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dc.contributor.authorLi, Jinling
dc.contributor.authorJiao, Chongjun
dc.contributor.authorHuang, Kuo-Wei
dc.contributor.authorWu, Jishan
dc.date.accessioned2015-08-03T09:34:08Z
dc.date.available2015-08-03T09:34:08Z
dc.date.issued2011-11-14
dc.identifier.issn09476539
dc.identifier.pmid22083876
dc.identifier.doi10.1002/chem.201102120
dc.identifier.urihttp://hdl.handle.net/10754/561920
dc.description.abstractDiels-Alder cycloaddition reactions at the bay regions of bisanthene (1) with dienophiles such as 1,4-naphthoquinone have been investigated. The products were submitted to nucleophilic addition followed by reductive aromatization reactions to afford the laterally extended bisanthene derivatives 2 and 3. Attempted synthesis of a larger expanded bisanthene 4 revealed an unexpected hydrogenation reaction at the last reductive aromatization step. Unusual Michael addition was observed on quinone 14, which was obtained by Diels-Alder reaction between 1 and 1,4-anthraquinone. Compounds 1-3 exhibited near-infrared (NIR) absorption and emission with high-to-moderate fluorescent quantum yields. Their structures and absorption spectra were studied by density function theory and non-planar twisted structures were calculated for 2 and 3. All compounds showed amphoteric redox behavior with multiple oxidation/reduction waves. Oxidative titration with SbCl 5 gave stable radical cations, and the process was followed by UV/Vis/NIR spectroscopic measurements. Their photostability was measured and correlated to their different geometries and electronic structures. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
dc.description.sponsorshipJ. W. acknowledges financial support from Singapore DSTA DIRP Project (DSTA-NUS-DIRP/2008/03), the NRF Competitive Research Program (R-143-000-360-281), and A*Star BMRC grant (No. 10/1/21/19/642). K.-W. H. acknowledges financial support from KAUST.
dc.publisherWiley
dc.subjectcycloaddition
dc.subjectdyes/pigments
dc.subjecthyperconjugation
dc.subjectMichael addition
dc.subjectpolycycles
dc.titleLateral extension of π conjugation along the bay regions of bisanthene through a diels-alder cycloaddition reaction
dc.typeArticle
dc.contributor.departmentBiological and Environmental Sciences and Engineering (BESE) Division
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.journalChemistry - A European Journal
dc.contributor.institutionDepartment of Chemistry, National University of Singapore, 3 Science Drive 3, 117543 Singapore, Singapore
kaust.personHuang, Kuo-Wei
dc.date.published-online2011-11-14
dc.date.published-print2011-12-16


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