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

doi:10.1021/acs.jpcc.9b08955

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

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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:

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)

Publication Date:: 2019-11-13

Research Org.:: National Renewable Energy Lab. (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

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.

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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.  https://www.osti.gov/servlets/purl/1595567.

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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 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         = {2019},

  month        = {11}

}

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DOI: 10.1021/acs.jpcc.9b08955

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