Electron localization of anions probed by nitrile vibrations

Mani, Tomoyasu; Grills, David C.; Newton, Marshall D.; Miller, John R.

doi:10.1021/jacs.5b04648

Title: Electron localization of anions probed by nitrile vibrations

Journal Article · Sun Aug 02 00:00:00 EDT 2015 · Journal of the American Chemical Society

DOI:https://doi.org/10.1021/jacs.5b04648· OSTI ID:1214538

Mani, Tomoyasu ^[1]; Grills, David C. ^[1]; Newton, Marshall D. ^[1]; Miller, John R. ^[1]

Brookhaven National Lab. (BNL), Upton, NY (United States)

Localization and delocalization of electrons is a key concept in chemistry, and is one of the important factors determining the efficiency of electron transport through organic conjugated molecules, which have potential to act as “molecular wires”. This, in turn, substantially influences the efficiencies of organic solar cells and other molecular electronic devices. It is also necessary to understand the electronic energy landscape and the dynamics of electrons through molecular chain that govern their transport capabilities in one-dimensional conjugated chains so that we can better define the design principles of conjugated molecules for their applications. We show that nitrile ν(C≡N) vibrations respond to the degree of electron localization in nitrile-substituted organic anions by utilizing time-resolved infrared (TRIR) detection combined with pulse radiolysis. Measurements of a series of aryl nitrile anions allow us to construct a semi-empirical calibration curve between the changes in the ν(C≡N) IR shifts and the changes in the electronic charges from the neutral to the anion states in the nitriles; more electron localization in the nitrile anion results in larger IR shifts. Furthermore, the IR linewidth in anions can report a structural change accompanying changes in the electronic density distribution. Probing the shift of the nitrile ν(C≡N) IR vibrational bands enables us to determine how the electron is localized in anions of nitrile-functionalized oligofluorenes, considered as organic mixed-valence compounds. We estimate the diabatic electron transfer distance, electronic coupling strengths, and energy barriers in these organic mixed-valence compounds. The analysis reveals a dynamic picture, showing that the electron is moving back and forth within the oligomers with a small activation energy of ≤ k_BT, likely controlled by the movement of dihedral angles between monomer units. Thus, implications for the electron transport capability in "molecular wires" are discussed.

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:: SC00112704

OSTI ID:: 1214538

Report Number(s):: BNL-108351-2015-JA; R&D Project: CO004; KC0304030

Journal Information:: Journal of the American Chemical Society, Vol. 137, Issue 34; ISSN 0002-7863

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

Citation Metrics:

Cited by: 24 works

Citation information provided by
Web of Science

References (92)

