Search Menu
DOE PAGES title logo U.S. Department of Energy
Office of Scientific and Technical Information
Search Scholarly Publications

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

Abstract

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.

Authors:
 [1];  [2];  [2];  [1]; ORCiD logo [3]; ORCiD logo [3]; ORCiD logo [2];  [1]; ORCiD logo [4]; ORCiD logo [3]; ORCiD logo [5]
+ Show Author Affiliations
  1. Inst. of Organic Chemistry and Biochemistry, Prague (Czech Republic)
  2. Univ. of Colorado, Boulder, CO (United States)
  3. Technische Univ. Berlin (Germany)
  4. National Renewable Energy Lab. (NREL), Golden, CO (United States)
  5. Inst. of Organic Chemistry and Biochemistry, Prague (Czech Republic); Univ. of Colorado, Boulder, CO (United States)
Publication Date:
Research Org.:
National Renewable Energy Laboratory (NREL), Golden, CO (United States); Univ. of Colorado, Boulder, CO (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES)
OSTI Identifier:
1595567
Alternate Identifier(s):
OSTI ID: 1688409
Report Number(s):
NREL/JA-5900-74492
Journal ID: ISSN 1932-7447; TRN: US2100663
Grant/Contract Number:  
AC36-08GO28308; SC0007004
Resource Type:
Accepted Manuscript
Journal Name:
Journal of Physical Chemistry. C
Additional Journal Information:
Journal Volume: 124; Journal Issue: 1; Journal ID: ISSN 1932-7447
Publisher:
American Chemical Society
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; diaminoquinones; biradicaloid

Citation Formats

Wen, Jin, Turowski, Michał, Dron, Paul I., Chalupský, Jakub, Grotjahn, Robin, Maier, Toni M., Fatur, Steven M., Havlas, Zdeněk, Johnson, Justin C., Kaupp, Martin, and Michl, Josef. Electronic States of 2,3-Diamino-1,4-naphthoquinone and Its N-Alkylated Derivatives. United States: N. p., 2019. Web. doi:10.1021/acs.jpcc.9b08955.
Copy to clipboard
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. Electronic States of 2,3-Diamino-1,4-naphthoquinone and Its N-Alkylated Derivatives. United States. https://doi.org/10.1021/acs.jpcc.9b08955
Copy to clipboard
Wen, Jin, Turowski, Michał, Dron, Paul I., Chalupský, Jakub, Grotjahn, Robin, Maier, Toni M., Fatur, Steven M., Havlas, Zdeněk, Johnson, Justin C., Kaupp, Martin, and Michl, Josef. Wed . "Electronic States of 2,3-Diamino-1,4-naphthoquinone and Its N-Alkylated Derivatives". United States. https://doi.org/10.1021/acs.jpcc.9b08955. https://www.osti.gov/servlets/purl/1595567.
Copy to clipboard
@article{osti_1595567,
title = {Electronic States of 2,3-Diamino-1,4-naphthoquinone and Its N-Alkylated Derivatives},
author = {Wen, Jin and Turowski, Michał and Dron, Paul I. and Chalupský, Jakub and Grotjahn, Robin and Maier, Toni M. and Fatur, Steven M. and Havlas, Zdeněk and Johnson, Justin C. and Kaupp, Martin and Michl, Josef},
abstractNote = {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.},
doi = {10.1021/acs.jpcc.9b08955},
journal = {Journal of Physical Chemistry. C},
number = 1,
volume = 124,
place = {United States},
year = {Wed Nov 13 00:00:00 EST 2019},
month = {Wed Nov 13 00:00:00 EST 2019}
}
Copy to clipboard
Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record
https://doi.org/10.1021/acs.jpcc.9b08955
Copyright Statement
Other availability
Search WorldCat Search WorldCat to find libraries that may hold this journal
Citation Metrics:
Cited by: 11 works
Citation information provided by
Web of Science
Save / Share:
Export Metadata
Save to My Library
You must Sign In or Create an Account in order to save documents to your library.

Works referenced in this record:

Singlet Fission
journal, November 2010

  • Smith, Millicent B.; Michl, Josef
  • Chemical Reviews, Vol. 110, Issue 11
  • DOI: 10.1021/cr1002613

Recent Advances in Singlet Fission
journal, April 2013

Detailed Balance Limit of Efficiency of p‐n Junction Solar Cells
journal, March 1961

  • Shockley, William; Queisser, Hans J.
  • Journal of Applied Physics, Vol. 32, Issue 3, p. 510-519
  • DOI: 10.1063/1.1736034

Solar conversion efficiency of photovoltaic and photoelectrolysis cells with carrier multiplication absorbers
journal, October 2006

