Photoinduced Bimolecular Electron Transfer in Ionic Liquids: Cationic Electron Donors

Wu, Boning; Liang, Min; Zmich, Nicole; Hatcher, Jasmine; Lall-Ramnarine, Sharon I.; Wishart, James F.; Maroncelli, Mark; Castner, Edward W.

doi:10.1021/acs.jpcb.7b12542

Title: Photoinduced Bimolecular Electron Transfer in Ionic Liquids: Cationic Electron Donors

Journal Article · Mon Jan 29 00:00:00 EST 2018 · Journal of Physical Chemistry. B, Condensed Matter, Materials, Surfaces, Interfaces and Biophysical Chemistry

DOI:https://doi.org/10.1021/acs.jpcb.7b12542· OSTI ID:1425075

^[1]; Liang, Min ^[1]; Zmich, Nicole ^[2]; Hatcher, Jasmine ^[3]; Lall-Ramnarine, Sharon I. ^[4];

^[2];

^[5];

^[1]

Rutgers Univ., Piscataway, NJ (United States). Dept. of Chemistry and Chemical Biology
Brookhaven National Lab. (BNL), Upton, NY (United States). Chemistry Division
The Graduate Center of CUNY, New York, NY (United States); Hunter College, New York, NY (United States)
Queensborough Community College, Bayside, NY (United States). Dept. of Chemistry
Pennsylvania State Univ., University Park, PA (United States). Dept. of Chemistry

Recently, we have reported a systematic study of photoinduced electron-transfer reactions in ionic liquid solvents using neutral and anionic electron donors and a series of cyano-substituted anthracene acceptors [Wu, B.; Maroncelli, M.; Castner, E. W., Jr.Photoinduced Bimolecular Electron Transfer in Ionic Liquids. J. Am. Chem. Soc.139, 2017, 14568]. In this paper, we report complementary results for a cationic class of 1-alkyl-4-dimethylaminopyridinium electron donors. Reductive quenching of cyano-substituted anthracene fluorophores by these cationic quenchers is studied in solutions of acetonitrile and the ionic liquid 1-ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide. Varying the length of the alkyl chain permits tuning of the quencher diffusivities in solution. The observed quenching kinetics are interpreted using a diffusion-reaction analysis. Finally, together with results from the prior study, these results show that the intrinsic electron-transfer rate constant does not depend on the quencher charge in this family of reactions.

View Accepted Manuscript (DOE)

Cite

Export

Save

Research Organization:: Brookhaven National Laboratory (BNL), Upton, NY (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: SC0012704; SC0001780; SC0008640

OSTI ID:: 1425075

Report Number(s):: BNL-203219-2018-JAAM; TRN: US1802032

Journal Information:: Journal of Physical Chemistry. B, Condensed Matter, Materials, Surfaces, Interfaces and Biophysical Chemistry, Vol. 122, Issue 8; ISSN 1520-6106

Publisher:: American Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: English

Citation Metrics:

Cited by: 13 works

Citation information provided by
Web of Science

References (62)

