Highly twisted 1,2:8,9-dibenzozethrenes: Synthesis, ground state, and physical properties

Zhe Sun, Bin Zheng, Pan Hu, Kuo-Wei Huang, Jishan Wu

Research output: Contribution to journalArticlepeer-review

17 Scopus citations


Two soluble and stable 1,2:8,9-dibenzozethrene derivatives (3a,b) are synthesized through a palladium-catalyzed cyclodimerization reaction. X-ray crystallographic analysis shows that these molecules are highly twisted owing to congestion at the cove region. Broken-symmetry DFT calculations predict that they have a singlet biradical ground state with a smaller biradical character and a large singlet-triplet energy gap; these predictions are supported by NMR and electronic absorption measurements. They have small energy gaps and exhibit farred/near-infrared absorption/emission and amphoteric redox behaviors.
Original languageEnglish (US)
Pages (from-to)1549-1553
Number of pages5
Issue number11
StatePublished - Aug 8 2014

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: J.W. acknowledges financial support from the BMRC grant (10/1/21/19/642), MOE Tier 2 grant (MOE2011-T2-2-130), and MINDEF-NUS JPP (Grant 12-02-05). K.W.H. acknowledges support from MUST. We thank Dr. Tan Geok Kheng for the crystallographic analysis of 3b.

ASJC Scopus subject areas

  • General Chemistry


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