  • Hanna, M. C.; Nozik, A. J.
  • Journal of Applied Physics, Vol. 100, Issue 7
  • DOI: 10.1063/1.2356795

Singlet Fission for Dye-Sensitized Solar Cells:  Can a Suitable Sensitizer Be Found?
journal, December 2006

  • Paci, Irina; Johnson, Justin C.; Chen, Xudong
  • Journal of the American Chemical Society, Vol. 128, Issue 51
  • DOI: 10.1021/ja063980h

Guidance for Mutual Disposition of Chromophores for Singlet Fission
journal, October 2015

Singlet Fission: Optimization of Chromophore Dimer Geometry
book, May 2017

Captodatively Stabilized Biradicaloids as Chromophores for Singlet Fission
journal, December 2014

  • Wen, Jin; Havlas, Zdenĕk; Michl, Josef
  • Journal of the American Chemical Society, Vol. 137, Issue 1
  • DOI: 10.1021/ja5070476

Structural Changes Accompanying Intramolecular Electron Transfer:  Focus on Twisted Intramolecular Charge-Transfer States and Structures
journal, October 2003

  • Grabowski, Zbigniew R.; Rotkiewicz, Krystyna; Rettig, Wolfgang
  • Chemical Reviews, Vol. 103, Issue 10
  • DOI: 10.1021/cr940745l

Redox Behavior of 2,3-Diamino-1,4-naphthoquinone and its N -Alkylated Derivatives
journal, February 2016

  • Dron, Paul I.; Ramešová, Šárka; Holloran, Nicholas P.
  • Electroanalysis, Vol. 28, Issue 11
  • DOI: 10.1002/elan.201600356

EPR Spectroscopy of Radical Ions of a 2,3-Diamino-1,4-naphthoquinone Derivative
journal, April 2018

  • Tarábek, Ján; Wen, Jin; Dron, Paul I.
  • The Journal of Organic Chemistry, Vol. 83, Issue 10
  • DOI: 10.1021/acs.joc.8b00398

Magnetic optical activity of d .fwdarw. d transitions. Octahedral chromium (III), cobalt (III), cobalt (II), nickel (II), and manganese (II) complexes
journal, September 1967

  • McCaffery, Anthony J.; Stephens, Philip J.; Schatz, Paul N.
  • Inorganic Chemistry, Vol. 6, Issue 9
  • DOI: 10.1021/ic50055a002

Quantum Mechanics of Many-Electron Systems
journal, April 1929

  • Dirac, P. A. M.
  • Proceedings of the Royal Society A: Mathematical, Physical and Engineering Sciences, Vol. 123, Issue 792
  • DOI: 10.1098/rspa.1929.0094

Accurate spin-dependent electron liquid correlation energies for local spin density calculations: a critical analysis
journal, August 1980

  • Vosko, S. H.; Wilk, L.; Nusair, M.
  • Canadian Journal of Physics, Vol. 58, Issue 8
  • DOI: 10.1139/p80-159

Density-functional exchange-energy approximation with correct asymptotic behavior
journal, September 1988

Optimized accurate auxiliary basis sets for RI-MP2 and RI-CC2 calculations for the atoms Rb to Rn
journal, January 2007

  • Hellweg, Arnim; Hättig, Christof; Höfener, Sebastian
  • Theoretical Chemistry Accounts, Vol. 117, Issue 4
  • DOI: 10.1007/s00214-007-0250-5

Electron affinities of the first‐row atoms revisited. Systematic basis sets and wave functions
journal, May 1992

  • Kendall, Rick A.; Dunning, Thom H.; Harrison, Robert J.
  • The Journal of Chemical Physics, Vol. 96, Issue 9
  • DOI: 10.1063/1.462569

Molcas 8: New capabilities for multiconfigurational quantum chemical calculations across the periodic table : Molcas 8
journal, November 2015

  • Aquilante, Francesco; Autschbach, Jochen; Carlson, Rebecca K.
  • Journal of Computational Chemistry, Vol. 37, Issue 5
  • DOI: 10.1002/jcc.24221

Quantum Calculation of Molecular Energies and Energy Gradients in Solution by a Conductor Solvent Model
journal, March 1998

  • Barone, Vincenzo; Cossi, Maurizio
  • The Journal of Physical Chemistry A, Vol. 102, Issue 11
  • DOI: 10.1021/jp9716997

Polarizable dielectric model of solvation with inclusion of charge penetration effects
journal, April 2001

  • Cossi, Maurizio; Rega, Nadia; Scalmani, Giovanni
  • The Journal of Chemical Physics, Vol. 114, Issue 13
  • DOI: 10.1063/1.1354187

Efficient Semi-numerical Implementation of Global and Local Hybrid Functionals for Time-Dependent Density Functional Theory
journal, August 2015