Photoinduced Bimolecular Electron Transfer in Ionic Liquids Wu, Boning; Maroncelli, Mark; Castner, Edward W. Journal of the American Chemical Society, Vol. 139, Issue 41 https://doi.org/10.1021/jacs.7b07611	journal	October 2017
Bimolecular Photoinduced Electron Transfer in Imidazolium-Based Room-Temperature Ionic Liquids Is Not Faster than in Conventional Solvents Koch, Marius; Rosspeintner, Arnulf; Angulo, Gonzalo Journal of the American Chemical Society, Vol. 134, Issue 8 https://doi.org/10.1021/ja208265x	journal	February 2012
Bimolecular Electron Transfer in Ionic Liquids: Are Reaction Rates Anomalously High? Liang, Min; Kaintz, Anne; Baker, Gary A. The Journal of Physical Chemistry B, Vol. 116, Issue 4 https://doi.org/10.1021/jp210892c	journal	January 2012
Solute Diffusion in Ionic Liquids, NMR Measurements and Comparisons to Conventional Solvents Kaintz, Anne; Baker, Gary; Benesi, Alan The Journal of Physical Chemistry B, Vol. 117, Issue 39 https://doi.org/10.1021/jp405393d	journal	September 2013
Photoinduced Bimolecular Electron Transfer from Cyano Anions in Ionic Liquids Wu, Boning; Liang, Min; Maroncelli, Mark The Journal of Physical Chemistry B, Vol. 119, Issue 46 https://doi.org/10.1021/acs.jpcb.5b09216	journal	November 2015
Electron transfers in chemistry and biology Marcus, R. A.; Sutin, Norman Biochimica et Biophysica Acta (BBA) - Reviews on Bioenergetics, Vol. 811, Issue 3 https://doi.org/10.1016/0304-4173(85)90014-X	journal	August 1985
Energy applications of ionic liquids Wishart, James F. Energy & Environmental Science, Vol. 2, Issue 9 https://doi.org/10.1039/b906273d	journal	January 2009
Energy applications of ionic liquids MacFarlane, Douglas R.; Tachikawa, Naoki; Forsyth, Maria Energy Environ. Sci., Vol. 7, Issue 1 https://doi.org/10.1039/C3EE42099J	journal	January 2014
Ionic liquids as tailored media for the synthesis and processing of energy conversion materials Eshetu, Gebrekidan Gebresilassie; Armand, Michel; Ohno, Hiroyuki Energy & Environmental Science, Vol. 9, Issue 1 https://doi.org/10.1039/C5EE02284C	journal	January 2016
Solvent-Controlled Intramolecular Electron Transfer in Ionic Liquids Li, Xiang; Liang, Min; Chakraborty, Anjan The Journal of Physical Chemistry B, Vol. 115, Issue 20 https://doi.org/10.1021/jp200339e	journal	May 2011
A Comparison of Electron-Transfer Dynamics in Ionic Liquids and Neutral Solvents Lee, Heather Y.; Issa, Joseph B.; Isied, Stephan S. The Journal of Physical Chemistry C, Vol. 116, Issue 8 https://doi.org/10.1021/jp208852r	journal	February 2012
Ultrafast solvation dynamics and charge transfer reactions in room temperature ionic liquids Nagasawa, Yutaka; Miyasaka, Hiroshi Phys. Chem. Chem. Phys., Vol. 16, Issue 26 https://doi.org/10.1039/C3CP55465A	journal	January 2014
Electron-Transfer Dynamics for a Donor–Bridge–Acceptor Complex in Ionic Liquids DeVine, Jessalyn A.; Labib, Marena; Harries, Megan E. The Journal of Physical Chemistry B, Vol. 119, Issue 34 https://doi.org/10.1021/acs.jpcb.5b03320	journal	July 2015
Photoexcitation dynamics of p-nitroaniline and N,N-dimethyl-p-nitroaniline in 1-alkyl-3-methylimidazolium-cation based ionic liquids with different alkyl-chain lengths Kimura, Y.; Ibaraki, S.; Hirano, R. Physical Chemistry Chemical Physics, Vol. 19, Issue 33 https://doi.org/10.1039/C7CP03610H	journal	January 2017
Photoinduced Electron Transfer Reaction in Room Temperature Ionic Liquids: A Combined Laser Flash Photolysis and Fluorescence Study Paul, Aniruddha; Samanta, Anunay The Journal of Physical Chemistry B, Vol. 111, Issue 8 https://doi.org/10.1021/jp067481e	journal	March 2007
Photoinduced Electron-Transfer Reactions in Two Room-Temperature Ionic Liquids: 1-Butyl-3-methylimidazolium Hexafluorophosphate and 1-Octyl-3-methylimidazolium Hexafluorophosphate ^† Vieira, Rebecca C.; Falvey, Daniel E. The Journal of Physical Chemistry B, Vol. 111, Issue 18 https://doi.org/10.1021/jp0630471	journal	May 2007
