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

Research output: Contribution to journalArticle

2 Citations (Scopus)

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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Hydrocarbons
Oligomerization
Hydrogen
Energy gap
Electrons
phenanthrene

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

Majewski, M. A., Chmielewski, P. J., Chien, A., Hong, Y., Lis, T., Witwicki, 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
Majewski, Marcin A. ; Chmielewski, Piotr J. ; Chien, Alan ; Hong, Yongseok ; Lis, Tadeusz ; Witwicki, Maciej ; Kim, Dongho ; Zimmerman, Paul M. ; Stępień, Marcin. / 5,10-Dimesityldiindeno[1,2-a:2′,1′-i]phenanthrene : a stable biradicaloid derived from Chichibabin's hydrocarbon. In: Chemical Science. 2019 ; Vol. 10, No. 11. pp. 3413-3420.
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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.",
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Majewski, MA, Chmielewski, PJ, Chien, A, Hong, Y, Lis, T, Witwicki, M, Kim, D, Zimmerman, PM & Stępień, M 2019, '5,10-Dimesityldiindeno[1,2-a:2′,1′-i]phenanthrene: a stable biradicaloid derived from Chichibabin's hydrocarbon', Chemical Science, vol. 10, no. 11, pp. 3413-3420. https://doi.org/10.1039/c9sc00170k

5,10-Dimesityldiindeno[1,2-a:2′,1′-i]phenanthrene : a stable biradicaloid derived from Chichibabin's hydrocarbon. / Majewski, Marcin A.; Chmielewski, Piotr J.; Chien, Alan; Hong, Yongseok; Lis, Tadeusz; Witwicki, Maciej; Kim, Dongho; Zimmerman, Paul M.; Stępień, Marcin.

In: Chemical Science, Vol. 10, No. 11, 01.01.2019, p. 3413-3420.

Research output: Contribution to journalArticle

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AU - Majewski, Marcin A.

AU - Chmielewski, Piotr J.

AU - Chien, Alan

AU - Hong, Yongseok

AU - Lis, Tadeusz

AU - Witwicki, Maciej

AU - Kim, Dongho

AU - Zimmerman, Paul M.

AU - Stępień, Marcin

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