Assessment of a long-range corrected hybrid functional Vydrov, Oleg A.; Scuseria, Gustavo E. The Journal of Chemical Physics, Vol. 125, Issue 23 https://doi.org/10.1063/1.2409292	journal	December 2006
Excited state polarizabilities of conjugated molecules calculated using time dependent density functional theory Grozema, F. C.; Telesca, R.; Jonkman, H. T. The Journal of Chemical Physics, Vol. 115, Issue 21 https://doi.org/10.1063/1.1415085	journal	December 2001
Dynamical solvent effects on activated electron-transfer reactions: principles, pitfalls, and progress Weaver, Michael J. Chemical Reviews, Vol. 92, Issue 3 https://doi.org/10.1021/cr00011a006	journal	May 1992
Estimation of Electron Transfer Distances from AM1 Calculations Nelsen, Stephen F.; Newton, Marshall D. The Journal of Physical Chemistry A, Vol. 104, Issue 44 https://doi.org/10.1021/jp002211w	journal	November 2000
Polarons, Compressed Polarons, and Bipolarons in Conjugated Polymers Bakalis, Jin; Cook, Andrew R.; Asaoka, Sadayuki The Journal of Physical Chemistry C, Vol. 118, Issue 1 https://doi.org/10.1021/jp408910a	journal	December 2013
The LEAF picosecond pulse radiolysis facility at Brookhaven National Laboratory Wishart, James F.; Cook, Andrew R.; Miller, John R. Review of Scientific Instruments, Vol. 75, Issue 11 https://doi.org/10.1063/1.1807004	journal	November 2004
STARK SPECTROSCOPY: Applications in Chemistry, Biology, and Materials Science Bublitz, Gerold U.; Boxer, Steven G. Annual Review of Physical Chemistry, Vol. 48, Issue 1 https://doi.org/10.1146/annurev.physchem.48.1.213	journal	October 1997
Electronic Structure and Optical Properties of Charged Oligofluorenes Studied by VIS/NIR Spectroscopy and Time-Dependent Density Functional Theory Fratiloiu, Silvia; Grozema, Ferdinand C.; Koizumi, Yoshiko The Journal of Physical Chemistry B, Vol. 110, Issue 12 https://doi.org/10.1021/jp055785f	journal	March 2006
Solvent dynamical effects on the electron self-exchange rate of the TEMPO˙/TEMPO + couple (TEMPO = 2,2,6,6-tetramethyl-1-piperidinyloxy radical) : Part I. ESR-linebroadening measurements at T = 298 K Grampp, Guenter; Rasmussen, Kenneth Phys. Chem. Chem. Phys., Vol. 4, Issue 22 https://doi.org/10.1039/b206313a	journal	January 2002
Calculation of electronic coupling matrix elements for ground and excited state electron transfer reactions: Comparison of the generalized Mulliken–Hush and block diagonalization methods Cave, Robert J.; Newton, Marshall D. The Journal of Chemical Physics, Vol. 106, Issue 22 https://doi.org/10.1063/1.474023	journal	June 1997
Electron-Vibrational Dynamics of Photoexcited Polyfluorenes Franco, Ignacio; Tretiak, Sergei Journal of the American Chemical Society, Vol. 126, Issue 38 https://doi.org/10.1021/ja0489285	journal	September 2004
Symmetry vs. fluxionality, a radical anion with borderline properties Mazur, Stephen; Streekumar, C.; Schroeder, Albert H. Journal of the American Chemical Society, Vol. 98, Issue 21 https://doi.org/10.1021/ja00437a056	journal	October 1976
Electronic Structures of Exciplexes and Excited Charge-Transfer Complexes Gould, Ian R.; Young, Ralph H.; Mueller, Leonard J. Journal of the American Chemical Society, Vol. 116, Issue 18 https://doi.org/10.1021/ja00097a028	journal	September 1994
Probing Ground-to-CT State Electronic Coupling for the System with No Apparent Charge Transfer Absorption Intensity by Ultrafast Visible-Pump/Mid-IR-Probe Spectroscopy Kim, Hyeong-Mook; Park, Jaeheung; Lee, Young Tak The Journal of Physical Chemistry C, Vol. 115, Issue 45 https://doi.org/10.1021/jp207122e	journal	October 2011
A state-specific polarizable continuum model time dependent density functional theory method for excited state calculations in solution Improta, Roberto; Barone, Vincenzo; Scalmani, Giovanni The Journal of Chemical Physics, Vol. 125, Issue 5 https://doi.org/10.1063/1.2222364	journal	August 2006