How good is the generalized Langevin equation to describe the dynamics of photo-induced electron transfer in fluid solution? Angulo, Gonzalo; Jedrak, Jakub; Ochab-Marcinek, Anna The Journal of Chemical Physics, Vol. 146, Issue 24 https://doi.org/10.1063/1.4990044	journal	June 2017
Intramolecular Charge-Transfer Dynamics in Covalently Linked Perylene−Dimethylaniline and Cyanoperylene−Dimethylaniline Banerji, Natalie; Angulo, Gonzalo; Barabanov, Igor The Journal of Physical Chemistry A, Vol. 112, Issue 40 https://doi.org/10.1021/jp803621z	journal	October 2008
Complete Solvation Response of Coumarin 153 in Ionic Liquids Zhang, Xin-Xing; Liang, Min; Ernsting, Nikolaus P. The Journal of Physical Chemistry B, Vol. 117, Issue 16 https://doi.org/10.1021/jp305430a	journal	August 2012
Solvation and Rotational Dynamics of Coumarin 153 in Ionic Liquids: Comparisons to Conventional Solvents Jin, Hui; Baker, Gary A.; Arzhantsev, Sergei The Journal of Physical Chemistry B, Vol. 111, Issue 25 https://doi.org/10.1021/jp070923h	journal	June 2007
Ionic Liquids: Structure and Photochemical Reactions Castner, Edward W.; Margulis, Claudio J.; Maroncelli, Mark Annual Review of Physical Chemistry, Vol. 62, Issue 1 https://doi.org/10.1146/annurev-physchem-032210-103421	journal	May 2011
Intermolecular Dynamics, Interactions, and Solvation in Ionic Liquids Castner, Edward W.; Wishart, James F.; Shirota, Hideaki Accounts of Chemical Research, Vol. 40, Issue 11 https://doi.org/10.1021/ar700169g	journal	November 2007
Solute Rotation in Ionic Liquids: Size, Shape, and Electrostatic Effects Rumble, Christopher A.; Uitvlugt, Caleb; Conway, Brian The Journal of Physical Chemistry B, Vol. 121, Issue 19 https://doi.org/10.1021/acs.jpcb.7b01704	journal	May 2017
Dynamics in a Room-Temperature Ionic Liquid from the Cation Perspective: 2D IR Vibrational Echo Spectroscopy Yamada, Steven A.; Bailey, Heather E.; Tamimi, Amr Journal of the American Chemical Society, Vol. 139, Issue 6 https://doi.org/10.1021/jacs.6b12011	journal	February 2017
Dynamics of a Room Temperature Ionic Liquid in Supported Ionic Liquid Membranes vs the Bulk Liquid: 2D IR and Polarized IR Pump–Probe Experiments Shin, Jae Yoon; Yamada, Steven A.; Fayer, Michael D. Journal of the American Chemical Society, Vol. 139, Issue 1 https://doi.org/10.1021/jacs.6b10695	journal	December 2016
How Is Diffusion of Neutral and Charged Tracers Related to the Structure and Dynamics of a Room-Temperature Ionic Liquid? Large Deviations from Stokes–Einstein Behavior Explained Araque, Juan C.; Yadav, Sharad K.; Shadeck, Michael The Journal of Physical Chemistry B, Vol. 119, Issue 23 https://doi.org/10.1021/acs.jpcb.5b01093	journal	April 2015
Communication: Unusual structure and transport in ionic liquid-hexane mixtures Liang, Min; Khatun, Sufia; Castner, Edward W. The Journal of Chemical Physics, Vol. 142, Issue 12 https://doi.org/10.1063/1.4916388	journal	March 2015
The Influence of Water on the Alkyl Region Structure in Variable Chain Length Imidazolium-Based Ionic Liquid/Water Mixtures Thomaz, Joseph E.; Lawler, Christian M.; Fayer, Michael D. The Journal of Physical Chemistry B, Vol. 120, Issue 39 https://doi.org/10.1021/acs.jpcb.6b07853	journal	September 2016
Dynamics of water, methanol, and ethanol in a room temperature ionic liquid Kramer, Patrick L.; Giammanco, Chiara H.; Fayer, Michael D. The Journal of Chemical Physics, Vol. 142, Issue 21 https://doi.org/10.1063/1.4914156	journal	June 2015
Impact of Hydrogen Bonding on the Dynamics and Structure of Protic Ionic Liquid/Water Binary Mixtures Bailey, Heather E.; Wang, Yong-Lei; Fayer, Michael D. The Journal of Physical Chemistry B, Vol. 121, Issue 36 https://doi.org/10.1021/acs.jpcb.7b06376	journal	August 2017
Ultrafast Elementary Photochemical Processes of Organic Molecules in Liquid Solution Kumpulainen, Tatu; Lang, Bernhard; Rosspeintner, Arnulf Chemical Reviews, Vol. 117, Issue 16 https://doi.org/10.1021/acs.chemrev.6b00491	journal	December 2016
