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Bis(carbazolyl) derivatives of pyrene and tetrahydropyrene: Synthesis, structures, optical properties, electrochemistry, and electroluminescence

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dc.contributor.author Kaafarani B.R.
dc.contributor.author El-Ballouli A.O.
dc.contributor.author Trattnig R.
dc.contributor.author Fonari A.
dc.contributor.author Sax S.
dc.contributor.author Wex B.
dc.contributor.author Risko C.
dc.contributor.author Khnayzer R.S.
dc.contributor.author Barlow S.
dc.contributor.author Patra D.
dc.contributor.author Timofeeva T.V.
dc.contributor.author List E.J.W.
dc.contributor.author Bredas J.-L.
dc.contributor.author Marder S.R.
dc.contributor.editor
dc.date 2013
dc.date.accessioned 2017-10-03T15:45:32Z
dc.date.available 2017-10-03T15:45:32Z
dc.date.issued 2013
dc.identifier 10.1039/c2tc00474g
dc.identifier.isbn
dc.identifier.issn 20507534
dc.identifier.uri http://hdl.handle.net/10938/12702
dc.description.abstract Tetrahydropyrene and pyrene have been functionalized in their 2,7-positions with carbazole and 3,6-di-tert-butylcarbazole groups, and the properties of these new compounds are compared to analogous carbazole and 3,6-di-tert- butylcarbazole derivatives of benzene and biphenyl using X-ray crystallography, UV-vis absorption and fluorescence spectroscopy, electrochemistry, and quantum-chemical calculations. The absorption spectra are similar to those of their biphenyl-bridged analogues, although TD-DFT calculations indicate a different description of the excited states in the pyrene case, with the lowest observed absorption no longer corresponding to the S0 → S 1 transition. The 3,6-di-tert-butylcarbazole compounds show reversible electrochemical oxidations; the benzene, biphenyl, tetrahydropyrene, or pyrene bridging groups have little impact on the first oxidation potential. Bilayer organic light-emitting diodes incorporating the tetrahydropyrene and pyrene derivatives as emitters show deep-blue electroluminescence. This journal is © The Royal Society of Chemistry 2013.
dc.format.extent
dc.format.extent Pages: (1638-1650)
dc.language English
dc.publisher CAMBRIDGE
dc.relation.ispartof Publication Name: Journal of Materials Chemistry C; Publication Year: 2013; Volume: 1; no. 8; Pages: (1638-1650);
dc.relation.ispartofseries
dc.relation.uri
dc.source Scopus
dc.subject.other
dc.title Bis(carbazolyl) derivatives of pyrene and tetrahydropyrene: Synthesis, structures, optical properties, electrochemistry, and electroluminescence
dc.type Article
dc.contributor.affiliation Kaafarani, B.R., Department of Chemistry, American University of Beirut, Beirut 1107-2020, Lebanon
dc.contributor.affiliation El-Ballouli, A.O., Department of Chemistry, American University of Beirut, Beirut 1107-2020, Lebanon
dc.contributor.affiliation Trattnig, R., NanoTecCenter Weiz Forschungsgesellschaft MbH, Franz-Pichler-Straße 32, A-8160 Weiz, Austria
dc.contributor.affiliation Fonari, A., Department of Biology and Chemistry, New Mexico Highlands University, Las Vegas, NM 87701, United States
dc.contributor.affiliation Sax, S., NanoTecCenter Weiz Forschungsgesellschaft MbH, Franz-Pichler-Straße 32, A-8160 Weiz, Austria
dc.contributor.affiliation Wex, B., Department of Natural Sciences, Lebanese American University, Byblos, Lebanon
dc.contributor.affiliation Risko, C., School of Chemistry and Biochemistry, Center for Organic Photonics and Electronics, Georgia Institute of Technology, Atlanta, GA 30332, United States
dc.contributor.affiliation Khnayzer, R.S., Department of Chemistry, American University of Beirut, Beirut 1107-2020, Lebanon
dc.contributor.affiliation Barlow, S., School of Chemistry and Biochemistry, Center for Organic Photonics and Electronics, Georgia Institute of Technology, Atlanta, GA 30332, United States
dc.contributor.affiliation Patra, D., Department of Chemistry, American University of Beirut, Beirut 1107-2020, Lebanon
dc.contributor.affiliation Timofeeva, T.V., Department of Biology and Chemistry, New Mexico Highlands University, Las Vegas, NM 87701, United States
dc.contributor.affiliation List, E.J.W., NanoTecCenter Weiz Forschungsgesellschaft MbH, Franz-Pichler-Straße 32, A-8160 Weiz, Austria, Institut für Festkörperphysik, Technische Universität, Graz Petersgasse 16, A-8010 Graz, Austria
