Building and testing correlations for the estimation of one-electron reduction potentials of a diverse set of organic molecules: ESTIMATING ONE-ELECTRON REDUCTION POTENTIALS

Méndez-Hernández, Dalvin D.; Gillmore, Jason G.; Montano, Luis A.; Gust, Devens; Moore, Thomas A.; Moore, Ana L.; Mujica, Vladimiro

doi:10.1002/poc.3413

Title: Building and testing correlations for the estimation of one-electron reduction potentials of a diverse set of organic molecules: ESTIMATING ONE-ELECTRON REDUCTION POTENTIALS

Journal Article · Thu Jan 29 00:00:00 EST 2015 · Journal of Physical Organic Chemistry

DOI:https://doi.org/10.1002/poc.3413· OSTI ID:1385937

Méndez-Hernández, Dalvin D. ^[1]; Gillmore, Jason G. ^[2]; Montano, Luis A. ^[1]; Gust, Devens ^[1]; Moore, Thomas A. ^[1]; Moore, Ana L. ^[1]; Mujica, Vladimiro ^[1]

Center for Bio-Inspired Solar Fuel Production, Department of Chemistry and Biochemistry, Arizona State University, Tempe AZ 85287-1604 USA
Center for Bio-Inspired Solar Fuel Production, Department of Chemistry and Biochemistry, Arizona State University, Tempe AZ 85287-1604 USA; Department of Chemistry, Hope College, Holland MI 49423 USA

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Research Organization:: Energy Frontier Research Centers (EFRC) (United States). Center for Bio-Inspired Solar Fuel Production (BISfuel)

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

DOE Contract Number:: SC0001016

OSTI ID:: 1385937

Journal Information:: Journal of Physical Organic Chemistry, Vol. 28, Issue 5; Related Information: BISfuel partners with Arizona State University.; ISSN 0894-3230

Country of Publication:: United States

Language:: English

References (48)