1-Alkyl-(N,N-dimethylamino)pyridinium bromides: inhibitory effect on virulence factors of Candida albicans and on the growth of bacterial pathogens Sundararaman, Muthuraman; Rajesh Kumar, Radhakrishnan; Venkatesan, Perumal Journal of Medical Microbiology, Vol. 62, Issue 2 https://doi.org/10.1099/jmm.0.050070-0	journal	February 2013
1-Alkyl-4-dialkylaminopyridinium Halides as Phase-Transfer Catalysts in Dichlorocarbene Reactions Kupetis, Gytis-Kazimieras; šaduikis, Gintautas; Nivinskienø, Ona Monatshefte f?r Chemie / Chemical Monthly, Vol. 133, Issue 3 https://doi.org/10.1007/s007060200009	journal	March 2002
A Computational and Experimental Study of the Heat Transfer Properties of Nine Different Ionic Liquids Tenney, Craig M.; Massel, Marjorie; Mayes, Jason M. Journal of Chemical & Engineering Data, Vol. 59, Issue 2 https://doi.org/10.1021/je400858t	journal	January 2014
A comparative study of electrochemical degradation of imidazolium and pyridinium ionic liquids: A reaction pathway and ecotoxicity evaluation Pieczyńska, Aleksandra; Ofiarska, Aleksandra; Borzyszkowska, Agnieszka Fiszka Separation and Purification Technology, Vol. 156 https://doi.org/10.1016/j.seppur.2015.10.045	journal	December 2015
Aging Effects on the Properties of Imidazolium-, Quaternary Ammonium-, Pyridinium-, and Pyrrolidinium-Based Ionic Liquids Used in Fuel and Energy Production Fox, Elise B.; Smith, L. Taylor; Williamson, Tyler K. Energy & Fuels, Vol. 27, Issue 11 https://doi.org/10.1021/ef401148j	journal	August 2013
Solvent as Electron Donor: Donor/Acceptor Electronic Coupling Is a Dynamical Variable Castner, Edward W.; Kennedy, Darcy; Cave, Robert J. The Journal of Physical Chemistry A, Vol. 104, Issue 13 https://doi.org/10.1021/jp9936852	journal	March 2000
Direct Measurements of the Charge-Recombination Dynamics of Geminate Ion Pairs Formed upon Electron-Transfer Quenching at High Donor Concentration Vauthey, Eric The Journal of Physical Chemistry A, Vol. 105, Issue 2 https://doi.org/10.1021/jp0023260	journal	January 2001
Radiation boundary conditions in collisional quenching of fluorescence; determination by frequency-domain fluorometry Joshi, Nanda; Johnson, Michael L.; Gryczynski, Ignacy Chemical Physics Letters, Vol. 135, Issue 3 https://doi.org/10.1016/0009-2614(87)85142-4	journal	April 1987
A subpicosecond, subnanosecond and steady‐state study of diffusion‐influenced fluorescence quenching Eads, Daniel D.; Dismer, Berit G.; Fleming, Graham R. The Journal of Chemical Physics, Vol. 93, Issue 2 https://doi.org/10.1063/1.459177	journal	July 1990
Influence of diffusion on photoinduced electron transfer Song, L.; Dorfman, R. C.; Swallen, S. F. The Journal of Physical Chemistry, Vol. 95, Issue 9 https://doi.org/10.1021/j100162a003	journal	May 1991
Distance-dependent fluorescence quenching observed by frequency-domain fluorometry Lakowicz, Joseph R.; Kuśba, Józef; Szmacinski, Henryk Chemical Physics Letters, Vol. 206, Issue 5-6 https://doi.org/10.1016/0009-2614(93)80167-N	journal	May 1993
Experimental and Theoretical Analysis of Photoinduced Electron Transfer: Including the Role of Liquid Structure Swallen, S. F.; Weidemaier, Kristin; Tavernier, H. L. The Journal of Physical Chemistry, Vol. 100, Issue 20 https://doi.org/10.1021/jp953583l	journal	January 1996
Solute–solute spatial distribution in hydrogen bonding liquids probed with time-dependent intermolecular electron transfer Tavernier, H. L.; Fayer, M. D. The Journal of Chemical Physics, Vol. 114, Issue 10 https://doi.org/10.1063/1.1349705	journal	January 2001
Photoinduced electron transfer and geminate recombination for photoexcited acceptors in a pure donor solvent Saik, V. O.; Goun, A. A.; Fayer, M. D. The Journal of Chemical Physics, Vol. 120, Issue 20 https://doi.org/10.1063/1.1712826	journal	May 2004
Kinetics and Yields of Electron Transfer in the Inverted Region Gladkikh, V.; Burshtein, A. I.; Angulo, G. The Journal of Physical Chemistry A, Vol. 108, Issue 32 https://doi.org/10.1021/jp0492669	journal	August 2004
On the Coherent Description of Diffusion-Influenced Fluorescence Quenching Experiments Rosspeintner, Arnulf; Kattnig, Daniel R.; Angulo, Gonzalo Chemistry - A European Journal, Vol. 13, Issue 22 https://doi.org/10.1002/chem.200700106	journal	July 2007
