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

doi:10.1039/C5TC02849C

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 language	English (US)
Pages (from-to)	3041-3058
Number of pages	18
Journal	J. Mater. Chem. C
Volume	4
Issue number	14
DOIs	https://doi.org/10.1039/C5TC02849C
State	Published - 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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10.1039/C5TC02849C

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El-Assaad, T. H., Auer, M., Castañeda, R., Hallal, K. M., Jradi, F. M., Mosca, L., Khnayzer, R. S., Patra, D., Timofeeva, T. V., Bredas, J.-L., List-Kratochvil, E. J. W., Wex, B., & Kaafarani, B. R. (2016). Tetraaryl pyrenes: photophysical properties, computational studies, crystal structures, and application in OLEDs. J. Mater. Chem. C, 4(14), 3041-3058. https://doi.org/10.1039/C5TC02849C

@article{9ea3b0699b254ab2b259294f78582cde,

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

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. {\textcopyright} The Royal Society of Chemistry 2016.",

author = "El-Assaad, {Tarek H.} and Manuel Auer and Raul Casta{\~n}eda and Hallal, {Kassem M.} and Jradi, {Fadi M.} and Lorenzo Mosca and Khnayzer, {Rony S.} and Digambara Patra and Timofeeva, {Tatiana V.} and Jean-Luc Bredas and List-Kratochvil, {Emil J. W.} and Brigitte Wex and Kaafarani, {Bilal R.}",

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.",

year = "2016",

doi = "10.1039/C5TC02849C",

language = "English (US)",

volume = "4",

pages = "3041--3058",

journal = "J. Mater. Chem. C",

issn = "2050-7526",

publisher = "Royal Society of Chemistry",

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}

El-Assaad, TH, Auer, M, Castañeda, R, Hallal, KM, Jradi, FM, Mosca, L, Khnayzer, RS, Patra, D, Timofeeva, TV, Bredas, J-L, List-Kratochvil, EJW, Wex, B & Kaafarani, BR 2016, 'Tetraaryl pyrenes: photophysical properties, computational studies, crystal structures, and application in OLEDs', J. Mater. Chem. C, vol. 4, no. 14, pp. 3041-3058. https://doi.org/10.1039/C5TC02849C

TY - JOUR

T1 - Tetraaryl pyrenes: photophysical properties, computational studies, crystal structures, and application in OLEDs

AU - El-Assaad, Tarek H.

AU - Auer, Manuel

AU - Castañeda, Raul

AU - Hallal, Kassem M.

AU - Jradi, Fadi M.

AU - Mosca, Lorenzo

AU - Khnayzer, Rony S.

AU - Patra, Digambara

AU - Timofeeva, Tatiana V.

AU - Bredas, Jean-Luc

AU - List-Kratochvil, Emil J. W.

AU - Wex, Brigitte

AU - Kaafarani, Bilal R.

N1 - 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.

PY - 2016

Y1 - 2016

N2 - 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.

AB - 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.

UR - http://hdl.handle.net/10754/621615

UR - http://xlink.rsc.org/?DOI=C5TC02849C

UR - http://www.scopus.com/inward/record.url?scp=84963820953&partnerID=8YFLogxK

U2 - 10.1039/C5TC02849C

DO - 10.1039/C5TC02849C

M3 - Article

SN - 2050-7526

VL - 4

SP - 3041

EP - 3058

JO - J. Mater. Chem. C

JF - J. Mater. Chem. C

IS - 14

ER -

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

Abstract

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CCDC 1039264: Experimental Crystal Structure Determination : 2,2',2'',2'''-pyrene-1,3,6,8-tetrayltetrathiophene

CCDC 1015949: Experimental Crystal Structure Determination : 1,3,6,8-tetrakis(3,5-bis(trifluoromethyl)phenyl)pyrene

CCDC 1044326: Experimental Crystal Structure Determination : 1,3,6,8-tetrakis(4-t-butylphenyl)pyrene

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

Abstract

Bibliographical note

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Datasets

CCDC 1039264: Experimental Crystal Structure Determination : 2,2',2'',2'''-pyrene-1,3,6,8-tetrayltetrathiophene

CCDC 1015949: Experimental Crystal Structure Determination : 1,3,6,8-tetrakis(3,5-bis(trifluoromethyl)phenyl)pyrene

CCDC 1044326: Experimental Crystal Structure Determination : 1,3,6,8-tetrakis(4-t-butylphenyl)pyrene

Cite this