Photoinduced Bimolecular Electron Transfer from Cyano Anions in Ionic Liquids
Abstract
Ionic liquids with electron-donating anions are used to investigate rates and mechanisms of photoinduced bimolecular electron transfer to the photoexcited acceptor 9,10-dicyanoanthracene (9,10-DCNA). The set of five cyano anion ILs studied comprises the 1-ethyl-3-methylimidazolium cation paired with each of these five anions: selenocyanate, thiocyanate, dicyanamide, tricyanomethanide, and tetracyano-borate. Measurements with these anions dilute in acetonitrile and 1-ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)-amide show that the selenocyanate and tricyanomethanide anions are strong quenchers of the 9,10-DCNA fluorescence, thiocyanate is a moderately strong quencher, dicyanamide is a weak quencher, and no quenching is observed for tetracyanoborate. Quenching rates are obtained from both time-resolved fluorescence transients and time-integrated spectra. Finally, application of a Smoluchowski diffusion-and-reaction model showed that the complex kinetics observed can be fit using only two adjustable parameters, D and V0, where D is the relative diffusion coefficient between donor and acceptor and V0 is the value of the electronic coupling at donor-acceptor contact.
- Authors:
-
- Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, 610 Taylor Road, Piscataway, New Jersey 08854, United States
- Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802, United States
- Publication Date:
- Research Org.:
- Rutgers Univ., Piscataway, NJ (United States); Pennsylvania State Univ., University Park, PA (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC), Basic Energy Sciences (BES)
- OSTI Identifier:
- 1248414
- Alternate Identifier(s):
- OSTI ID: 1434921
- Grant/Contract Number:
- SC0001780; SC0008640
- Resource Type:
- Published Article
- Journal Name:
- Journal of Physical Chemistry. B
- Additional Journal Information:
- Journal Name: Journal of Physical Chemistry. B Journal Volume: 119 Journal Issue: 46; Journal ID: ISSN 1520-6106
- Publisher:
- American Chemical Society
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Citation Formats
Wu, Boning, Liang, Min, Maroncelli, Mark, and Castner, Jr., Edward W. Photoinduced Bimolecular Electron Transfer from Cyano Anions in Ionic Liquids. United States: N. p., 2015.
Web. doi:10.1021/acs.jpcb.5b09216.
Wu, Boning, Liang, Min, Maroncelli, Mark, & Castner, Jr., Edward W. Photoinduced Bimolecular Electron Transfer from Cyano Anions in Ionic Liquids. United States. https://doi.org/10.1021/acs.jpcb.5b09216
Wu, Boning, Liang, Min, Maroncelli, Mark, and Castner, Jr., Edward W. Mon .
"Photoinduced Bimolecular Electron Transfer from Cyano Anions in Ionic Liquids". United States. https://doi.org/10.1021/acs.jpcb.5b09216.
@article{osti_1248414,
title = {Photoinduced Bimolecular Electron Transfer from Cyano Anions in Ionic Liquids},
author = {Wu, Boning and Liang, Min and Maroncelli, Mark and Castner, Jr., Edward W.},
abstractNote = {Ionic liquids with electron-donating anions are used to investigate rates and mechanisms of photoinduced bimolecular electron transfer to the photoexcited acceptor 9,10-dicyanoanthracene (9,10-DCNA). The set of five cyano anion ILs studied comprises the 1-ethyl-3-methylimidazolium cation paired with each of these five anions: selenocyanate, thiocyanate, dicyanamide, tricyanomethanide, and tetracyano-borate. Measurements with these anions dilute in acetonitrile and 1-ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)-amide show that the selenocyanate and tricyanomethanide anions are strong quenchers of the 9,10-DCNA fluorescence, thiocyanate is a moderately strong quencher, dicyanamide is a weak quencher, and no quenching is observed for tetracyanoborate. Quenching rates are obtained from both time-resolved fluorescence transients and time-integrated spectra. Finally, application of a Smoluchowski diffusion-and-reaction model showed that the complex kinetics observed can be fit using only two adjustable parameters, D and V0, where D is the relative diffusion coefficient between donor and acceptor and V0 is the value of the electronic coupling at donor-acceptor contact.},
doi = {10.1021/acs.jpcb.5b09216},
journal = {Journal of Physical Chemistry. B},
number = 46,
volume = 119,
place = {United States},
year = {Mon Nov 09 00:00:00 EST 2015},
month = {Mon Nov 09 00:00:00 EST 2015}
}
https://doi.org/10.1021/acs.jpcb.5b09216
Web of Science
Works referenced in this record:
Heterogeneity in a room-temperature ionic liquid: Persistent local environments and the red-edge effect
journal, January 2006
- Hu, Z.; Margulis, C. J.
