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Issue 8, 2013
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Bis(carbazolyl) derivatives of pyrene and tetrahydropyrene: synthesis, structures, optical properties, electrochemistry, and electroluminescence

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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 → S1 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.

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

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Publication details

The article was received on 23 Oct 2012, accepted on 29 Dec 2012 and first published on 08 Jan 2013


Article type: Paper
DOI: 10.1039/C2TC00474G
Citation: J. Mater. Chem. C, 2013,1, 1638-1650
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    Bis(carbazolyl) derivatives of pyrene and tetrahydropyrene: synthesis, structures, optical properties, electrochemistry, and electroluminescence

    B. R. Kaafarani, A. O. El-Ballouli, R. Trattnig, A. Fonari, S. Sax, B. Wex, C. Risko, R. S. Khnayzer, S. Barlow, D. Patra, T. V. Timofeeva, E. J. W. List, J. Brédas and S. R. Marder, J. Mater. Chem. C, 2013, 1, 1638
    DOI: 10.1039/C2TC00474G

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