X-ray Structure Analysis and the Intervalent Electron Transfer in Organic Mixed-Valence Crystals with Bridged Aromatic Cation Radicals Lindeman, Sergey V.; Rosokha, Sergiy V.; Sun, Duoli Journal of the American Chemical Society, Vol. 124, Issue 5 https://doi.org/10.1021/ja011579j	journal	February 2002
Watching Electrons Move in Real Time: Ultrafast Infrared Spectroscopy of a Polymer Blend Photovoltaic Material Barbour, Larry W.; Hegadorn, Maureen; Asbury, John B. Journal of the American Chemical Society, Vol. 129, Issue 51 https://doi.org/10.1021/ja074657x	journal	December 2007
Direct approach to measuring the Franck-Condon barrier to electron transfer between metal ions Creutz, Carol; Taube, Henry Journal of the American Chemical Society, Vol. 91, Issue 14 https://doi.org/10.1021/ja01042a072	journal	July 1969
Charge Photogeneration in Organic Solar Cells Clarke, Tracey M.; Durrant, James R. Chemical Reviews, Vol. 110, Issue 11, p. 6736-6767 https://doi.org/10.1021/cr900271s	journal	November 2010
Toward effective and reliable fluorescence energies in solution by a new state specific polarizable continuum model time dependent density functional theory approach Improta, Roberto; Scalmani, Giovanni; Frisch, Michael J. The Journal of Chemical Physics, Vol. 127, Issue 7 https://doi.org/10.1063/1.2757168	journal	August 2007
Relation between the electronic structure and infrared frequencies of the cyano-group in alkali-metal complexes of some substituted benzonitriles Juchnovski, I. N.; Binev, I. G. Journal of Molecular Structure, Vol. 7, Issue 3-4 https://doi.org/10.1016/0022-2860(71)87021-7	journal	February 1971
Conjugated “Molecular Wire” for Excitons Shibano, Yuki; Imahori, Hiroshi; Sreearunothai, Paiboon The Journal of Physical Chemistry Letters, Vol. 1, Issue 9 https://doi.org/10.1021/jz100380m	journal	April 2010
Role of Bad Dihedral Angles: Methylfluorenes Act as Energy Barriers for Excitons and Polarons of Oligofluorenes Mani, Tomoyasu; Miller, John R. The Journal of Physical Chemistry A, Vol. 118, Issue 40 https://doi.org/10.1021/jp5080626	journal	September 2014
Stark Realities ^† Boxer, Steven G. The Journal of Physical Chemistry B, Vol. 113, Issue 10 https://doi.org/10.1021/jp8067393	journal	March 2009
Charge-Localized p -Phenylenedihydrazine Radical Cations: ESR and Optical Studies of Intramolecular Electron Transfer Rates Nelsen, Stephen F.; Ismagilov, Rustem F.; Powell, Douglas R. Journal of the American Chemical Society, Vol. 119, Issue 42 https://doi.org/10.1021/ja9720321	journal	October 1997
Chain-Length Dependence of the Electrochemical Properties of Conjugated Oligofluorenes Chi, Chunyan; Wegner, Gerhard Macromolecular Rapid Communications, Vol. 26, Issue 19 https://doi.org/10.1002/marc.200500437	journal	October 2005
A vibronic model for IR absorption by a mixed valence anion radical Schroeder, Albert H.; Mazur, Stephen Journal of the American Chemical Society, Vol. 100, Issue 23 https://doi.org/10.1021/ja00491a035	journal	November 1978
Adiabatic Electron Transfer: Comparison of Modified Theory with Experiment Nelsen, S. F. Science, Vol. 278, Issue 5339 https://doi.org/10.1126/science.278.5339.846	journal	October 1997
Electron Paramagnetic Resonance Spectroscopy of Bis(triarylamine) Paracyclophanes as Model Compounds for the Intermolecular Charge-Transfer in Solid State Materials for Optoelectronic Applications Kattnig, Daniel R.; Mladenova, Boryana; Grampp, Günter The Journal of Physical Chemistry C, Vol. 113, Issue 7 https://doi.org/10.1021/jp8107705	journal	January 2009
Quantum Mechanical Continuum Solvation Models Tomasi, Jacopo; Mennucci, Benedetta; Cammi, Roberto Chemical Reviews, Vol. 105, Issue 8 https://doi.org/10.1021/cr9904009	journal	August 2005
