Tuning the charge-transport parameters of perylene diimide single crystals via end and/or core functionalization: A density functional theory investigation

M. Carmen Ruiz Delgado, Eung Gun Kim, Demétrio A. Da Silva Filho, Jean-Luc Bredas*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

271 Scopus citations

Abstract

Perylene tetracarboxylic diimide (PTCDI) derivatives stand out as one of the most investigated families of air-stable n-type organic semiconductors for organic 2hin-film transistors. Here, we use density functional theory to illustrate how it is possible to control the charge-transport parameters of PTCDIs as a function of the type, number, and positions of the substituents. Specifically, two strategies of functionalization related to core and end substitutions are investigated. While end-substituted PTCDIs present the same functional molecular backbone, their molecular packing in the crystal significantly varies; as a consequence, this series of derivatives constitutes an ideal test bed to evaluate the models that describe charge-transport in organic semiconductors. Our results indicate that large bandwidths along with small effective masses can be obtained with the insertion of appropriate substituents on the nitrogens, in particular halogenated aromatic groups.

Original languageEnglish (US)
Pages (from-to)3375-3387
Number of pages13
JournalJournal of the American Chemical Society
Volume132
Issue number10
DOIs
StatePublished - Mar 17 2010

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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