol. 106, Issue 10 https://doi.org/10.1021/ja00322a058	journal	May 1984
Diffusion Measurements, at 25°, of Aqueous Solutions of Amino Acids, Peptides and Sugars Longsworth, L. G. Journal of the American Chemical Society, Vol. 75, Issue 22 https://doi.org/10.1021/ja01118a065	journal	November 1953
Mechanism of H ₂ Evolution from a Photogenerated Hydridocobaloxime Dempsey, Jillian L.; Winkler, Jay R.; Gray, Harry B. Journal of the American Chemical Society, Vol. 132, Issue 47 https://doi.org/10.1021/ja109351h	journal	December 2010
Reexamination of the Rehm–Weller Data Set Reveals Electron Transfer Quenching That Follows a Sandros–Boltzmann Dependence on Free Energy Farid, Samir; Dinnocenzo, Joseph P.; Merkel, Paul B. Journal of the American Chemical Society, Vol. 133, Issue 30 https://doi.org/10.1021/ja2024367	journal	August 2011
The Central Role of Bicarbonate in the Electrochemical Reduction of Carbon Dioxide on Gold Dunwell, Marco; Lu, Qi; Heyes, Jeffrey M. Journal of the American Chemical Society, Vol. 139, Issue 10 https://doi.org/10.1021/jacs.6b13287	journal	March 2017
Observation of Photovoltaic Action from Photoacid-Modified Nafion Due to Light-Driven Ion Transport White, William; Sanborn, Christopher D.; Reiter, Ronald S. Journal of the American Chemical Society, Vol. 139, Issue 34 https://doi.org/10.1021/jacs.7b00974	journal	May 2017
Bicarbonate Is Not a General Acid in Au-Catalyzed CO ₂ Electroreduction Wuttig, Anna; Yoon, Youngmin; Ryu, Jaeyune Journal of the American Chemical Society, Vol. 139, Issue 47 https://doi.org/10.1021/jacs.7b08345	journal	November 2017
Ultrafast Proton Transport between a Hydroxy Acid and a Nitrogen Base along Solvent Bridges Governed by the Hydroxide/Methoxide Transfer Mechanism Ekimova, Maria; Hoffmann, Felix; Bekçioğlu-Neff, Gül Journal of the American Chemical Society, Vol. 141, Issue 37 https://doi.org/10.1021/jacs.9b03471	journal	August 2019
Photohydration of aromatic alkenes. Catalytic phenomena and structure-reactivity studies Wan, Peter; Yates, Keith The Journal of Organic Chemistry, Vol. 48, Issue 6 https://doi.org/10.1021/jo00154a024	journal	March 1983
Nonlinear Free Energy Relations for Adiabatic Proton Transfer Reactions in a Polar Environment. I. Fixed Proton Donor−Acceptor Separation Kiefer, Philip M.; Hynes, James T. The Journal of Physical Chemistry A, Vol. 106, Issue 9 https://doi.org/10.1021/jp0134244	journal	March 2002
Nonlinear Free Energy Relations for Adiabatic Proton Transfer Reactions in a Polar Environment. II. Inclusion of the Hydrogen Bond Vibration Kiefer, Philip M.; Hynes, James T. The Journal of Physical Chemistry A, Vol. 106, Issue 9 https://doi.org/10.1021/jp013425w	journal	February 2002
Protolytic Photodissociation and Proton-Induced Quenching of 1-Naphthol and 2-Octadecyl-1-Naphthol in Micelles Solntsev, Kyril M.; Al-Ainain, Sami Abou; Il'ichev, Yuri V. The Journal of Physical Chemistry A, Vol. 108, Issue 40 https://doi.org/10.1021/jp040201f	journal	September 2004
Elementary Steps in Excited-State Proton Transfer ^† Agmon, Noam The Journal of Physical Chemistry A, Vol. 109, Issue 1 https://doi.org/10.1021/jp047465m	journal	January 2005
Ultrafast Proton Transfer of Three Novel Quinone Cyanine Photoacids Presiado, Itay; Karton-Lifshin, Naama; Erez, Yuval The Journal of Physical Chemistry A, Vol. 116, Issue 27 https://doi.org/10.1021/jp304123y	journal	July 2012
Ultrafast Excited-State Proton-Transfer Reaction of 1-Naphthol-3,6-Disulfonate and Several 5-Substituted 1-Naphthol Derivatives Prémont-Schwarz, Mirabelle; Barak, Tamar; Pines, Dina The Journal of Physical Chemistry B, Vol. 117, Issue 16 https://doi.org/10.1021/jp308746x	journal	February 2013
How Fast Can a Proton-Transfer Reaction Be beyond the Solvent-Control Limit? Simkovitch, Ron; Shomer, Shay; Gepshtein, Rinat The Journal of Physical Chemistry B, Vol. 119, Issue 6 https://doi.org/10.1021/jp506011e	journal	August 2014
Photochemistry of “Super”-Photoacids. Solvent Effects Solntsev, Kyril M.; Huppert, Dan; Agmon, Noam The Journal of Physical Chemistry A, Vol. 103, Issue 35 https://doi.org/10.1021/jp9902295	journal	September 1999
