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

Handle URI:
http://hdl.handle.net/10754/563695
Title:
Highly twisted 1,2:8,9-dibenzozethrenes: Synthesis, ground state, and physical properties
Authors:
Sun, Zhe; Zheng, Bin; Hu, Pan; Huang, Kuo-Wei ( 0000-0003-1900-2658 ) ; Wu, Jishan
Abstract:
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.
KAUST Department:
KAUST Catalysis Center (KCC); Physical Sciences and Engineering (PSE) Division; Chemical Science Program; HCL
Publisher:
Wiley-Blackwell
Journal:
ChemPlusChem
Issue Date:
8-Aug-2014
DOI:
10.1002/cplu.201402127
Type:
Article
ISSN:
21926506
Sponsors:
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.
Is Supplemented By:
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:10.5517/cc11xjl2; HANDLE:http://hdl.handle.net/10754/624302
Appears in Collections:
Articles; Physical Sciences and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)

Full metadata record

DC FieldValue Language
dc.contributor.authorSun, Zheen
dc.contributor.authorZheng, Binen
dc.contributor.authorHu, Panen
dc.contributor.authorHuang, Kuo-Weien
dc.contributor.authorWu, Jishanen
dc.date.accessioned2015-08-03T12:06:43Zen
dc.date.available2015-08-03T12:06:43Zen
dc.date.issued2014-08-08en
dc.identifier.issn21926506en
dc.identifier.doi10.1002/cplu.201402127en
dc.identifier.urihttp://hdl.handle.net/10754/563695en
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.en
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.en
dc.publisherWiley-Blackwellen
dc.subjectAmphoteric redox behavioren
dc.subjectBiradicalen
dc.subjectCyclodimerizationen
dc.subjectDensity functional calculationsen
dc.subjectPolycyclesen
dc.titleHighly twisted 1,2:8,9-dibenzozethrenes: Synthesis, ground state, and physical propertiesen
dc.typeArticleen
dc.contributor.departmentKAUST Catalysis Center (KCC)en
dc.contributor.departmentPhysical Sciences and Engineering (PSE) Divisionen
dc.contributor.departmentChemical Science Programen
dc.contributor.departmentHCLen
dc.identifier.journalChemPlusChemen
dc.contributor.institutionDepartment of Chemistry, National University of Singapore, 3 Science Drive 3Singapore, Singaporeen
kaust.authorZheng, Binen
kaust.authorHuang, Kuo-Weien
dc.relation.isSupplementedBySun, 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/cc11xjl2en
dc.relation.isSupplementedByDOI:10.5517/cc11xjl2en
dc.relation.isSupplementedByHANDLE:http://hdl.handle.net/10754/624302en
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