Rubrenes: Planar and twisted

Abhimanyu S. Paraskar, A. Ravikumar Reddy, Asit Patra, Yair H. Wijsboom, Ori Gidron, Linda J.W. Shimon, Gregory Leitus, Michael Bendikov

Research output: Contribution to journalArticle

95 Citations (Scopus)

Abstract

Surprisingly, despite its very high mobility in a single crystal, rubrene shows very low mobility in vacuum-sublimed or solution-processed organic thin-film transistors. We synthesized several rubrene analogues with electron-withdrawing and electron-donating substituents and found that most of the substituted rubrenes are not planar in the solid state. Moreover, we conclude (based on experimental and calculated data) that even parent rubrene is not planar in solution and in thin films. This discovery explains why high mobility is reported in rubrene single crystals, but rubreneshows very low field-effect mobility in thin films. The substituted rubrenes obtained in this work have significantly better solubility than parent rubrene and some even form films and not crystals after evaporation of the solvent. Thus, substituted rubrenes are promising materials for organic light-emitting diode (OLED) applications.

Original languageEnglish
Pages (from-to)10639-10647
Number of pages9
JournalChemistry - A European Journal
Volume14
Issue number34
DOIs
Publication statusPublished - Nov 26 2008

Keywords

  • Field-effect transistors
  • Materials science
  • Organic electronic materials
  • Rubrenes
  • Substituent effects

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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    Paraskar, A. S., Ravikumar Reddy, A., Patra, A., Wijsboom, Y. H., Gidron, O., Shimon, L. J. W., Leitus, G., & Bendikov, M. (2008). Rubrenes: Planar and twisted. Chemistry - A European Journal, 14(34), 10639-10647. https://doi.org/10.1002/chem.200800802