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
Higher fullerenes as electron acceptors for polymer solar cells: A quantum chemical study Morvillo, P. Solar Energy Materials and Solar Cells, Vol. 93, Issue 10 https://doi.org/10.1016/j.solmat.2009.06.016	journal	October 2009
Experimental and Computed Absolute Redox Potentials of Polycyclic Aromatic Hydrocarbons are Highly Linearly Correlated Over a Wide Range of Structures and Potentials Davis, Anthony P.; Fry, Albert J. The Journal of Physical Chemistry A, Vol. 114, Issue 46 https://doi.org/10.1021/jp106088n	journal	November 2010
Determination of Redox Potentials for the Watson−Crick Base Pairs, DNA Nucleosides, and Relevant Nucleoside Analogues Crespo-Hernández, Carlos E.; Close, David M.; Gorb, Leonid The Journal of Physical Chemistry B, Vol. 111, Issue 19 https://doi.org/10.1021/jp0684224	journal	May 2007
Tuning the HOMO and LUMO Energy Levels of Organic Chromophores for Dye Sensitized Solar Cells Hagberg, Daniel P.; Marinado, Tannia; Karlsson, Karl Martin The Journal of Organic Chemistry, Vol. 72, Issue 25 https://doi.org/10.1021/jo701592x	journal	December 2007
Electrochemical and density functional theory modeled reduction of enolized 1,3-diketones Kuhn, Annemarie; von Eschwege, Karel G.; Conradie, Jeanet Electrochimica Acta, Vol. 56, Issue 17 https://doi.org/10.1016/j.electacta.2011.03.083	journal	July 2011
Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density Lee, Chengteh; Yang, Weitao; Parr, Robert G. Physical Review B, Vol. 37, Issue 2 https://doi.org/10.1103/PhysRevB.37.785	journal	January 1988
The influence of polarization functions on molecular orbital hydrogenation energies Hariharan, P. C.; Pople, J. A. Theoretica Chimica Acta, Vol. 28, Issue 3 https://doi.org/10.1007/BF00533485	journal	January 1973
The effect of d-functions on molecular orbital energies for hydrocarbons Hariharan, P. C.; Pople, J. A. Chemical Physics Letters, Vol. 16, Issue 2 https://doi.org/10.1016/0009-2614(72)80259-8	journal	October 1972
Functionalizing molecular wires: a tunable class of α,ω-diphenyl-μ,ν-dicyano-oligoenes Meisner, Jeffrey S.; Sedbrook, Danielle F.; Krikorian, Markrete Chemical Science, Vol. 3, Issue 4 https://doi.org/10.1039/c2sc00770c	journal	January 2012
Computational electrochemistry: prediction of liquid-phase reduction potentials Marenich, Aleksandr V.; Ho, Junming; Coote, Michelle L. Phys. Chem. Chem. Phys., Vol. 16, Issue 29 https://doi.org/10.1039/C4CP01572J	journal	January 2014
Spectral Characteristics and Photosensitization of TiO ₂ Nanoparticles in Reverse Micelles by Perylenes Hernández, Laura I.; Godin, Robert; Bergkamp, Jesse J. The Journal of Physical Chemistry B, Vol. 117, Issue 16 https://doi.org/10.1021/jp3086792	journal	November 2012
An improved correlation between polarographic reduction potential and huckel lumo energy. Application to non-benzenoid hydrocarbons Fry, Albert J.; Fox, Peter C. Tetrahedron, Vol. 42, Issue 19 https://doi.org/10.1016/S0040-4020(01)82074-3	journal	January 1986
Quantum chemical studies on the corrosion inhibition of some sulphonamides on mild steel in acidic medium Arslan, Taner; Kandemirli, Fatma; Ebenso, Eno E. Corrosion Science, Vol. 51, Issue 1 https://doi.org/10.1016/j.corsci.2008.10.016	journal	January 2009
Inverse Design and Synthesis of acac-Coumarin Anchors for Robust TiO ₂ Sensitization Xiao, Dequan; Martini, Lauren A.; Snoeberger, Robert C. Journal of the American Chemical Society, Vol. 133, Issue 23 https://doi.org/10.1021/ja2020313	journal	June 2011
A theoretical study of electrical and electrochemical properties of dicyanomethylene derivatives of squaric acid Xue, Zhao-Ming; Liu, Bing; Chen, Chun-Hua Electrochimica Acta, Vol. 51, Issue 21 https://doi.org/10.1016/j.electacta.2005.12.035	journal	June 2006
Theoretical studies on oxidation potentials of organophosphorus compounds Shi, Jing; Zhao, Yuan-Long; Wang, Hua-Jing Journal of Molecular Structure: THEOCHEM, Vol. 902, Issue 1-3 https://doi.org/10.1016/j.theochem.2009.02.014	journal	May 2009
