Electronic States of 2,3-Diamino-1,4-naphthoquinone and Its N-Alkylated Derivatives

Wen, Jin; Turowski, Michał; Dron, Paul I.; Chalupský, Jakub; Grotjahn, Robin; Maier, Toni M.; Fatur, Steven M.; Havlas, Zdeněk; Johnson, Justin C.; Kaupp, Martin; Michl, Josef

doi:10.1021/acs.jpcc.9b08955

Title: Electronic States of 2,3-Diamino-1,4-naphthoquinone and Its N-Alkylated Derivatives

Journal Article · Wed Nov 13 00:00:00 EST 2019 · Journal of Physical Chemistry. C

DOI:https://doi.org/10.1021/acs.jpcc.9b08955· OSTI ID:1595567

Wen, Jin ^[1]; Turowski, Michał ^[2]; Dron, Paul I. ^[2]; Chalupský, Jakub ^[1];

^[3];

^[2]; Havlas, Zdeněk ^[1];

^[4];

^[3];

^[5]

Inst. of Organic Chemistry and Biochemistry, Prague (Czech Republic)
Univ. of Colorado, Boulder, CO (United States)
Technische Univ. Berlin (Germany)
National Renewable Energy Lab. (NREL), Golden, CO (United States)
Inst. of Organic Chemistry and Biochemistry, Prague (Czech Republic); Univ. of Colorado, Boulder, CO (United States)

Diaminoquinones with a captodatively stabilized biradicaloid structure are candidates for singlet fission, but few such compounds are known. We report the solution spectroscopy and photophysics of 1,2,2,3-tetramethyl-2,3-dihydro-1H-naphtho[2,3-d]imidazole-4,9-dione (1): its steady-state and transient UV–visible absorption, linear dichroism in stretched poly(vinyl alcohol), and magnetic circular dichroism. We also describe the absorption spectra of the stable radical ions 1•+ and 1•– and of two parent structures, 2,3-diamino-1,4-naphthoquinone (2) and 2,3-bis(methylamino)-1,4-naphthoquinone (3). The spectra are interpreted and electronic transitions are assigned by comparison with the results of density functional theory and MS-CASPT2 calculations.

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Research Organization:: National Renewable Energy Laboratory (NREL), Golden, CO (United States); Univ. of Colorado, Boulder, CO (United States)

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

Grant/Contract Number:: AC36-08GO28308; SC0007004

OSTI ID:: 1595567

Alternate ID(s):: OSTI ID: 1688409

Report Number(s):: NREL/JA-5900-74492; TRN: US2100663

Journal Information:: Journal of Physical Chemistry. C, Vol. 124, Issue 1; ISSN 1932-7447

Publisher:: American Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 11 works

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References (37)

