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

Bilal R. Kaafarani, Ala'A O. El-Ballouli, Roman Trattnig, Alexandr Fonari, Stefan Sax, Brigitte Wex, Chad Risko, Rony S. Khnayzer, Stephen Barlow, Digambara Patra, Tatiana V. Timofeeva, Emil J.W. List, Jean Luc Brédas, Seth R. Marder

Research output: Contribution to journalArticlepeer-review

80 Scopus citations


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.

Original languageEnglish
Pages (from-to)1638-1650
Number of pages13
JournalJournal of Materials Chemistry C
Issue number8
StatePublished - Feb 28 2013

Bibliographical note

Funding Information:
The authors gratefully acknowledge the young people who participated in the fOllow-up study. Birgitta Melander was imtrumental in assuring complete coverageoftheoriginalcohortofprobandsandcontrols. Theworkwassupported by grants from the Swedish Social Research Council, the Swedish Medical Research Council, the Sunnerdahl Foundation and the Sven jerring Foundation.

ASJC Scopus subject areas

  • Chemistry (all)
  • Materials Chemistry


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