- Proceedings of the National Academy of Sciences, Vol. 103, Issue 4
Bimolecular Electron Transfer in Ionic Liquids: Are Reaction Rates Anomalously High?
journal, January 2012
- Liang, Min; Kaintz, Anne; Baker, Gary A.
- The Journal of Physical Chemistry B, Vol. 116, Issue 4
Ionic-liquid materials for the electrochemical challenges of the future
journal, July 2009
- Armand, Michel; Endres, Frank; MacFarlane, Douglas R.
- Nature Materials, Vol. 8, Issue 8, p. 621-629
Outer-sphere electron transfer in polar solvents
journal, July 1980
- Zusman, L. D.
- Chemical Physics, Vol. 49, Issue 2
On the Theory of Oxidation‐Reduction Reactions Involving Electron Transfer. I
journal, May 1956
- Marcus, R. A.
- The Journal of Chemical Physics, Vol. 24, Issue 5
Electrostatic Free Energy and Other Properties of States Having Nonequilibrium Polarization. I
journal, May 1956
- Marcus, R. A.
- The Journal of Chemical Physics, Vol. 24, Issue 5
Electrochemical Characterization of 1-Ethyl-3-methylimidazolium Thiocyanate and Measurement of Triiodide Diffusion Coefficients in Blends of two Ionic Liquids
journal, January 2008
- Zistler, M.; Schreiner, C.; Wachter, P.
- International Journal of Electrochemical Science, Vol. 3, Issue 3
Adiabatic Electron Transfer in a Room-Temperature Ionic Liquid: Reaction Dynamics and Kinetics
journal, October 2009
- Shim, Youngseon; Kim, Hyung J.
- The Journal of Physical Chemistry B, Vol. 113, Issue 39
Electron transfers in chemistry and biology
journal, August 1985
- Marcus, R. A.; Sutin, Norman
- Biochimica et Biophysica Acta (BBA) - Reviews on Bioenergetics, Vol. 811, Issue 3
Time-Dependent Rate Coefficients for Diffusion-Influenced Reactions with Centrosymmetric Potentials
journal, March 2005
- Dudko, Olga K.; Szabo, Attila
- The Journal of Physical Chemistry B, Vol. 109, Issue 12
Viscosity of (C2–C14) 1-alkyl-3-methylimidazolium bis(trifluoromethylsulfonyl)amide ionic liquids in an extended temperature range
journal, February 2011
- Tariq, Mohammad; Carvalho, Pedro J.; Coutinho, João A. P.
- Fluid Phase Equilibria, Vol. 301, Issue 1
Free Energy of Nonequilibrium Polarization Systems. II. Homogeneous and Electrode Systems
journal, April 1963
- Marcus, R. A.
- The Journal of Chemical Physics, Vol. 38, Issue 8
1-Ethyl-3-methylimidazolium Based Ionic Liquids Containing Cyano Groups: Synthesis, Characterization, and Crystal Structure
journal, February 2004
- Yoshida, Yukihiro; Muroi, Koji; Otsuka, Akihiro
- Inorganic Chemistry, Vol. 43, Issue 4
Ionic Liquids at Electrified Interfaces
journal, March 2014
- Fedorov, Maxim V.; Kornyshev, Alexei A.
- Chemical Reviews, Vol. 114, Issue 5
Computer simulation studies of electron transfer parameters for cyanoanthracene/N,N-dimethylaniline solutions
journal, March 2003
- Scherer, P. O. J.; Tachiya, M.