Vibrational Stark Effects To Identify Ion Pairing and Determine Reduction Potentials in Electrolyte-Free Environments Mani, Tomoyasu; Grills, David C.; Miller, John R. Journal of the American Chemical Society, Vol. 137, Issue 3 https://doi.org/10.1021/ja512302c	journal	January 2015
Determining atom-centered monopoles from molecular electrostatic potentials. The need for high sampling density in formamide conformational analysis Breneman, Curt M.; Wiberg, Kenneth B. Journal of Computational Chemistry, Vol. 11, Issue 3 https://doi.org/10.1002/jcc.540110311	journal	April 1990
Quantum-chemical insights into mixed-valence systems: within and beyond the Robin–Day scheme Parthey, M.; Kaupp, M. Chem. Soc. Rev., Vol. 43, Issue 14 https://doi.org/10.1039/c3cs60481k	journal	January 2014
The Formation and Recombination Kinetics of Positively Charged Poly(phenylene vinylene) Chains in Pulse-Irradiated Dilute Solutions Grozema, Ferdinand C.; Hoofman, Romano J. O. M.; Candeias, Luis P. The Journal of Physical Chemistry A, Vol. 107, Issue 31 https://doi.org/10.1021/jp022379c	journal	July 2003
Carbonyl Spectator Bonds as Sensitive Sensors for Charge Transfer Reactions on the Femtosecond Time Scale Volk, Martin; Gilch, Peter; Kompa, Christian The Journal of Physical Chemistry A, Vol. 104, Issue 21 https://doi.org/10.1021/jp000575i	journal	June 2000
Insights into Current Limitations of Density Functional Theory Cohen, A. J.; Mori-Sanchez, P.; Yang, W. Science, Vol. 321, Issue 5890 https://doi.org/10.1126/science.1158722	journal	August 2008
Solvent-Induced Infrared Frequency Shifts in Aromatic Nitriles Are Quantitatively Described by the Vibrational Stark Effect Levinson, Nicholas M.; Fried, Stephen D.; Boxer, Steven G. The Journal of Physical Chemistry B, Vol. 116, Issue 35 https://doi.org/10.1021/jp301054e	journal	April 2012
Distance Dependence of Electron Transfer Rates Hush, N. S. Coordination Chemistry Reviews, Vol. 64 https://doi.org/10.1016/0010-8545(85)80047-3	journal	May 1985
Electron and Hole Transport To Trap Groups at the Ends of Conjugated Polyfluorenes Asaoka, Sadayuki; Takeda, Norihiko; Iyoda, Tomokazu Journal of the American Chemical Society, Vol. 130, Issue 36 https://doi.org/10.1021/ja800426z	journal	September 2008
How intermolecular geometrical disorder affects the molecular doping of donor–acceptor copolymers Di Nuzzo, Daniele; Fontanesi, Claudio; Jones, Rebecca Nature Communications, Vol. 6, Issue 1 https://doi.org/10.1038/ncomms7460	journal	March 2015
Density‐functional thermochemistry. III. The role of exact exchange Becke, Axel D. The Journal of Chemical Physics, Vol. 98, Issue 7, p. 5648-5652 https://doi.org/10.1063/1.464913	journal	April 1993
The Degree of Charge Transfer in Ground and Charge-Separated States Revealed by Ultrafast Visible Pump/Mid-IR Probe Spectroscopy Rubtsov, Igor V.; Kang, Youn K.; Redmore, Naomi P. Journal of the American Chemical Society, Vol. 126, Issue 16 https://doi.org/10.1021/ja030674k	journal	April 2004
Organic Mixed-Valence Compounds: A Playground for Electrons and Holes Heckmann, Alexander; Lambert, Christoph Angewandte Chemie International Edition, Vol. 51, Issue 2 https://doi.org/10.1002/anie.201100944	journal	November 2011
Optical absorption from polarons in a model of polyacetylene Fesser, K.; Bishop, A. R.; Campbell, D. K. Physical Review B, Vol. 27, Issue 8 https://doi.org/10.1103/PhysRevB.27.4804	journal	April 1983
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
Recent development of push–pull conjugated polymers for bulk-heterojunction photovoltaics: rational design and fine tailoring of molecular structures Duan, Chunhui; Huang, Fei; Cao, Yong Journal of Materials Chemistry, Vol. 22, Issue 21 https://doi.org/10.1039/c2jm30470h	journal	January 2012
Giant infrared absorption bands of electrons and holes in conjugated molecules Zamadar, Matibur; Asaoka, Sadayuki; Grills, David C. Nature Communications, Vol. 4, Issue 1 https://doi.org/10.1038/ncomms3818	journal	November 2013
