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dc.contributor.authorSun, Zhe
dc.contributor.authorZheng, Bin
dc.contributor.authorHu, Pan
dc.contributor.authorHuang, Kuo-Wei
dc.contributor.authorWu, Jishan
dc.date.accessioned2015-08-03T12:06:43Z
dc.date.available2015-08-03T12:06:43Z
dc.date.issued2014-08-08
dc.identifier.citationSun, Z., Zheng, B., Hu, P., Huang, K.-W., & Wu, J. (2014). Highly Twisted 1,2:8,9-Dibenzozethrenes: Synthesis, Ground State, and Physical Properties. ChemPlusChem, 79(11), 1549–1553. doi:10.1002/cplu.201402127
dc.identifier.issn21926506
dc.identifier.doi10.1002/cplu.201402127
dc.identifier.urihttp://hdl.handle.net/10754/563695
dc.description.abstractTwo 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.
dc.description.sponsorshipJ.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.
dc.publisherWiley
dc.subjectAmphoteric redox behavior
dc.subjectBiradical
dc.subjectCyclodimerization
dc.subjectDensity functional calculations
dc.subjectPolycycles
dc.titleHighly twisted 1,2:8,9-dibenzozethrenes: Synthesis, ground state, and physical properties
dc.typeArticle
dc.contributor.departmentChemical Science Program
dc.contributor.departmentHomogeneous Catalysis Laboratory (HCL)
dc.contributor.departmentKAUST Catalysis Center (KCC)
dc.contributor.departmentPhysical Science and Engineering (PSE) Division
dc.identifier.journalChemPlusChem
dc.contributor.institutionDepartment of Chemistry, National University of Singapore, 3 Science Drive 3Singapore, Singapore
kaust.personZheng, Bin
kaust.personHuang, Kuo-Wei
dc.relation.issupplementedbyDOI:10.5517/cc11xjl2
display.relations<b> Is Supplemented By:</b> <br/> <ul><li><i>[Dataset]</i> <br/> Sun, Z., Zheng, B., Hu, P., Huang, K.-W., & Wu, J. (2014). CCDC 980734: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc11xjl2. DOI: <a href="https://doi.org/10.5517/cc11xjl2">10.5517/cc11xjl2</a> HANDLE: <a href="http://hdl.handle.net/10754/624302">10754/624302</a></li></ul>
dc.date.published-online2014-08-08
dc.date.published-print2014-11


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