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 UTC 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 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.

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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) (SC-22)

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

OSTI ID:: 1595567

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

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

Publisher:: American Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: English

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37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
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diaminoquinones

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

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