- The Journal of Chemical Physics, Vol. 118, Issue 9
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
journal, April 2015
- Araque, Juan C.; Yadav, Sharad K.; Shadeck, Michael
- The Journal of Physical Chemistry B, Vol. 119, Issue 23
Dynamic Stokes Shift and Excitation Wavelength Dependent Fluorescence of Dipolar Molecules in Room Temperature Ionic Liquids
journal, July 2006
- Samanta, Anunay
- The Journal of Physical Chemistry B, Vol. 110, Issue 28
Photoelectron transfer from excited-state ruthenium(ii) tris(bipyridyl) to methylviologen in an ionic liquid
journal, January 2000
- Gordon, Charles M.; McLean, Andrew J.
- Chemical Communications, Issue 15
How Does the Ionic Liquid Organizational Landscape Change when Nonpolar Cationic Alkyl Groups Are Replaced by Polar Isoelectronic Diethers?
journal, January 2013
- Kashyap, Hemant K.; Santos, Cherry S.; Daly, Ryan P.
- The Journal of Physical Chemistry B, Vol. 117, Issue 4
Electrochemical Reactivity in Room-Temperature Ionic Liquids
journal, July 2008
- Hapiot, Philippe; Lagrost, Corinne
- Chemical Reviews, Vol. 108, Issue 7
Theory of diffusion-influenced fluorescence quenching
journal, September 1989
- Szabo, Attila
- The Journal of Physical Chemistry, Vol. 93, Issue 19
Spurious Observation of the Marcus Inverted Region in Bimolecular Photoinduced Electron Transfer
journal, July 2012
- Rosspeintner, Arnulf; Koch, Marius; Angulo, Gonzalo
- Journal of the American Chemical Society, Vol. 134, Issue 28
Physical trends and structural features in organic salts of the thiocyanate anion
journal, October 2002
- Pringle, Jennifer M.; Golding, Jake; Forsyth, Craig M.
- Journal of Materials Chemistry, Vol. 12, Issue 12
Photoinduced Electron-Transfer Reactions in Two Room-Temperature Ionic Liquids: 1-Butyl-3-methylimidazolium Hexafluorophosphate and 1-Octyl-3-methylimidazolium Hexafluorophosphate †
journal, May 2007
- Vieira, Rebecca C.; Falvey, Daniel E.
- The Journal of Physical Chemistry B, Vol. 111, Issue 18
Experimental Evidence of the Relevance of Orientational Correlations in Photoinduced Bimolecular Reactions in Solution
journal, August 2013
- Angulo, Gonzalo; Cuetos, Alejandro; Rosspeintner, Arnulf
- The Journal of Physical Chemistry A, Vol. 117, Issue 36
Excitation Wavelength Dependence of the Dynamics of Bimolecular Photoinduced Electron Transfer Reactions
journal, April 2014
- Letrun, Romain; Vauthey, Eric
- The Journal of Physical Chemistry Letters, Vol. 5, Issue 10
A Study of the Time-Resolved Fluorescence Spectrum and Red Edge Effect of ANF in a Room-Temperature Ionic Liquid
journal, June 2006
- Hu, Zhonghan; Margulis, Claudio J.
- The Journal of Physical Chemistry B, Vol. 110, Issue 23
Influence of Diffusion on the Kinetics of Donor−Acceptor Electron Transfer Monitored by the Quenching of Donor Fluorescence
journal, August 2002
- Gladkikh, V. S.; Burshtein, A. I.; Tavernier, H. L.
- The Journal of Physical Chemistry A, Vol. 106, Issue 30
Application of 1-ethyl-3-methylimidazolium thiocyanate to the electrolyte of electrochemical double layer capacitors
journal, November 2006
- Sun, Guo-hua; Li, Kai-xi; Sun, Cheng-gong
- Journal of Power Sources, Vol. 162, Issue 2
Electron-Transfer Dynamics for a Donor–Bridge–Acceptor Complex in Ionic Liquids
journal, July 2015
- DeVine, Jessalyn A.; Labib, Marena; Harries, Megan E.