Electrochromism and Solvatochromism Liptay, W. Angewandte Chemie International Edition in English, Vol. 8, Issue 3 https://doi.org/10.1002/anie.196901771	journal	March 1969
Temperature Effects on Electron Transfer within Intervalence Bis(Hydrazine) Radical Cations Nelsen, Stephen F.; Ismagilov, Rustem F.; Gentile, Kevin E. Journal of the American Chemical Society, Vol. 121, Issue 30 https://doi.org/10.1021/ja984047k	journal	August 1999
Thermochromism in polyalkylthiophenes: Molecular aspects from vibrational spectroscopy Zerbi, G.; Chierichetti, B.; Ingänas, O. The Journal of Chemical Physics, Vol. 94, Issue 6 https://doi.org/10.1063/1.460593	journal	March 1991
The Localized-to-Delocalized Transition in Mixed-Valence Chemistry Demadis, Konstantinos D.; Hartshorn, Chris M.; Meyer, Thomas J. Chemical Reviews, Vol. 101, Issue 9 https://doi.org/10.1021/cr990413m	journal	September 2001
Optical transitions of symmetrical mixed-valence systems in the Class II–III transition regimeElectronic supplementary information (ESI) is available: derivation of eqn. (39c), table summarizing the relationships between band maxima and band widths predicted by the two-state model and table of spectral properties of mixed-valence ruthenium(II)/(III) bridged by pyrazine and dicyanamide. See http://www.rsc.org/suppdata/cs/b0/b008034i/ Brunschwig, Bruce S.; Creutz, Carol; Sutin, Norman Chemical Society Reviews, Vol. 31, Issue 3 https://doi.org/10.1039/b008034i	journal	April 2002
Inorganic Electron Transfer: Sharpening a Fuzzy Border in Mixed Valency and Extending Mixed Valency across Supramolecular Systems Kubiak, Clifford P. Inorganic Chemistry, Vol. 52, Issue 10 https://doi.org/10.1021/ic302331s	journal	January 2013
Charge Mobilities in Conjugated Polymers Measured by Pulse Radiolysis Time-Resolved Microwave Conductivity: From Single Chains to Solids Grozema, Ferdinand C.; Siebbeles, Laurens D. A. The Journal of Physical Chemistry Letters, Vol. 2, Issue 23 https://doi.org/10.1021/jz201229a	journal	November 2011
Photoinduced Symmetry-Breaking Charge Separation Vauthey, Eric ChemPhysChem, Vol. 13, Issue 8 https://doi.org/10.1002/cphc.201200106	journal	March 2012
Nature and Energies of Electrons and Holes in a Conjugated Polymer, Polyfluorene Takeda, Norihiko; Asaoka, Sadayuki; Miller, John R. Journal of the American Chemical Society, Vol. 128, Issue 50 https://doi.org/10.1021/ja062596h	journal	December 2006
Tests of functionals for systems with fractional electron number Vydrov, Oleg A.; Scuseria, Gustavo E.; Perdew, John P. The Journal of Chemical Physics, Vol. 126, Issue 15 https://doi.org/10.1063/1.2723119	journal	April 2007
Arylamine-Substituted Oligo(ladder-type pentaphenylene)s: Electronic Communication between Bridged Redox Centers Zhou, Gang; Baumgarten, Martin; Müllen, Klaus Journal of the American Chemical Society, Vol. 129, Issue 40 https://doi.org/10.1021/ja073148s	journal	October 2007
Constructing diabatic states from adiabatic states: Extending generalized Mulliken–Hush to multiple charge centers with Boys localization Subotnik, Joseph E.; Yeganeh, Sina; Cave, Robert J. The Journal of Chemical Physics, Vol. 129, Issue 24 https://doi.org/10.1063/1.3042233	journal	December 2008
The Class II/III Transition in Triarylamine Redox Systems Lambert, Christoph; Nöll, Gilbert Journal of the American Chemical Society, Vol. 121, Issue 37 https://doi.org/10.1021/ja991264s	journal	September 1999
Solvent Effect on Intramolecular Electron Transfer Rate of 1,3-Dinitrobenzene Radical Anion Hosoi, Haruko; Mori, Yukie; Masuda, Yuichi Chemistry Letters, Vol. 27, Issue 2 https://doi.org/10.1246/cl.1998.177	journal	February 1998