Photocurrent generation based on a light-driven proton pump in an artificial liquid membrane Xie, Xiaojiang; Crespo, Gastón A.; Mistlberger, Günter Nature Chemistry, Vol. 6, Issue 3 https://doi.org/10.1038/nchem.1858	journal	February 2014
Clarification of mechanisms of protonic photovoltaic action initiated by photoexcitation of strong photoacids covalently bound to hydrated Nafion cation-exchange membranes wetted by aqueous electrolytes Luo, Simon; White, William; Cardon, Joseph M. Energy & Environmental Science, Vol. 14, Issue 9 https://doi.org/10.1039/D1EE00482D	journal	January 2021
Alcohol tracer diffusion, density, NMR and FTIR studies of aqueous ethanol and 2,2,2-trifluoroethanol solutions at 25°C Harris, Kenneth R.; Newitt, Paula J.; Derlacki, Z. J. Journal of the Chemical Society, Faraday Transactions, Vol. 94, Issue 14 https://doi.org/10.1039/a802567c	journal	January 1998
Exploring the use of APTS as a fluorescent reporter dye for continuous glucose sensing Sharrett, Zachary; Gamsey, Soya; Hirayama, Lacie Organic & Biomolecular Chemistry, Vol. 7, Issue 7 https://doi.org/10.1039/b821934f	journal	January 2009
Kinetics of proton transfer processes Eigen, M. Discussions of the Faraday Society, Vol. 39 https://doi.org/10.1039/df9653900007	journal	January 1965
On the Theory of Oxidation‐Reduction Reactions Involving Electron Transfer. I Marcus, R. A. The Journal of Chemical Physics, Vol. 24, Issue 5 https://doi.org/10.1063/1.1742723	journal	May 1956
Accelerating slow excited state proton transfer Stewart, D. J.; Concepcion, J. J.; Brennaman, M. K. Proceedings of the National Academy of Sciences, Vol. 110, Issue 3 https://doi.org/10.1073/pnas.1220742110	journal	December 2012
Self-dissociation and protonic charge transport in water and Eigen, Manfred; De Maeyer, L. Proceedings of the Royal Society of London. Series A. Mathematical and Physical Sciences, Vol. 247, Issue 1251, p. 505-533 https://doi.org/10.1098/rspa.1958.0208	journal	October 1958
Real-Time Observation of Carbonic Acid Formation in Aqueous Solution Adamczyk, K.; Premont-Schwarz, M.; Pines, D. Science, Vol. 326, Issue 5960 https://doi.org/10.1126/science.1180060	journal	November 2009
Intramolecular Long-Distance Electron Transfer in Organic Molecules Closs, G. L.; Miller, J. R. Science, Vol. 240, Issue 4851 https://doi.org/10.1126/science.240.4851.440	journal	April 1988
The Application of the Marcus Relation to Reactions in Solution Albery, W. J. Annual Review of Physical Chemistry, Vol. 31, Issue 1 https://doi.org/10.1146/annurev.pc.31.100180.001303	journal	October 1980
Imaging Water-Splitting Electrocatalysts with pH-Sensing Confocal Fluorescence Microscopy Leenheer, Andrew J.; Atwater, Harry A. Journal of The Electrochemical Society, Vol. 159, Issue 9 https://doi.org/10.1149/2.022209jes	journal	January 2012
Understanding Transport at the Acid-Alkaline Interface of Bipolar Membranes Grew, Kyle N.; McClure, Joshua P.; Chu, Deryn Journal of The Electrochemical Society, Vol. 163, Issue 14 https://doi.org/10.1149/2.0941614jes	journal	January 2016
Identification of Photoacidic Behavior Using AC and Open-Circuit Photoelectrochemical Techniques Glancy, Jennifer; Luo, Simon; Kim, Tea-Yon ECS Journal of Solid State Science and Technology, Vol. 11, Issue 10 https://doi.org/10.1149/2162-8777/ac71ff	journal	October 2022
Fast elementary steps in chemical reaction mechanisms Eigen, M. Pure and Applied Chemistry, Vol. 6, Issue 1 https://doi.org/10.1351/pac196306010097	journal	January 1963
Die katalytische Zersetzung des Nitramids und ihre physikalisch-chemische Bedeutung Brönsted, J. N.; Pedersen, Kai Zeitschrift für Physikalische Chemie, Vol. 108U, Issue 1 https://doi.org/10.1515/zpch-1924-10814	journal	January 1924
Ultrafast Protonation of Cyanate Anion in Aqueous Solution Adamczyk, Katrin; Dreyer, Jens; Pines, Dina Israel Journal of Chemistry, Vol. 49, Issue 2 https://doi.org/10.1560/IJC.49.2.217	journal	July 2009
Cation-Enhanced Deprotonation of Water by a Strong Photobase Munitz, Noga; Avital, Yotam; Pines, Dina Israel Journal of Chemistry, Vol. 49, Issue 2 https://doi.org/10.1560/IJC.49.2.261	journal	July 2009

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