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

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 d...

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Bibliographic Details
Published in:Chemical science (Cambridge) 2019-03, Vol.1 (11), p.3413-342
Main Authors: Majewski, Marcin A, Chmielewski, Piotr J, Chien, Alan, Hong, Yongseok, Lis, Tadeusz, Witwicki, Maciej, Kim, Dongho, Zimmerman, Paul M, St pie, Marcin
Format: Article
Language:English
Subjects:
Atomic energy levels
Crystallography
Hydrocarbons
Oligomerization
Phenanthrene
Stability
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Summary: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 (Δ E S-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. A diindenophenanthrene biradicaloid, formally derived from Chichibabin's hydrocarbon, is obtained in a short, scalable synthesis.
ISSN:2041-6520
2041-6539
DOI:10.1039/c9sc00170k