Electronic States of 2,3-Diamino-1,4-naphthoquinone and Its N‑Alkylated Derivatives
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 transi...
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| Veröffentlicht in: | Journal of physical chemistry. C 2020-01, Vol.124 (1), p.60-69 |
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| container_title | Journal of physical chemistry. C |
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| creator | 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 |
| description | 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_str_mv | 10.1021/acs.jpcc.9b08955 |
| format | Article |
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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.</description><identifier>ISSN: 1932-7447</identifier><identifier>EISSN: 1932-7455</identifier><identifier>DOI: 10.1021/acs.jpcc.9b08955</identifier><language>eng</language><publisher>WASHINGTON: American Chemical Society</publisher><subject>Chemistry ; Chemistry, Physical ; Materials Science ; Materials Science, Multidisciplinary ; Nanoscience & Nanotechnology ; Physical Sciences ; Science & Technology ; Science & Technology - Other Topics ; Technology</subject><ispartof>Journal of physical chemistry. 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C</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wen, Jin</au><au>Turowski, Michał</au><au>Dron, Paul I</au><au>Chalupský, Jakub</au><au>Grotjahn, Robin</au><au>Maier, Toni M</au><au>Fatur, Steven M</au><au>Havlas, Zdeněk</au><au>Johnson, Justin C</au><au>Kaupp, Martin</au><au>Michl, Josef</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Electronic States of 2,3-Diamino-1,4-naphthoquinone and Its N‑Alkylated Derivatives</atitle><jtitle>Journal of physical chemistry. C</jtitle><stitle>J PHYS CHEM C</stitle><addtitle>J. Phys. Chem. C</addtitle><date>2020-01-09</date><risdate>2020</risdate><volume>124</volume><issue>1</issue><spage>60</spage><epage>69</epage><pages>60-69</pages><issn>1932-7447</issn><eissn>1932-7455</eissn><abstract>Diaminoquinones with a captodatively stabilized biradicaloid structure are candidates for singlet fission, but few such compounds are known. 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| subjects | Chemistry Chemistry, Physical Materials Science Materials Science, Multidisciplinary Nanoscience & Nanotechnology Physical Sciences Science & Technology Science & Technology - Other Topics Technology |
| title | Electronic States of 2,3-Diamino-1,4-naphthoquinone and Its N‑Alkylated Derivatives |
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