EPR Spectroscopy of Radical Ions of a 2,3-Diamino-1,4-naphthoquinone Derivative
JOURNAL OF ORGANIC CHEMISTRY, cilt.83, sa.10, ss.5474-5479, 2018 (SCI-Expanded, Scopus)
- Yayın Türü: Makale / Tam Makale
- Cilt numarası: 83 Sayı: 10
- Basım Tarihi: 2018
- Doi Numarası: 10.1021/acs.joc.8b00398
- Dergi Adı: JOURNAL OF ORGANIC CHEMISTRY
- Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Index Chemicus (IC)
- Sayfa Sayıları: ss.5474-5479
- Orta Doğu Teknik Üniversitesi Adresli: Hayır
Özet
We report the electron paramagnetic resonance spectra of the radical cation and radical anion of 1,2,2,3-tetramethy1-2,3-dihydro-1H-naphtho-[2,3-d]-imidazole-4,9-dione (1) and its doubly C-13 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(.-).