  • Maier, Toni M.; Bahmann, Hilke; Kaupp, Martin
  • Journal of Chemical Theory and Computation, Vol. 11, Issue 9
  • DOI: 10.1021/acs.jctc.5b00624

Efficient Self-Consistent Implementation of Local Hybrid Functionals
journal, March 2015

  • Bahmann, Hilke; Kaupp, Martin
  • Journal of Chemical Theory and Computation, Vol. 11, Issue 4
  • DOI: 10.1021/ct501137x

Efficient molecular numerical integration schemes
journal, January 1995

  • Treutler, Oliver; Ahlrichs, Reinhart
  • The Journal of Chemical Physics, Vol. 102, Issue 1
  • DOI: 10.1063/1.469408

Property-optimized Gaussian basis sets for molecular response calculations
journal, October 2010

  • Rappoport, Dmitrij; Furche, Filipp
  • The Journal of Chemical Physics, Vol. 133, Issue 13
  • DOI: 10.1063/1.3484283

A Reliable Quantum-Chemical Protocol for the Characterization of Organic Mixed-Valence Compounds
journal, November 2009

  • Renz, Manuel; Theilacker, Kolja; Lambert, Christoph
  • Journal of the American Chemical Society, Vol. 131, Issue 44
  • DOI: 10.1021/ja9070859

Development of a TDDFT-Based Protocol with Local Hybrid Functionals for the Screening of Potential Singlet Fission Chromophores
journal, September 2017

  • Grotjahn, Robin; Maier, Toni M.; Michl, Josef
  • Journal of Chemical Theory and Computation, Vol. 13, Issue 10
  • DOI: 10.1021/acs.jctc.7b00699

Time-Dependent Density Functional Response Theory for Molecules
book, November 1995

Importance of the correlation contribution for local hybrid functionals: Range separation and self-interaction corrections
journal, January 2012

  • Arbuznikov, Alexei V.; Kaupp, Martin
  • The Journal of Chemical Physics, Vol. 136, Issue 1
  • DOI: 10.1063/1.3672080

Local hybrid functionals: An assessment for thermochemical kinetics
journal, November 2007

  • Kaupp, Martin; Bahmann, Hilke; Arbuznikov, Alexei V.
  • The Journal of Chemical Physics, Vol. 127, Issue 19
  • DOI: 10.1063/1.2795700

Validation of local hybrid functionals for TDDFT calculations of electronic excitation energies
journal, February 2016

  • Maier, Toni M.; Bahmann, Hilke; Arbuznikov, Alexei V.
  • The Journal of Chemical Physics, Vol. 144, Issue 7
  • DOI: 10.1063/1.4941919

A thermochemically competitive local hybrid functional without gradient corrections
journal, January 2007

  • Bahmann, Hilke; Rodenberg, Alexander; Arbuznikov, Alexei V.
  • The Journal of Chemical Physics, Vol. 126, Issue 1
  • DOI: 10.1063/1.2429058

Chemistry with ADF
journal, January 2001

  • te Velde, G.; Bickelhaupt, F. M.; Baerends, E. J.
  • Journal of Computational Chemistry, Vol. 22, Issue 9, p. 931-967
  • DOI: 10.1002/jcc.1056

Towards an order-
journal, January 1998

  • Fonseca Guerra, C.; Snijders, J. G.; te Velde, G.
  • Theoretical Chemistry Accounts, Vol. 99, Issue 6
  • DOI: 10.1007/s002140050021

First-principles calculations of magnetic circular dichroism spectra
journal, March 2008

  • Ganyushin, Dmitry; Neese, Frank
  • The Journal of Chemical Physics, Vol. 128, Issue 11
  • DOI: 10.1063/1.2894297

Magnetic circular dichroism of an unaromatic planar [8]annulene
journal, May 2018

  • Wen, Jin; Uto, Takayuki; Chalupský, Jakub
  • Journal of Physical Organic Chemistry, Vol. 31, Issue 8
  • DOI: 10.1002/poc.3854

An Experimental Test of C−N Bond Twisting in the TICT State: Syn−Anti Photoisomerization in 2-( N -Methyl- N -isopropylamino)-5-cyanopyridine
journal, March 2002

  • Dobkowski, Jacek; Wójcik, Jacek; Koźmiński, Witold
  • Journal of the American Chemical Society, Vol. 124, Issue 11
  • DOI: 10.1021/ja012326t

Prediction of structural and environmental effects on the S1S0 energy gap and jump probability in double-bond cis—trans photoisomeriz
journal, February 1984

    Sort by:
    [ × clear filter / sort ]

    Similar Records in DOE PAGES and OSTI.GOV collections:

    Other research related to this record: