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

Tarek H. El-Assaad, Manuel Auer, Raul Castañeda, Kassem M. Hallal, Fadi M. Jradi, Lorenzo Mosca, Rony S. Khnayzer, Digambara Patra, Tatiana V. Timofeeva, Jean-Luc Bredas, Emil J. W. List-Kratochvil, Brigitte Wex, Bilal R. Kaafarani

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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.
Original languageEnglish (US)
Pages (from-to)3041-3058
Number of pages18
JournalJ. Mater. Chem. C
Volume4
Issue number14
DOIs
StatePublished - 2016

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: 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.

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  • CCDC 1015953: Experimental Crystal Structure Determination : 1,3,6,8-tetrakis(4-phenoxyphenyl)pyrene

    El-Assaad, T. H. (Creator), Auer, M. (Creator), Castañeda, R. (Creator), Hallal, K. M. (Creator), Jradi, F. M. (Creator), Mosca, L. (Creator), Khnayzer, R. S. (Creator), Patra, D. (Creator), Timofeeva, T. V. (Creator), Bredas, J. (Creator), List-Kratochvil, E. J. W. (Creator), Wex, B. (Creator), Kaafarani, B. R. (Creator), El-Assaad, T. H. (Creator), Auer, M. (Creator), Castañeda, R. (Creator), Hallal, K. M. (Creator), Jradi, F. M. (Creator), Mosca, L. (Creator), Khnayzer, R. S. (Creator), Patra, D. (Creator), Timofeeva, T. V. (Creator), List-Kratochvil, E. J. W. (Creator), Wex, B. (Creator) & Kaafarani, B. R. (Creator), Cambridge Crystallographic Data Centre, Oct 15 2015

    Dataset

  • CCDC 1011328: Experimental Crystal Structure Determination : 1,3,6,8-tetrakis(4-(methylsulfanyl)phenyl)pyrene

    El-Assaad, T. H. (Creator), Auer, M. (Creator), Castañeda, R. (Creator), Hallal, K. M. (Creator), Jradi, F. M. (Creator), Mosca, L. (Creator), Khnayzer, R. S. (Creator), Patra, D. (Creator), Timofeeva, T. V. (Creator), Bredas, J. (Creator), List-Kratochvil, E. J. W. (Creator), Wex, B. (Creator), Kaafarani, B. R. (Creator), El-Assaad, T. H. (Creator), Auer, M. (Creator), Castañeda, R. (Creator), Hallal, K. M. (Creator), Jradi, F. M. (Creator), Mosca, L. (Creator), Khnayzer, R. S. (Creator), Patra, D. (Creator), Timofeeva, T. V. (Creator), List-Kratochvil, E. J. W. (Creator), Wex, B. (Creator) & Kaafarani, B. R. (Creator), Cambridge Crystallographic Data Centre, Oct 15 2015

    Dataset

  • CCDC 1011330: Experimental Crystal Structure Determination : 1,3,6,8-tetrakis(4-fluorophenyl)pyrene

    El-Assaad, T. H. (Creator), Auer, M. (Creator), Castañeda, R. (Creator), Hallal, K. M. (Creator), Jradi, F. M. (Creator), Mosca, L. (Creator), Khnayzer, R. S. (Creator), Patra, D. (Creator), Timofeeva, T. V. (Creator), Bredas, J. (Creator), List-Kratochvil, E. J. W. (Creator), Wex, B. (Creator), Kaafarani, B. R. (Creator), El-Assaad, T. H. (Creator), Auer, M. (Creator), Castañeda, R. (Creator), Hallal, K. M. (Creator), Jradi, F. M. (Creator), Mosca, L. (Creator), Khnayzer, R. S. (Creator), Patra, D. (Creator), Timofeeva, T. V. (Creator), List-Kratochvil, E. J. W. (Creator), Wex, B. (Creator) & Kaafarani, B. R. (Creator), Cambridge Crystallographic Data Centre, Oct 15 2015

    Dataset

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