dc.contributor.affiliation Brédas, J.-L., School of Chemistry and Biochemistry, Center for Organic Photonics and Electronics, Georgia Institute of Technology, Atlanta, GA 30332, United States
dc.contributor.affiliation Marder, S.R., School of Chemistry and Biochemistry, Center for Organic Photonics and Electronics, Georgia Institute of Technology, Atlanta, GA 30332, United States
dc.contributor.authorAddress Kaafarani, B.R.; Department of Chemistry, American University of Beirut, Beirut 1107-2020, Lebanon; email: bilal.kaafarani@aub.edu.lb
dc.contributor.authorCorporate University: American University of Beirut; Faculty: Faculty of Arts and Sciences; Department: Chemistry;
dc.contributor.authorDepartment Chemistry
dc.contributor.authorDivision
dc.contributor.authorEmail bilal.kaafarani@aub.edu.lb
dc.contributor.faculty Faculty of Arts and Sciences
dc.contributor.authorInitials Kaafarani, BR
dc.contributor.authorInitials El-Ballouli, AO
dc.contributor.authorInitials Trattnig, R
dc.contributor.authorInitials Fonari, A
dc.contributor.authorInitials Sax, S
dc.contributor.authorInitials Wex, B
dc.contributor.authorInitials Risko, C
dc.contributor.authorInitials Khnayzer, RS
dc.contributor.authorInitials Barlow, S
dc.contributor.authorInitials Patra, D
dc.contributor.authorInitials Timofeeva, TV
dc.contributor.authorInitials List, EJW
dc.contributor.authorInitials Bredas, JL
dc.contributor.authorInitials Marder, SR
dc.contributor.authorOrcidID
dc.contributor.authorReprintAddress Kaafarani, BR (reprint author), Amer Univ Beirut, Dept Chem, Beirut 11072020, Lebanon.
dc.contributor.authorResearcherID Risko, Chad-A-9785-2014; Bredas, Jean-Luc-A-3431-2008
dc.contributor.authorUniversity American University of Beirut
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dc.description.citedCount 11
dc.description.citedTotWOSCount 15
dc.description.citedWOSCount 15
dc.format.extentCount 13
dc.identifier.articleNo
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dc.identifier.pubmedID
dc.identifier.scopusID 84876927079
dc.identifier.url
dc.publisher.address THOMAS GRAHAM HOUSE, SCIENCE PARK, MILTON RD, CAMBRIDGE CB4 0WF, CAMBS, ENGLAND
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dc.relation.ispartofConferenceDate
dc.relation.ispartofConferenceHosting
dc.relation.ispartofConferenceLoc
dc.relation.ispartofConferenceSponsor
dc.relation.ispartofConferenceTitle
dc.relation.ispartofFundingAgency
dc.relation.ispartOfISOAbbr J. Mater. Chem. C
dc.relation.ispartOfIssue 8
dc.relation.ispartOfPart
dc.relation.ispartofPubTitle Journal of Materials Chemistry C
dc.relation.ispartofPubTitleAbbr J. Mater. Chem. C
dc.relation.ispartOfSpecialIssue
dc.relation.ispartOfSuppl
dc.relation.ispartOfVolume 1
dc.source.ID WOS:000314807800015
dc.type.publication Journal
dc.subject.otherAuthKeyword
dc.subject.otherChemCAS
dc.subject.otherIndex Bilayer organic light-emitting diodes
dc.subject.otherIndex Bridging groups
dc.subject.otherIndex Functionalized
dc.subject.otherIndex Oxidation potentials
dc.subject.otherIndex Pyrene derivatives
dc.subject.otherIndex Quantum-chemical calculation
dc.subject.otherIndex Td-dft calculations
dc.subject.otherIndex UV-vis absorptions
dc.subject.otherIndex Benzene
dc.subject.otherIndex Chemical compounds
dc.subject.otherIndex Density functional theory
dc.subject.otherIndex Electrochemical oxidation
dc.subject.otherIndex Electrochemistry
dc.subject.otherIndex Electroluminescence
dc.subject.otherIndex Fluorescence spectroscopy
dc.subject.otherIndex Light emitting diodes
dc.subject.otherIndex Optical properties
dc.subject.otherIndex Quantum chemistry
dc.subject.otherIndex X ray crystallography
dc.subject.otherIndex Pyrene
dc.subject.otherKeywordPlus LIGHT-EMITTING-DIODES
dc.subject.otherKeywordPlus DENSITY-FUNCTIONAL THEORY
dc.subject.otherKeywordPlus POLYCYCLIC AROMATIC-HYDROCARBONS
dc.subject.otherKeywordPlus HOLE-TRANSPORTING MATERIALS
dc.subject.otherKeywordPlus MIXED-VALENCE SYSTEMS
dc.subject.otherKeywordPlus PHOTOPHYSICAL PROPERTIES
dc.subject.otherKeywordPlus EXCITED-STATES
dc.subject.otherKeywordPlus PHOSPHORESCENT OLEDS
dc.subject.otherKeywordPlus AB-INITIO
dc.subject.otherKeywordPlus SPECTROSCOPIC PROPERTIES
dc.subject.otherWOS Materials Science, Multidisciplinary
dc.subject.otherWOS Physics, Applied


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