Tetraaryl pyrenes: photophysical properties, computational studies, crystal structures, and application in OLEDs

Handle URI:
http://hdl.handle.net/10754/621615
Title:
Tetraaryl pyrenes: photophysical properties, computational studies, crystal structures, and application in OLEDs
Authors:
El-Assaad, Tarek H.; Auer, Manuel; Castañeda, Raul; Hallal, Kassem M.; Jradi, Fadi M.; Mosca, Lorenzo; Khnayzer, Rony S.; Patra, Digambara; Timofeeva, Tatiana V.; Bredas, Jean-Luc ( 0000-0001-7278-4471 ) ; List-Kratochvil, Emil J. W.; Wex, Brigitte; Kaafarani, Bilal R.
Abstract:
Pyrene was derivatized in positions 1, 3, 6, and 8 to yield a series of nine tetraarylpyrenes for which absorption, emission, emission lifetimes and solvatochromism in solution were determined. The fluorescence quantum yields in thin films and crystalline state, electrochemistry, and quantum-chemical calculations were completed for the series along with the X-ray crystal structure analysis of compounds 1, 2, 4, 5, 7, and 9. Compounds 2, 3, 4 as well as 7 were identified as the most suitable candidates for OLED application. Notably, in an unoptimized single-layer device geometry, these compounds exhibited blue electroluminescence coupled with impressively low turn-on voltages and high maximum luminances such as 2.8 V and 13 542 cd m-2 at 8.2 V for compound 2, respectively. © The Royal Society of Chemistry 2016.
KAUST Department:
Physical Sciences and Engineering (PSE) Division; Solar and Photovoltaic Engineering Research Center (SPERC)
Citation:
El-Assaad TH, Auer M, Castañeda R, Hallal KM, Jradi FM, et al. (2016) Tetraaryl pyrenes: photophysical properties, computational studies, crystal structures, and application in OLEDs. J Mater Chem C 4: 3041–3058. Available: http://dx.doi.org/10.1039/C5TC02849C.
Publisher:
Royal Society of Chemistry (RSC)
Journal:
J. Mater. Chem. C
Issue Date:
15-Oct-2015
DOI:
10.1039/C5TC02849C
Type:
Article
ISSN:
2050-7526; 2050-7534
Sponsors:
This work was supported by the Petroleum Research Fund (PRF) of the American Chemical Society (grant #: 47343-B10). The authors are grateful to this support. B.R.K. and B.W. acknowledge the Arab Fund Scholarship Program for financial support. The authors thank Dr. Veaceslav Coropceanu, Mr. Alexandr Fonari and Mr. Stephen B. Shirring for fruitful discussions. M.A. gratefully acknowledges the financial support of the Klima- und Energiefonds Project PLASMOLED 3726090. TVT and RC were supported by NSF PREM grants DMR-0934212 and DMR-1523611.
Is Supplemented By:
El-Assaad, T. H., Auer, M., Castañeda, R., Hallal, K. M., Jradi, F. M., Mosca, L., … Kaafarani, B. R. (2015). CCDC 1011328: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc12ychw; DOI:10.5517/cc12ychw; HANDLE:http://hdl.handle.net/10754/624351; El-Assaad, T. H., Auer, M., Castañeda, R., Hallal, K. M., Jradi, F. M., Mosca, L., … Kaafarani, B. R. (2015). CCDC 1011330: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc12ycky; DOI:10.5517/cc12ycky; HANDLE:http://hdl.handle.net/10754/624352; El-Assaad, T. H., Auer, M., Castañeda, R., Hallal, K. M., Jradi, F. M., Mosca, L., … Kaafarani, B. R. (2015). CCDC 1015949: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc1335ky; DOI:10.5517/cc1335ky; HANDLE:http://hdl.handle.net/10754/624354; El-Assaad, T. H., Auer, M., Castañeda, R., Hallal, K. M., Jradi, F. M., Mosca, L., … Kaafarani, B. R. (2015). CCDC 1015953: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc1335p2; DOI:10.5517/cc1335p2; HANDLE:http://hdl.handle.net/10754/624355; El-Assaad, T. H., Auer, M., Castañeda, R., Hallal, K. M., Jradi, F. M., Mosca, L., … Kaafarani, B. R. (2015). CCDC 1039264: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc13wfn2; DOI:10.5517/cc13wfn2; HANDLE:http://hdl.handle.net/10754/624393; El-Assaad, T. H., Auer, M., Castañeda, R., Hallal, K. M., Jradi, F. M., Mosca, L., … Kaafarani, B. R. (2015). CCDC 1044326: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc141pyt; DOI:10.5517/cc141pyt; HANDLE:http://hdl.handle.net/10754/624397
Appears in Collections:
Articles; Physical Sciences and Engineering (PSE) Division; Solar and Photovoltaic Engineering Research Center (SPERC)