Detailed analysis and follow-up studies of a high-throughput screening for indoleamine 2,3-dioxygenase 1 (IDO1) inhibitors Röhrig, Ute F.; Majjigapu, Somi Reddy; Chambon, Marc European Journal of Medicinal Chemistry, Vol. 84 https://doi.org/10.1016/j.ejmech.2014.06.078	journal	September 2014
Formal Redox Potentials of Organic Molecules in Ionic Liquids on the Basis of Quaternary Nitrogen Cations as Adiabatic Electron Affinities Seto, Kunimasa; Nakayama, Tatsushi; Uno, Bunji The Journal of Physical Chemistry B, Vol. 117, Issue 37 https://doi.org/10.1021/jp402457k	journal	September 2013
Effect of transannular interaction on the redox-potentials in a series of bicyclic quinones Sereda, Grigoriy; Van Heukelom, Jesse; Koppang, Miles Beilstein Journal of Organic Chemistry, Vol. 2 https://doi.org/10.1186/1860-5397-2-26	journal	January 2006
Reduction Potentials of Conjugated Systems Maccoll, Allan Nature, Vol. 163, Issue 4135 https://doi.org/10.1038/163178a0	journal	January 1949
Quantum Calculation of Molecular Energies and Energy Gradients in Solution by a Conductor Solvent Model Barone, Vincenzo; Cossi, Maurizio The Journal of Physical Chemistry A, Vol. 102, Issue 11 https://doi.org/10.1021/jp9716997	journal	March 1998
Reduction of Systematic Uncertainty in DFT Redox Potentials of Transition-Metal Complexes Konezny, Steven J.; Doherty, Mark D.; Luca, Oana R. The Journal of Physical Chemistry C, Vol. 116, Issue 10 https://doi.org/10.1021/jp300485t	journal	March 2012
Photophysical, Spectroscopic, and Computational Studies of a Series of Re(I) Tricarbonyl Complexes Containing 2,6-Dimethylphenylisocyanide and 5- and 6-Derivatized Phenanthroline Ligands Villegas, John M.; Stoyanov, Stanislav R.; Huang, Wei Inorganic Chemistry, Vol. 44, Issue 7 https://doi.org/10.1021/ic048786f	journal	April 2005
Redox Properties of Organofullerenes Suzuki, Toshiyasu; Maruyama, Yusei; Akasaka, Takeshi Journal of the American Chemical Society, Vol. 116, Issue 4 https://doi.org/10.1021/ja00083a022	journal	February 1994
Substituent Effect on the Meso-Substituted Porphyrins: Theoretical Screening of Sensitizer Candidates for Dye-Sensitized Solar Cells Ma, Ruimin; Guo, Ping; Cui, Hongji The Journal of Physical Chemistry A, Vol. 113, Issue 37 https://doi.org/10.1021/jp905412y	journal	September 2009
Optical, Redox, and NLO Properties of Tricyanovinyl Oligothiophenes: Comparisons between Symmetric and Asymmetric Substitution Patterns Casado, Juan; Ruiz Delgado, M. Carmen; Rey Merchán, M. Carmen Chemistry - A European Journal, Vol. 12, Issue 21 https://doi.org/10.1002/chem.200501389	journal	July 2006
Accelerated computational discovery of high-performance materials for organic photovoltaics by means of cheminformatics Olivares-Amaya, Roberto; Amador-Bedolla, Carlos; Hachmann, Johannes Energy & Environmental Science, Vol. 4, Issue 12 https://doi.org/10.1039/c1ee02056k	journal	January 2011
Computational modeling of standard reduction potentials of B ₁₂ cofactors Kumar, Manoj; Galezowski, Wlodzimierz; Kozlowski, Pawel M. International Journal of Quantum Chemistry, Vol. 113, Issue 4 https://doi.org/10.1002/qua.24155	journal	May 2012
Tetrakis(thiadiazole)porphyrazines. 5. Electrochemical and DFT/TDDFT Studies of the Free-Base Macrocycle and Its Mg ^II , Zn ^II , and Cu ^II Complexes Donzello, Maria Pia; Ercolani, Claudio; Kadish, Karl M. Inorganic Chemistry, Vol. 46, Issue 10 https://doi.org/10.1021/ic070038d	journal	May 2007
Efficient Computational Methods for Accurately Predicting Reduction Potentials of Organic Molecules Speelman, Amy L.; Gillmore, Jason G. The Journal of Physical Chemistry A, Vol. 112, Issue 25 https://doi.org/10.1021/jp800782e	journal	June 2008
One-Electron and Two-Electron Transfers in Electrochemistry and Homogeneous Solution Reactions Evans, Dennis H. Chemical Reviews, Vol. 108, Issue 7 https://doi.org/10.1021/cr068066l	journal	July 2008
Expanding and Testing a Computational Method for Predicting the Ground State Reduction Potentials of Organic Molecules on the Basis of Empirical Correlation to Experiment Lynch, Eugene J.; Speelman, Amy L.; Curry, Bryce A. The Journal of Organic Chemistry, Vol. 77, Issue 15 https://doi.org/10.1021/jo300853k	journal	July 2012
