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

73 Scopus citations

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 → 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 (US)
Pages (from-to)1638-1650
Number of pages13
JournalJournal of Materials Chemistry C
Volume1
Issue number8
DOIs
StatePublished - Feb 28 2013
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)
  • Materials Chemistry

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