- The Journal of Physical Chemistry B, Vol. 119, Issue 34
Dielectric Relaxation and Solvation Dynamics in a Prototypical Ionic Liquid + Dipolar Protic Liquid Mixture: 1-Butyl-3-Methylimidazolium Tetrafluoroborate + Water
journal, June 2013
- Zhang, Xin-Xing; Liang, Min; Hunger, Johannes
- The Journal of Physical Chemistry B, Vol. 117, Issue 49
Ionic Liquids in Electrochemical Devices and Processes: Managing Interfacial Electrochemistry
journal, November 2007
- MacFarlane, Douglas R.; Forsyth, Maria; Howlett, Patrick C.
- Accounts of Chemical Research, Vol. 40, Issue 11
Interactions between water and 1-butyl-1-methylpyrrolidinium ionic liquids
journal, August 2015
- Fadeeva, Tatiana A.; Husson, Pascale; DeVine, Jessalyn A.
- The Journal of Chemical Physics, Vol. 143, Issue 6
Molecular volumes and the Stokes-Einstein equation
journal, April 1970
- Edward, John T.
- Journal of Chemical Education, Vol. 47, Issue 4
Solvent-Controlled Intramolecular Electron Transfer in Ionic Liquids
journal, May 2011
- Li, Xiang; Liang, Min; Chakraborty, Anjan
- The Journal of Physical Chemistry B, Vol. 115, Issue 20
Exact calculation of the solvation energy of a pair of ions in polar media within the framework of the dielectric continuum model
journal, November 1998
- Miyazaki, Kunimasa; Tachiya, M.
- The Journal of Chemical Physics, Vol. 109, Issue 17
A Comparison of Electron-Transfer Dynamics in Ionic Liquids and Neutral Solvents
journal, February 2012
- Lee, Heather Y.; Issa, Joseph B.; Isied, Stephan S.
- The Journal of Physical Chemistry C, Vol. 116, Issue 8
A Comparative Electrochemical Study of Diffusion in Room Temperature Ionic Liquid Solvents versus Acetonitrile
journal, March 2005
- Evans, Russell G.; Klymenko, Oleksiy V.; Price, Paul D.
- ChemPhysChem, Vol. 6, Issue 3
High-Pressure Testing of Heterogeneous Charge Transfer in a Room-Temperature Ionic Liquid: Evidence for Solvent Dynamic Control
journal, March 2008
- Dolidze, Tina D.; Khoshtariya, Dimitri E.; Illner, Peter
- The Journal of Physical Chemistry B, Vol. 112, Issue 10
Controlling the Outcome of Electron Transfer Reactions in Ionic Liquids
journal, September 2009
- Annapureddy, Harsha V. R.; Margulis, Claudio J.
- The Journal of Physical Chemistry B, Vol. 113, Issue 35
Bimolecular Photoinduced Electron Transfer in Imidazolium-Based Room-Temperature Ionic Liquids Is Not Faster than in Conventional Solvents
journal, February 2012
- Koch, Marius; Rosspeintner, Arnulf; Angulo, Gonzalo
- Journal of the American Chemical Society, Vol. 134, Issue 8
Communication: Unusual structure and transport in ionic liquid-hexane mixtures
journal, March 2015
- Liang, Min; Khatun, Sufia; Castner, Edward W.
- The Journal of Chemical Physics, Vol. 142, Issue 12
Lifetimes of Radical Anions of Dicyanoanthracene, Phenazine, and Anthraquinone in the Excited State from the Selective Electron-Transfer Quenching
journal, January 1996
- Fujita, Morifumi; Ishida, Akito; Majima, Tetsuro
- The Journal of Physical Chemistry, Vol. 100, Issue 13
Solute Diffusion in Ionic Liquids, NMR Measurements and Comparisons to Conventional Solvents
journal, September 2013
- Kaintz, Anne; Baker, Gary; Benesi, Alan
- The Journal of Physical Chemistry B, Vol. 117, Issue 39
On the Theory of Electron‐Transfer Reactions. VI. Unified Treatment for Homogeneous and Electrode Reactions
journal, July 1965
- Marcus, R. A.