Charge-Transfer Transitions in Triarylamine Mixed-Valence Systems: A Joint Density Functional Theory and Vibronic Coupling Study Coropceanu, V.; Malagoli, M.; André, J. M. Journal of the American Chemical Society, Vol. 124, Issue 35 https://doi.org/10.1021/ja026437j	journal	September 2002
Organic Mixed Valence Hankache, Jihane; Wenger, Oliver S. Chemical Reviews, Vol. 111, Issue 8 https://doi.org/10.1021/cr100441k	journal	August 2011
Barrierless Free Carrier Formation in an Organic Photovoltaic Material Measured with Ultrafast Vibrational Spectroscopy Pensack, Ryan D.; Asbury, John B. Journal of the American Chemical Society, Vol. 131, Issue 44 https://doi.org/10.1021/ja906293q	journal	November 2009
Intramolecular Charge Transport along Isolated Chains of Conjugated Polymers: Effect of Torsional Disorder and Polymerization Defects Grozema, Ferdinand C.; van Duijnen, Piet Th.; Berlin, Yuri A. The Journal of Physical Chemistry B, Vol. 106, Issue 32 https://doi.org/10.1021/jp021114v	journal	August 2002
Binuclear complexes of ruthenium ammines Creutz, Carol.; Taube, H. Journal of the American Chemical Society, Vol. 95, Issue 4 https://doi.org/10.1021/ja00785a016	journal	February 1973
Solvent Control of Charge Localization in 11-Bond Bridged Dinitroaromatic Radical Anions Nelsen, Stephen F.; Weaver, Michael N.; Telo, João P. Journal of the American Chemical Society, Vol. 129, Issue 22 https://doi.org/10.1021/ja067088m	journal	May 2007
Charge Transport along Coiled Conjugated Polymer Chains Prins, Paulette; Grozema, Ferdinand C.; Galbrecht, Frank The Journal of Physical Chemistry C, Vol. 111, Issue 29 https://doi.org/10.1021/jp071077d	journal	July 2007
Generalization of the Mulliken-Hush treatment for the calculation of electron transfer matrix elements Cave, Robert J.; Newton, Marshall D. Chemical Physics Letters, Vol. 249, Issue 1-2 https://doi.org/10.1016/0009-2614(95)01310-5	journal	January 1996
Intramolecular Electronic Couplings in Class II/III Organic Mixed-Valence Systems of Bis(1,4-dimethoxybenzene) Yang, Juanhua; Zhang, Weiwei; Si, Yubing The Journal of Physical Chemistry B, Vol. 116, Issue 48 https://doi.org/10.1021/jp308242s	journal	November 2012
Predicting the Localized/Delocalized Character of Mixed-Valence Diquinone Radical Anions. Toward the Right Answer for the Right Reason Renz, Manuel; Kaupp, Martin The Journal of Physical Chemistry A, Vol. 116, Issue 43 https://doi.org/10.1021/jp308294r	journal	October 2012
Theoretical Investigation of the Ground and Excited States of Coumarin 151 and Coumarin 120 Cave, Robert J.; Burke, Kieron; Castner, Edward W. The Journal of Physical Chemistry A, Vol. 106, Issue 40 https://doi.org/10.1021/jp026071x	journal	October 2002
Nuclear, electronic, and frequency factors in electron transfer reactions Sutin, Norman Accounts of Chemical Research, Vol. 15, Issue 9 https://doi.org/10.1021/ar00081a002	journal	September 1982
Charge-Transfer and Energy-Transfer Processes in π-Conjugated Oligomers and Polymers: A Molecular Picture Brédas, Jean-Luc; Beljonne, David; Coropceanu, Veaceslav Chemical Reviews, Vol. 104, Issue 11 https://doi.org/10.1021/cr040084k	journal	November 2004
Intrachain Electron Transfer in Conducting Oligomers and Polymers: The Mixed Valence Approach Lacroix, Jean Christophe; Chane-Ching, Kathleen Isabelle; Maquère, Fabrice Journal of the American Chemical Society, Vol. 128, Issue 22 https://doi.org/10.1021/ja060390a	journal	June 2006
Fast localized orthonormal virtual orbitals which depend smoothly on nuclear coordinates Subotnik, Joseph E.; Dutoi, Anthony D.; Head-Gordon, Martin The Journal of Chemical Physics, Vol. 123, Issue 11 https://doi.org/10.1063/1.2033687	journal	September 2005
Structural Changes Accompanying Intramolecular Electron Transfer: Focus on Twisted Intramolecular Charge-Transfer States and Structures Grabowski, Zbigniew R.; Rotkiewicz, Krystyna; Rettig, Wolfgang Chemical Reviews, Vol. 103, Issue 10 https://doi.org/10.1021/cr940745l	journal	October 2003