Full metadata record

DC FieldValue Language
dc.contributor.authorEl-Assaad, Tarek H.en
dc.contributor.authorAuer, Manuelen
dc.contributor.authorCastañeda, Raulen
dc.contributor.authorHallal, Kassem M.en
dc.contributor.authorJradi, Fadi M.en
dc.contributor.authorMosca, Lorenzoen
dc.contributor.authorKhnayzer, Rony S.en
dc.contributor.authorPatra, Digambaraen
dc.contributor.authorTimofeeva, Tatiana V.en
dc.contributor.authorBredas, Jean-Lucen
dc.contributor.authorList-Kratochvil, Emil J. W.en
dc.contributor.authorWex, Brigitteen
dc.contributor.authorKaafarani, Bilal R.en
dc.date.accessioned2016-11-03T08:33:24Z-
dc.date.available2016-11-03T08:33:24Z-
dc.date.issued2015-10-15en
dc.identifier.citationEl-Assaad TH, Auer M, Castañeda R, Hallal KM, Jradi FM, et al. (2016) Tetraaryl pyrenes: photophysical properties, computational studies, crystal structures, and application in OLEDs. J Mater Chem C 4: 3041–3058. Available: http://dx.doi.org/10.1039/C5TC02849C.en
dc.identifier.issn2050-7526en
dc.identifier.issn2050-7534en
dc.identifier.doi10.1039/C5TC02849Cen
dc.identifier.urihttp://hdl.handle.net/10754/621615-
dc.description.abstractPyrene was derivatized in positions 1, 3, 6, and 8 to yield a series of nine tetraarylpyrenes for which absorption, emission, emission lifetimes and solvatochromism in solution were determined. The fluorescence quantum yields in thin films and crystalline state, electrochemistry, and quantum-chemical calculations were completed for the series along with the X-ray crystal structure analysis of compounds 1, 2, 4, 5, 7, and 9. Compounds 2, 3, 4 as well as 7 were identified as the most suitable candidates for OLED application. Notably, in an unoptimized single-layer device geometry, these compounds exhibited blue electroluminescence coupled with impressively low turn-on voltages and high maximum luminances such as 2.8 V and 13 542 cd m-2 at 8.2 V for compound 2, respectively. © The Royal Society of Chemistry 2016.en
dc.description.sponsorshipThis work was supported by the Petroleum Research Fund (PRF) of the American Chemical Society (grant #: 47343-B10). The authors are grateful to this support. B.R.K. and B.W. acknowledge the Arab Fund Scholarship Program for financial support. The authors thank Dr. Veaceslav Coropceanu, Mr. Alexandr Fonari and Mr. Stephen B. Shirring for fruitful discussions. M.A. gratefully acknowledges the financial support of the Klima- und Energiefonds Project PLASMOLED 3726090. TVT and RC were supported by NSF PREM grants DMR-0934212 and DMR-1523611.en
dc.publisherRoyal Society of Chemistry (RSC)en
dc.titleTetraaryl pyrenes: photophysical properties, computational studies, crystal structures, and application in OLEDsen
dc.typeArticleen
dc.contributor.departmentPhysical Sciences and Engineering (PSE) Divisionen
dc.contributor.departmentSolar and Photovoltaic Engineering Research Center (SPERC)en
dc.identifier.journalJ. Mater. Chem. Cen
dc.contributor.institutionDepartment of Chemistry, American University of Beirut, Beirut, Lebanonen
dc.contributor.institutionNanoTecCenter Weiz Forschungsgesellschaft MbH, Franz-Pichler-Straße 32, Weiz, Austriaen
dc.contributor.institutionDepartment of Biology and Chemistry, New Mexico Highlands University, Las Vegas, NM, United Statesen
dc.contributor.institutionDepartment of Chemistry, Center for Photochemical Sciences, Bowling Green State University, Bowling Green, OH, United Statesen
dc.contributor.institutionDepartment of Natural Sciences, Lebanese American University, Byblos, Lebanonen
dc.contributor.institutionInstitute of Solid State Physics, Graz University of Technology, Graz, Austriaen
kaust.authorBredas, Jean-Lucen
dc.relation.isSupplementedByEl-Assaad, T. H., Auer, M., Castañeda, R., Hallal, K. M., Jradi, F. M., Mosca, L., … Kaafarani, B. R. (2015). CCDC 1011328: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc12ychwen
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dc.relation.isSupplementedByHANDLE:http://hdl.handle.net/10754/624351en
dc.relation.isSupplementedByEl-Assaad, T. H., Auer, M., Castañeda, R., Hallal, K. M., Jradi, F. M., Mosca, L., … Kaafarani, B. R. (2015). CCDC 1011330: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc12yckyen
dc.relation.isSupplementedByDOI:10.5517/cc12yckyen
dc.relation.isSupplementedByHANDLE:http://hdl.handle.net/10754/624352en
dc.relation.isSupplementedByEl-Assaad, T. H., Auer, M., Castañeda, R., Hallal, K. M., Jradi, F. M., Mosca, L., … Kaafarani, B. R. (2015). CCDC 1015949: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc1335kyen
dc.relation.isSupplementedByDOI:10.5517/cc1335kyen
dc.relation.isSupplementedByHANDLE:http://hdl.handle.net/10754/624354en
dc.relation.isSupplementedByEl-Assaad, T. H., Auer, M., Castañeda, R., Hallal, K. M., Jradi, F. M., Mosca, L., … Kaafarani, B. R. (2015). CCDC 1015953: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc1335p2en
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dc.relation.isSupplementedByEl-Assaad, T. H., Auer, M., Castañeda, R., Hallal, K. M., Jradi, F. M., Mosca, L., … Kaafarani, B. R. (2015). CCDC 1039264: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc13wfn2en
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dc.relation.isSupplementedByEl-Assaad, T. H., Auer, M., Castañeda, R., Hallal, K. M., Jradi, F. M., Mosca, L., … Kaafarani, B. R. (2015). CCDC 1044326: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc141pyten
dc.relation.isSupplementedByDOI:10.5517/cc141pyten
dc.relation.isSupplementedByHANDLE:http://hdl.handle.net/10754/624397en
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