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Title: EPR Spectroscopy of Radical Ions of a 2,3-Diamino-1,4-naphthoquinone Derivative

Journal Article · · Journal of Organic Chemistry
ORCiD logo [1];  [2];  [3]; ORCiD logo [4]; ORCiD logo [5]
  1. Inst. of Organic Chemistry and Biochemistry, Prague (Czech Republic); University of Colorado
  2. Inst. of Organic Chemistry and Biochemistry, Prague (Czech Republic)
  3. Univ. of Colorado, Boulder, CO (United States)
  4. Inst. of Organic Chemistry and Biochemistry, Prague (Czech Republic); J. Heyrovský Inst. of Physical Chemistry, Prague (Czech Republic)
  5. Inst. of Organic Chemistry and Biochemistry, Prague (Czech Republic); Univ. of Colorado, Boulder, CO (United States)
+ Show Author Affiliations

We report the electron paramagnetic resonance spectra of the radical cation and radical anion of 1,2,2,3-tetramethyl-2,3-dihydro-1H-naphtho[2,3-d]imidazole-4,9-dione (1) and its doubly 13C labeled analogue 2, of interest for singlet fission. The hyperfine coupling constants are in excellent agreement with density functional theory calculations and establish the structures beyond doubt. Unlike the radical cation 1•+, the radical anion 1•– and its parent 1 have pyramidalized nitrogen atoms and inequivalent methyl groups 15 and 16, in agreement with the calculations. The distinction is particularly clear with the labeled analogue 2•–.

Research Organization:
Univ. of Colorado, Boulder, CO (United States)
Sponsoring Organization:
Academy of Sciences of the Czech Republic; Grant Agency of the Czech Republic; USDOE Office of Science (SC), Basic Energy Sciences (BES)
Grant/Contract Number:
SC0007004
OSTI ID:
1688393
Journal Information:
Journal of Organic Chemistry, Journal Name: Journal of Organic Chemistry Journal Issue: 10 Vol. 83; ISSN 0022-3263
Publisher:
American Chemical SocietyCopyright Statement
Country of Publication:
United States
Language:
English

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Captodatively Stabilized Biradicaloids as Chromophores for Singlet Fission journal December 2014
Quantum Calculation of Molecular Energies and Energy Gradients in Solution by a Conductor Solvent Model journal March 1998
Solar conversion efficiency of photovoltaic and photoelectrolysis cells with carrier multiplication absorbers journal October 2006
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Radical decomposition of N,N-bis-(3-chloro-1,4-naphthoquinon-2-yl) amine in basic conditions followed by EPR journal April 2003

Cited By (2)

Two zinc coordination polymers with photochromic behaviors and photo-controlled luminescence properties journal January 2020
Synthesis of Amino Acid–Naphthoquinones and In Vitro Studies on Cervical and Breast Cell Lines journal November 2019

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