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

Abstract

Diaminoquinones with a captodatively stabilized biradicaloid structure are options 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 Lab. (NREL), Golden, CO (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)
OSTI Identifier:
1595567
Report Number(s):
NREL/JA-5900-74492
Journal ID: ISSN 1932-7447
Grant/Contract Number:  
AC36-08GO28308
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.
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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. doi:10.1021/acs.jpcc.9b08955.
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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. doi:10.1021/acs.jpcc.9b08955.
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@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 options 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 = {2019},
month = {11}
}
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Journal Article:
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This content will become publicly available on November 13, 2020
Publisher's Version of Record
DOI:  10.1021/acs.jpcc.9b08955
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