Mobility of Holes in Oligo- and Polyfluorenes of Defined Lengths Bird, Matthew J.; Reid, Obadiah G.; Cook, Andrew R. The Journal of Physical Chemistry C, Vol. 118, Issue 12 https://doi.org/10.1021/jp5010874	journal	March 2014
Exciplex Formation in Bimolecular Photoinduced Electron-Transfer Investigated by Ultrafast Time-Resolved Infrared Spectroscopy Koch, Marius; Letrun, Romain; Vauthey, Eric Journal of the American Chemical Society, Vol. 136, Issue 10 https://doi.org/10.1021/ja500812u	journal	February 2014
Reduced Electronic Spaces for Modeling Donor/Acceptor Interactions ^† Cave, Robert J.; Edwards, Stephen T.; Kouzelos, J. Andrew The Journal of Physical Chemistry B, Vol. 114, Issue 45 https://doi.org/10.1021/jp102353q	journal	November 2010
Dicyanoaromatic radical anions as mixed valence species: DICYANOAROMATIC RADICAL ANIONS Moneo, Álvaro; Carvalho, M. Fernanda N. N.; Telo, João P. Journal of Physical Organic Chemistry, Vol. 25, Issue 7 https://doi.org/10.1002/poc.2905	journal	January 2012
The initial and final states of electron and energy transfer processes: Diabatization as motivated by system-solvent interactions Subotnik, Joseph E.; Cave, Robert J.; Steele, Ryan P. The Journal of Chemical Physics, Vol. 130, Issue 23 https://doi.org/10.1063/1.3148777	journal	June 2009
Development of nanosecond time-resolved infrared detection at the LEAF pulse radiolysis facility Grills, David C.; Farrington, Jaime A.; Layne, Bobby H. Review of Scientific Instruments, Vol. 86, Issue 4 https://doi.org/10.1063/1.4918728	journal	April 2015
Effects of Rapid Intramolecular Electron Transfer on Vibrational Spectra Ito, T. Science, Vol. 277, Issue 5326 https://doi.org/10.1126/science.277.5326.660	journal	August 1997
Polarons, Bipolarons, and Side-By-Side Polarons in Reduction of Oligofluorenes Zaikowski, Lori; Kaur, Parmeet; Gelfond, Claudia Journal of the American Chemical Society, Vol. 134, Issue 26 https://doi.org/10.1021/ja301494n	journal	June 2012
Ab Initio Calculation of Vibrational Absorption and Circular Dichroism Spectra Using Density Functional Force Fields Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F. The Journal of Physical Chemistry, Vol. 98, Issue 45, p. 11623-11627 https://doi.org/10.1021/j100096a001	journal	November 1994
Construction of Some Molecular Orbitals to Be Approximately Invariant for Changes from One Molecule to Another Boys, S. F. Reviews of Modern Physics, Vol. 32, Issue 2 https://doi.org/10.1103/RevModPhys.32.296	journal	April 1960
Importance of short-range versus long-range Hartree-Fock exchange for the performance of hybrid density functionals Vydrov, Oleg A.; Heyd, Jochen; Krukau, Aliaksandr V. The Journal of Chemical Physics, Vol. 125, Issue 7 https://doi.org/10.1063/1.2244560	journal	August 2006
Infrared spectral data on strong intramolecular electron interaction in some anion radicals containing CN groups Juchnovski, I. N.; Binev, I. G. Chemical Physics Letters, Vol. 12, Issue 1 https://doi.org/10.1016/0009-2614(71)80611-5	journal	December 1971
Solvent Effects on the Coexistence of Localized and Delocalized 4,4′-Dinitrotolane Radical Anion by Resonance Raman Spectroscopy Hoekstra, Ryan M.; Telo, João P.; Wu, Qin Journal of the American Chemical Society, Vol. 132, Issue 26 https://doi.org/10.1021/ja1017859	journal	June 2010
Semiconducting Polyfluorenes—Towards Reliable Structure-Property Relationships Scherf, U.; List, E. J. W. Advanced Materials, Vol. 14, Issue 7 https://doi.org/10.1002/1521-4095(20020404)14:7<477::AID-ADMA477>3.0.CO;2-9	journal	April 2002
The Chemistry of Conducting Polythiophenes McCullough, Richard D. Advanced Materials, Vol. 10, Issue 2, p. 93-116 https://doi.org/10.1002/(SICI)1521-4095(199801)10:2<93::AID-ADMA93>3.0.CO;2-F	journal	January 1998

