Issue 11, 2019

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

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.

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

Supplementary files

Article information

Article type
Edge Article
Submitted
11 jan 2019
Accepted
05 feb 2019
First published
07 feb 2019
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2019,10, 3413-3420

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

M. A. Majewski, P. J. Chmielewski, A. Chien, Y. Hong, T. Lis, M. Witwicki, D. Kim, P. M. Zimmerman and M. Stępień, Chem. Sci., 2019, 10, 3413 DOI: 10.1039/C9SC00170K

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