Jump to main content
Jump to site search
Access to RSC content Close the message box

Continue to access RSC content when you are not at your institution. Follow our step-by-step guide.


Issue 11, 2019
Previous Article Next Article

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

Author affiliations

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

Back to tab navigation

Supplementary files

Article information


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

Chem. Sci., 2019,10, 3413-3420
Article type
Edge Article

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

This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. Material from this article can be used in other publications provided that the correct acknowledgement is given with the reproduced material and it is not used for commercial purposes.

Reproduced material should be attributed as follows:

  • For reproduction of material from NJC:
    [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC.
  • For reproduction of material from PCCP:
    [Original citation] - Published by the PCCP Owner Societies.
  • For reproduction of material from PPS:
    [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC.
  • For reproduction of material from all other RSC journals:
    [Original citation] - Published by The Royal Society of Chemistry.

Information about reproducing material from RSC articles with different licences is available on our Permission Requests page.


Social activity

Search articles by author

Spotlight

Advertisements