Cited By (2)

Formation of the Charge‐Localized Dimer Radical Cation of 2‐Ethyl‐9,10‐dimethoxyanthracene in Solution Phase Choi, Jungkweon; Ahn, Doo‐Sik; Fujitsuka, Mamoru Chemistry – A European Journal, Vol. 25, Issue 21 https://doi.org/10.1002/chem.201900175	journal	March 2019
Structural origins of the electronic properties of materials via time-resolved infrared spectroscopy Munson, Kyle T.; Kennehan, Eric R.; Asbury, John B. Journal of Materials Chemistry C, Vol. 7, Issue 20 https://doi.org/10.1039/c9tc01348b	journal	January 2019

Similar Records

IR linewidth and intensity amplifications of nitrile vibrations report nuclear-electronic couplings and associated structural heterogeneity in radical anions

Journal Article · Wed Sep 22 00:00:00 EDT 2021 · Chemical Science · OSTI ID:1214538

Yan, Juchao; Wilson, Reid W.; Buck, Jason T.; +3 more

Probing Intermolecular Electron Delocalization in Dimer Radical Anions by Vibrational Spectroscopy

Journal Article · Wed Jul 05 00:00:00 EDT 2017 · Journal of Physical Chemistry. B, Condensed Matter, Materials, Surfaces, Interfaces and Biophysical Chemistry · OSTI ID:1214538

Mani, Tomoyasu; Grills, David C.

Identification of ion-pair structures in solution by vibrational stark effects

Journal Article · Mon Jan 25 00:00:00 EST 2016 · Journal of Physical Chemistry. B, Condensed Matter, Materials, Surfaces, Interfaces and Biophysical Chemistry · OSTI ID:1214538

Hack, John; Mani, Tomoyasu; Grills, David C.; +1 more

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Title: Electron localization of anions probed by nitrile vibrations

Citation Formats

References (92)

Cited By (2)

Similar Records

Related Subjects