Singlet Fission Smith, Millicent B.; Michl, Josef Chemical Reviews, Vol. 110, Issue 11 https://doi.org/10.1021/cr1002613	journal	November 2010
Recent Advances in Singlet Fission Smith, Millicent B.; Michl, Josef Annual Review of Physical Chemistry, Vol. 64, Issue 1 https://doi.org/10.1146/annurev-physchem-040412-110130	journal	April 2013
Detailed Balance Limit of Efficiency of p‐n Junction Solar Cells Shockley, William; Queisser, Hans J. Journal of Applied Physics, Vol. 32, Issue 3, p. 510-519 https://doi.org/10.1063/1.1736034	journal	March 1961
Solar conversion efficiency of photovoltaic and photoelectrolysis cells with carrier multiplication absorbers Hanna, M. C.; Nozik, A. J. Journal of Applied Physics, Vol. 100, Issue 7 https://doi.org/10.1063/1.2356795	journal	October 2006
Singlet Fission for Dye-Sensitized Solar Cells: Can a Suitable Sensitizer Be Found? Paci, Irina; Johnson, Justin C.; Chen, Xudong Journal of the American Chemical Society, Vol. 128, Issue 51 https://doi.org/10.1021/ja063980h	journal	December 2006
Guidance for Mutual Disposition of Chromophores for Singlet Fission Havlas, Zdenek; Michl, Josef Israel Journal of Chemistry, Vol. 56, Issue 1 https://doi.org/10.1002/ijch.201500054	journal	October 2015
Singlet Fission: Optimization of Chromophore Dimer Geometry Buchanan, Eric A.; Havlas, Zdeněk; Michl, Josef Advances in Quantum Chemistry https://doi.org/10.1016/bs.aiq.2017.03.005	book	May 2017
Captodatively Stabilized Biradicaloids as Chromophores for Singlet Fission Wen, Jin; Havlas, Zdenĕk; Michl, Josef Journal of the American Chemical Society, Vol. 137, Issue 1 https://doi.org/10.1021/ja5070476	journal	December 2014
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
Redox Behavior of 2,3-Diamino-1,4-naphthoquinone and its N -Alkylated Derivatives Dron, Paul I.; Ramešová, Šárka; Holloran, Nicholas P. Electroanalysis, Vol. 28, Issue 11 https://doi.org/10.1002/elan.201600356	journal	February 2016
EPR Spectroscopy of Radical Ions of a 2,3-Diamino-1,4-naphthoquinone Derivative Tarábek, Ján; Wen, Jin; Dron, Paul I. The Journal of Organic Chemistry, Vol. 83, Issue 10 https://doi.org/10.1021/acs.joc.8b00398	journal	April 2018
Magnetic optical activity of d .fwdarw. d transitions. Octahedral chromium (III), cobalt (III), cobalt (II), nickel (II), and manganese (II) complexes McCaffery, Anthony J.; Stephens, Philip J.; Schatz, Paul N. Inorganic Chemistry, Vol. 6, Issue 9 https://doi.org/10.1021/ic50055a002	journal	September 1967
Quantum Mechanics of Many-Electron Systems Dirac, P. A. M. Proceedings of the Royal Society A: Mathematical, Physical and Engineering Sciences, Vol. 123, Issue 792 https://doi.org/10.1098/rspa.1929.0094	journal	April 1929
Accurate spin-dependent electron liquid correlation energies for local spin density calculations: a critical analysis Vosko, S. H.; Wilk, L.; Nusair, M. Canadian Journal of Physics, Vol. 58, Issue 8 https://doi.org/10.1139/p80-159	journal	August 1980
Density-functional exchange-energy approximation with correct asymptotic behavior Becke, A. D. Physical Review A, Vol. 38, Issue 6 https://doi.org/10.1103/physreva.38.3098	journal	September 1988
Optimized accurate auxiliary basis sets for RI-MP2 and RI-CC2 calculations for the atoms Rb to Rn Hellweg, Arnim; Hättig, Christof; Höfener, Sebastian Theoretical Chemistry Accounts, Vol. 117, Issue 4 https://doi.org/10.1007/s00214-007-0250-5	journal	January 2007
Electron affinities of the first‐row atoms revisited. Systematic basis sets and wave functions Kendall, Rick A.; Dunning, Thom H.; Harrison, Robert J. The Journal of Chemical Physics, Vol. 96, Issue 9 https://doi.org/10.1063/1.462569	journal	May 1992
Molcas 8: New capabilities for multiconfigurational quantum chemical calculations across the periodic table : Molcas 8 Aquilante, Francesco; Autschbach, Jochen; Carlson, Rebecca K. Journal of Computational Chemistry, Vol. 37, Issue 5 https://doi.org/10.1002/jcc.24221	journal	November 2015
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
Polarizable dielectric model of solvation with inclusion of charge penetration effects Cossi, Maurizio; Rega, Nadia; Scalmani, Giovanni The Journal of Chemical Physics, Vol. 114, Issue 13 https://doi.org/10.1063/1.1354187	journal	April 2001
