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

Justin Johnson, Jin Wen, Michal Turowski, Paul Dron, Jakub Chalupsky, Robin Grotjahn, Toni Maier, Steven Fatur, Zdenek Havlas, Martin Kaupp, Josef Michl

Research output: Contribution to journalArticlepeer-review

12 Scopus Citations


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.

Original languageAmerican English
Pages (from-to)60-69
Number of pages10
JournalJournal of Physical Chemistry C
Issue number1
StatePublished - 2020

Bibliographical note

Publisher Copyright:
Copyright © 2019 American Chemical Society.

NREL Publication Number

  • NREL/JA-5900-74492


  • biradicaloid
  • diaminoquinones
  • solar-photochemistry


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