Accurate Calculation of Absolute One-Electron Redox Potentials of Some para -Quinone Derivatives in Acetonitrile Namazian, Mansoor; Coote, Michelle L. The Journal of Physical Chemistry A, Vol. 111, Issue 30 https://doi.org/10.1021/jp0725883	journal	August 2007
DFT Study on the Standard Electrode Potentials of Imidazole, Tetrathiafulvalene, and Tetrathiafulvalene−Imidazole Tugsuz, Tugba The Journal of Physical Chemistry B, Vol. 114, Issue 51 https://doi.org/10.1021/jp106705d	journal	December 2010
Self‐consistent molecular orbital methods. XXIII. A polarization‐type basis set for second‐row elements Francl, Michelle M.; Pietro, William J.; Hehre, Warren J. The Journal of Chemical Physics, Vol. 77, Issue 7, p. 3654-3665 https://doi.org/10.1063/1.444267	journal	October 1982
Prediction of initial reduction potentials of compounds related to anthracyclines and implications for estimating cardiotoxicity Kawakami, Y.; Hopfinger, A. J. Chemical Research in Toxicology, Vol. 3, Issue 3 https://doi.org/10.1021/tx00015a009	journal	May 1990
Molecular Engineering of Organic Sensitizers for Dye-Sensitized Solar Cell Applications Hagberg, Daniel P.; Yum, Jun-Ho; Lee, HyoJoong Journal of the American Chemical Society, Vol. 130, Issue 19 https://doi.org/10.1021/ja800066y	journal	May 2008
Correlation between the redox potentials of 9-substituted anthracenes and the results of PM3 calculation Okazaki, Satoshi; Oyarna, Munetaka; Nomura, Satoshi Electroanalysis, Vol. 9, Issue 16 https://doi.org/10.1002/elan.1140091605	journal	November 1997
Redox properties of non-alternant cyclopenta-fused polycyclic aromatic hydrocarbons: The effect of peripheral pentagon annelation Koper, Carola; Sarobe, Martin; Jenneskens, Leonardus W. Phys. Chem. Chem. Phys., Vol. 6, Issue 2 https://doi.org/10.1039/B312234D	journal	January 2004
Über die Zuordnung von Wellenfunktionen und Eigenwerten zu den Einzelnen Elektronen Eines Atoms Koopmans, T. Physica, Vol. 1, Issue 1-6 https://doi.org/10.1016/S0031-8914(34)90011-2	journal	January 1934
Simple and accurate correlation of experimental redox potentials and DFT-calculated HOMO/LUMO energies of polycyclic aromatic hydrocarbons Méndez-Hernández, Dalvin D.; Tarakeshwar, Pilarisetty; Gust, Devens Journal of Molecular Modeling, Vol. 19, Issue 7 https://doi.org/10.1007/s00894-012-1694-7	journal	December 2012
Calculation of One-Electron Redox Potentials Revisited. Is It Possible to Calculate Accurate Potentials with Density Functional Methods? Roy, Lindsay E.; Jakubikova, Elena; Guthrie, M. Graham The Journal of Physical Chemistry A, Vol. 113, Issue 24 https://doi.org/10.1021/jp811388w	journal	June 2009
Novel Zinc Porphyrin Sensitizers for Dye-Sensitized Solar Cells: Synthesis and Spectral, Electrochemical, and Photovoltaic Properties Lee, Cheng-Wei; Lu, Hsueh-Pei; Lan, Chi-Ming Chemistry - A European Journal, Vol. 15, Issue 6 https://doi.org/10.1002/chem.200801572	journal	January 2009
Reduction potential predictions of some aromatic nitrogen-containing molecules Assary, Rajeev S.; Brushett, Fikile R.; Curtiss, Larry A. RSC Adv., Vol. 4, Issue 101 https://doi.org/10.1039/C4RA08563A	journal	January 2014
Computed redox potentials and the design of bioreductive agents Reynolds, Christopher A.; King, Paul M.; Richards, W. Graham Nature, Vol. 334, Issue 6177 https://doi.org/10.1038/334080a0	journal	July 1988
Theoretical study of reduction potentials of substituted flavins Li, Xiao-Lu; Fu, Yao Journal of Molecular Structure: THEOCHEM, Vol. 856, Issue 1-3 https://doi.org/10.1016/j.theochem.2008.01.029	journal	May 2008
Energies, structures, and electronic properties of molecules in solution with the C-PCM solvation model Cossi, Maurizio; Rega, Nadia; Scalmani, Giovanni Journal of Computational Chemistry, Vol. 24, Issue 6 https://doi.org/10.1002/jcc.10189	journal	April 2003

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Title: Building and testing correlations for the estimation of one-electron reduction potentials of a diverse set of organic molecules: ESTIMATING ONE-ELECTRON REDUCTION POTENTIALS

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