Efficient Semi-numerical Implementation of Global and Local Hybrid Functionals for Time-Dependent Density Functional Theory Maier, Toni M.; Bahmann, Hilke; Kaupp, Martin Journal of Chemical Theory and Computation, Vol. 11, Issue 9 https://doi.org/10.1021/acs.jctc.5b00624	journal	August 2015
Efficient Self-Consistent Implementation of Local Hybrid Functionals Bahmann, Hilke; Kaupp, Martin Journal of Chemical Theory and Computation, Vol. 11, Issue 4 https://doi.org/10.1021/ct501137x	journal	March 2015
Efficient molecular numerical integration schemes Treutler, Oliver; Ahlrichs, Reinhart The Journal of Chemical Physics, Vol. 102, Issue 1 https://doi.org/10.1063/1.469408	journal	January 1995
Property-optimized Gaussian basis sets for molecular response calculations Rappoport, Dmitrij; Furche, Filipp The Journal of Chemical Physics, Vol. 133, Issue 13 https://doi.org/10.1063/1.3484283	journal	October 2010
A Reliable Quantum-Chemical Protocol for the Characterization of Organic Mixed-Valence Compounds Renz, Manuel; Theilacker, Kolja; Lambert, Christoph Journal of the American Chemical Society, Vol. 131, Issue 44 https://doi.org/10.1021/ja9070859	journal	November 2009
Development of a TDDFT-Based Protocol with Local Hybrid Functionals for the Screening of Potential Singlet Fission Chromophores Grotjahn, Robin; Maier, Toni M.; Michl, Josef Journal of Chemical Theory and Computation, Vol. 13, Issue 10 https://doi.org/10.1021/acs.jctc.7b00699	journal	September 2017
Time-Dependent Density Functional Response Theory for Molecules Casida, Mark E. Recent Advances in Density Functional Methods https://doi.org/10.1142/9789812830586_0005	book	November 1995
Importance of the correlation contribution for local hybrid functionals: Range separation and self-interaction corrections Arbuznikov, Alexei V.; Kaupp, Martin The Journal of Chemical Physics, Vol. 136, Issue 1 https://doi.org/10.1063/1.3672080	journal	January 2012
Local hybrid functionals: An assessment for thermochemical kinetics Kaupp, Martin; Bahmann, Hilke; Arbuznikov, Alexei V. The Journal of Chemical Physics, Vol. 127, Issue 19 https://doi.org/10.1063/1.2795700	journal	November 2007
Validation of local hybrid functionals for TDDFT calculations of electronic excitation energies Maier, Toni M.; Bahmann, Hilke; Arbuznikov, Alexei V. The Journal of Chemical Physics, Vol. 144, Issue 7 https://doi.org/10.1063/1.4941919	journal	February 2016
A thermochemically competitive local hybrid functional without gradient corrections Bahmann, Hilke; Rodenberg, Alexander; Arbuznikov, Alexei V. The Journal of Chemical Physics, Vol. 126, Issue 1 https://doi.org/10.1063/1.2429058	journal	January 2007
Chemistry with ADF te Velde, G.; Bickelhaupt, F. M.; Baerends, E. J. Journal of Computational Chemistry, Vol. 22, Issue 9, p. 931-967 https://doi.org/10.1002/jcc.1056	journal	January 2001
Towards an order- Fonseca Guerra, C.; Snijders, J. G.; te Velde, G. Theoretical Chemistry Accounts, Vol. 99, Issue 6 https://doi.org/10.1007/s002140050021	journal	January 1998
First-principles calculations of magnetic circular dichroism spectra Ganyushin, Dmitry; Neese, Frank The Journal of Chemical Physics, Vol. 128, Issue 11 https://doi.org/10.1063/1.2894297	journal	March 2008
Magnetic circular dichroism of an unaromatic planar [8]annulene Wen, Jin; Uto, Takayuki; Chalupský, Jakub Journal of Physical Organic Chemistry, Vol. 31, Issue 8 https://doi.org/10.1002/poc.3854	journal	May 2018
An Experimental Test of C−N Bond Twisting in the TICT State: Syn−Anti Photoisomerization in 2-( N -Methyl- N -isopropylamino)-5-cyanopyridine Dobkowski, Jacek; Wójcik, Jacek; Koźmiński, Witold Journal of the American Chemical Society, Vol. 124, Issue 11 https://doi.org/10.1021/ja012326t	journal	March 2002
Prediction of structural and environmental effects on the S1S0 energy gap and jump probability in double-bond cis—trans photoisomeriz Bonačić-Koutecký, Vlasta; Köhler, Jutta; Michl, Josef Chemical Physics Letters, Vol. 104, Issue 5 https://doi.org/10.1016/0009-2614(84)85619-5	journal	February 1984

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Title: Electronic States of 2,3-Diamino-1,4-naphthoquinone and Its N-Alkylated Derivatives

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