On the Coherent Description of Diffusion-Influenced Fluorescence Quenching Experiments II: Early Events Angulo, Gonzalo; Kattnig, Daniel R.; Rosspeintner, Arnulf Chemistry - A European Journal, Vol. 16, Issue 7 https://doi.org/10.1002/chem.200901693	journal	February 2010
Spurious Observation of the Marcus Inverted Region in Bimolecular Photoinduced Electron Transfer Rosspeintner, Arnulf; Koch, Marius; Angulo, Gonzalo Journal of the American Chemical Society, Vol. 134, Issue 28 https://doi.org/10.1021/ja3049095	journal	July 2012
Bimolecular Photoinduced Electron Transfer Beyond the Diffusion Limit: The Rehm–Weller Experiment Revisited with Femtosecond Time Resolution Rosspeintner, Arnulf; Angulo, Gonzalo; Vauthey, Eric Journal of the American Chemical Society, Vol. 136, Issue 5 https://doi.org/10.1021/ja4118279	journal	January 2014
Lifetimes of Radical Anions of Dicyanoanthracene, Phenazine, and Anthraquinone in the Excited State from the Selective Electron-Transfer Quenching Fujita, Morifumi; Ishida, Akito; Majima, Tetsuro The Journal of Physical Chemistry, Vol. 100, Issue 13 https://doi.org/10.1021/jp953203w	journal	January 1996
Exploring the Effect of Structural Modification on the Physical Properties of Various Ionic Liquids Lall-Ramnarine, Sharon I.; Hatcher, Jasmine; Castano, Alejandra ECS Transactions, Vol. 33, Issue 7 https://doi.org/10.1149/1.3484823	journal	October 2010
Binary Ionic Liquid Mixtures for Supercapacitor Applications Lall-Ramnarine, S.; Suarez, S.; Zmich, N. ECS Transactions, Vol. 64, Issue 4 https://doi.org/10.1149/06404.0057ecst	journal	August 2014
Fluorescence Probing of Temperature-Dependent Dynamics and Friction in Ionic Liquid Local Environments ^† Funston, Alison M.; Fadeeva, Tatiana A.; Wishart, James F. The Journal of Physical Chemistry B, Vol. 111, Issue 18 https://doi.org/10.1021/jp068298o	journal	May 2007
An Improved Diffusion-Ordered Spectroscopy Experiment Incorporating Bipolar-Gradient Pulses Wu, D. H.; Chen, A. D.; Johnson, C. S. Journal of Magnetic Resonance, Series A, Vol. 115, Issue 2 https://doi.org/10.1006/jmra.1995.1176	journal	August 1995
Theory of diffusion-influenced fluorescence quenching Szabo, Attila The Journal of Physical Chemistry, Vol. 93, Issue 19 https://doi.org/10.1021/j100356a011	journal	September 1989
Time-Dependent Rate Coefficients for Diffusion-Influenced Reactions with Centrosymmetric Potentials Dudko, Olga K.; Szabo, Attila The Journal of Physical Chemistry B, Vol. 109, Issue 12 https://doi.org/10.1021/jp044433q	journal	March 2005
Outer-sphere electron transfer in polar solvents Zusman, L. D. Chemical Physics, Vol. 49, Issue 2 https://doi.org/10.1016/0301-0104(80)85267-0	journal	July 1980
Dynamical solvent effect in electron transfer reactions occurring in a mixture of two polar solvents Zusman, Leonid The Journal of Chemical Physics, Vol. 102, Issue 6 https://doi.org/10.1063/1.468688	journal	February 1995
Dynamic solvent effects on outer‐sphere electron transfer Rips, Ilya; Jortner, Joshua The Journal of Chemical Physics, Vol. 87, Issue 4 https://doi.org/10.1063/1.453184	journal	August 1987
Intramolecular vibrational excitations accompanying solvent‐controlled electron transfer reactions Jortner, Joshua; Bixon, Mordechai The Journal of Chemical Physics, Vol. 88, Issue 1 https://doi.org/10.1063/1.454632	journal	January 1988
Efficiencies of photoinduced electron-transfer reactions: role of the Marcus inverted region in return electron transfer within geminate radical-ion pairs Gould, Ian R.; Ege, Deniz; Moser, Jacques E. Journal of the American Chemical Society, Vol. 112, Issue 11 https://doi.org/10.1021/ja00167a027	journal	May 1990

Cited By (1)

Microscopic Structural and Dynamic Features in Triphilic Room Temperature Ionic Liquids Lo Celso, Fabrizio; Appetecchi, Giovanni B.; Simonetti, Elisabetta Frontiers in Chemistry, Vol. 7 https://doi.org/10.3389/fchem.2019.00285	journal	May 2019