- The Journal of Chemical Physics, Vol. 43, Issue 2
Energy applications of ionic liquids
journal, January 2009
- Wishart, James F.
- Energy & Environmental Science, Vol. 2, Issue 9
Ionic Liquids: Structure and Photochemical Reactions
journal, May 2011
- Castner, Edward W.; Margulis, Claudio J.; Maroncelli, Mark
- Annual Review of Physical Chemistry, Vol. 62, Issue 1
Solute–solute spatial distribution in hydrogen bonding liquids probed with time-dependent intermolecular electron transfer
journal, January 2001
- Tavernier, H. L.; Fayer, M. D.
- The Journal of Chemical Physics, Vol. 114, Issue 10
Solvent as Electron Donor: Donor/Acceptor Electronic Coupling Is a Dynamical Variable
journal, March 2000
- Castner, Edward W.; Kennedy, Darcy; Cave, Robert J.
- The Journal of Physical Chemistry A, Vol. 104, Issue 13
Fluorescence Response of 4-( N , N ′-Dimethylamino)benzonitrile in Room Temperature Ionic Liquids: Observation of Photobleaching under Mild Excitation Condition and Multiphoton Confocal Microscopic Study of the Fluorescence Recovery Dynamics
journal, January 2010
- Santhosh, Kotni; Banerjee, Sanghamitra; Rangaraj, Nandini
- The Journal of Physical Chemistry B, Vol. 114, Issue 5
Solubility of CO2 in ionic liquids containing cyanide anions: [c2mim][SCN], [c2mim][N(CN)2], [c2mim][C(CN)3]
journal, April 2014
- Kim, Ji Eun; Kim, Hak Joo; Lim, Jong Sung
- Fluid Phase Equilibria, Vol. 367
Morphology and intermolecular dynamics of 1-alkyl-3-methylimidazolium bis{(trifluoromethane)sulfonyl}amide ionic liquids: structural and dynamic evidence of nanoscale segregation
journal, September 2009
- Russina, Olga; Triolo, Alessandro; Gontrani, Lorenzo
- Journal of Physics: Condensed Matter, Vol. 21, Issue 42
Ultrafast Structure and Dynamics in Ionic Liquids: 2D-IR Spectroscopy Probes the Molecular Origin of Viscosity
journal, April 2014
- Ren, Zhe; Ivanova, Anna S.; Couchot-Vore, Duane
- The Journal of Physical Chemistry Letters, Vol. 5, Issue 9
Photoinduced Intermolecular Electron Transfer in Liquid Solutions
journal, July 2004
- Saik, V. O.; Goun, A. A.; Nanda, J.
- The Journal of Physical Chemistry A, Vol. 108, Issue 32
Structure of 1-Alkyl-1-methylpyrrolidinium Bis(trifluoromethylsulfonyl)amide Ionic Liquids with Linear, Branched, and Cyclic Alkyl Groups
journal, July 2013
- Kashyap, Hemant K.; Santos, Cherry S.; Murthy, N. Sanjeeva
- The Journal of Physical Chemistry B, Vol. 117, Issue 49
Dynamic solvent effects on outer‐sphere electron transfer
journal, August 1987
- Rips, Ilya; Jortner, Joshua
- The Journal of Chemical Physics, Vol. 87, Issue 4
On the Coherent Description of Diffusion-Influenced Fluorescence Quenching Experiments II: Early Events
journal, February 2010
- Angulo, Gonzalo; Kattnig, Daniel R.; Rosspeintner, Arnulf
- Chemistry - A European Journal, Vol. 16, Issue 7
Ultrafast Photochemistry in Liquids
journal, April 2013
- Rosspeintner, Arnulf; Lang, Bernhard; Vauthey, Eric
- Annual Review of Physical Chemistry, Vol. 64, Issue 1
Comparison of Diffusivity Data Derived from Electrochemical and NMR Investigations of the SeCN¯/(SeCN) 2 /(SeCN) 3 ¯ System in Ionic Liquids
journal, June 2011
- Solangi, Amber; Bond, Alan M.; Burgar, Iko
- The Journal of Physical Chemistry B, Vol. 115, Issue 21
Electrochemical Stability of Imidazolium Based Ionic Liquids Containing Cyano Groups in the Anion: A Cyclic Voltammetry, XPS and DFT Study
journal, January 2012
- Weingarth, Daniel; Czekaj, Izabela; Fei, Zhaofu
- Journal of The Electrochemical Society, Vol. 159, Issue 7
Universality of Viscosity Dependence of Translational Diffusion Coefficients of Carbon Monoxide, Diphenylacetylene, and Diphenylcyclopropenone in Ionic Liquids under Various Conditions
journal, June 2015
- Kimura, Y.; Kida, Y.; Matsushita, Y.
