5,10-Dimesityldiindeno[1,2-a:2′,1′-i]phenanthrene: a stable biradicaloid derived from Chichibabin's hydrocarbon

Marcin A. Majewski, Piotr J. Chmielewski, Alan Chien, Yongseok Hong, Tadeusz Lis, Maciej Witwicki, Dongho Kim, Paul M. Zimmerman, Marcin Stępień

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Abstract

A diindenophenanthrene biradicaloid, formally derived from Chichibabin's hydrocarbon, is obtained in a short, scalable synthesis. The present system is electron-rich and devoid of conjugated substituents, and still exhibits very good stability under ambient conditions. The introduction of the diindeno[1,2-a:2′,1′-i] phenanthrene ring framework results in a singlet biradicaloid system with an easily accessible triplet state (ΔES-T = −1.30 kcal mol−1) and a small electronic bandgap (1.39 V). The stability limits of the title hydrocarbon were explored systematically in the solid state, to reveal an unusual thermally initiated hydrogen-scrambling oligomerization process.

Original languageEnglish
Pages (from-to)3413-3420
Number of pages8
JournalChemical Science
Volume10
Issue number11
DOIs
Publication statusPublished - 2019 Jan 1

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All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

Majewski, M. A., Chmielewski, P. J., Chien, A., Hong, Y., Lis, T., Witwicki, M., Kim, D., Zimmerman, P. M., & Stępień, M. (2019). 5,10-Dimesityldiindeno[1,2-a:2′,1′-i]phenanthrene: a stable biradicaloid derived from Chichibabin's hydrocarbon. Chemical Science, 10(11), 3413-3420. https://doi.org/10.1039/c9sc00170k