- The Journal of Physical Chemistry B, Vol. 119, Issue 25
A Solvent-Free, SeCN - /(SeCN) 3 - Based Ionic Liquid Electrolyte for High-Efficiency Dye-Sensitized Nanocrystalline Solar Cells
journal, June 2004
- Wang, Peng; Zakeeruddin, Shaik M.; Moser, Jacques-E.
- Journal of the American Chemical Society, Vol. 126, Issue 23
Low viscosity ionic liquids based on organic salts of the dicyanamide anion
journal, January 2001
- MacFarlane, Douglas R.; Golding, Jake; Forsyth, Stewart
- Chemical Communications, Issue 16
Ionic Liquids Based on Polynitrile Anions: Hydrophobicity, Low Proton Affinity, and High Radiolytic Resistance Combined
journal, May 2013
- Shkrob, Ilya A.; Marin, Timothy W.; Wishart, James F.
- The Journal of Physical Chemistry B, Vol. 117, Issue 23
Fast Calculation of van der Waals Volume as a Sum of Atomic and Bond Contributions and Its Application to Drug Compounds
journal, September 2003
- Zhao, Yuan H.; Abraham, Michael H.; Zissimos, Andreas M.
- The Journal of Organic Chemistry, Vol. 68, Issue 19
Diffusion‐controlled electron transfer reactions: Subpicosecond fluorescence measurements of coumarin 1 quenched by aniline and N , N ‐dimethylaniline
journal, October 1995
- Shannon, Colman F.; Eads, Daniel D.
- The Journal of Chemical Physics, Vol. 103, Issue 13
Physicochemical Properties and Structures of Room Temperature Ionic Liquids. 2. Variation of Alkyl Chain Length in Imidazolium Cation
journal, April 2005
- Tokuda, Hiroyuki; Hayamizu, Kikuko; Ishii, Kunikazu
- The Journal of Physical Chemistry B, Vol. 109, Issue 13
Cation/Anion Associations in Ionic Liquids Modulated by Hydration and Ionic Medium
journal, April 2011
- Hou, Jianbo; Zhang, Zhiyang; Madsen, Louis A.
- The Journal of Physical Chemistry B, Vol. 115, Issue 16
Complete Solvation Response of Coumarin 153 in Ionic Liquids
journal, August 2012
- Zhang, Xin-Xing; Liang, Min; Ernsting, Nikolaus P.
- The Journal of Physical Chemistry B, Vol. 117, Issue 16
Photoinduced intermolecular electron transfer in complex liquids: Experiment and theory
journal, December 2000
- Tavernier, H. L.; Kalashnikov, M. M.; Fayer, M. D.
- The Journal of Chemical Physics, Vol. 113, Issue 22
Distance Dependence of Electron Transfer in DNA: The Role of the Reorganization Energy and Free Energy
journal, December 2000
- Tavernier, H. L.; Fayer, M. D.
- The Journal of Physical Chemistry B, Vol. 104, Issue 48
Photoinduced Electron Transfer Reaction in Room Temperature Ionic Liquids: A Combined Laser Flash Photolysis and Fluorescence Study
journal, March 2007
- Paul, Aniruddha; Samanta, Anunay
- The Journal of Physical Chemistry B, Vol. 111, Issue 8
A subpicosecond, subnanosecond and steady‐state study of diffusion‐influenced fluorescence quenching
journal, July 1990
- Eads, Daniel D.; Dismer, Berit G.; Fleming, Graham R.
- The Journal of Chemical Physics, Vol. 93, Issue 2