Phosphorus-based heteropentacenes: Efficiently tunable materials for organic n-type semiconductors

Yvonne Dienes, Matthias Eggenstein, T. Kárpáti, Todd C. Sutherland, L. Nyulászi, Thomas Baumgartner

Research output: Contribution to journalArticle

103 Citations (Scopus)

Abstract

Benzo-condensed dithieno[3,2-b:2',3'-d]phospholes have been synthesized that allow convenient tuning of properties that are essential for application as semiconductor materials in organic field-effect transistor (OFET) devices. The versatile reactivity of the trivalent phosphorus atom in these heteropentacenes provides access to a series of materials that show different photophysical properties, significantly different organization in the solid state, and distinctly different electrochemical properties that can be achieved by simple chemical modifications. The materials show strong photoluminescence in solution and in the solid state that depends on the electronic nature of the phosphorus center. Electrochemical studies revealed that the phosphorus atom intrinsically furnishes materials with n-channel or ambipolar behavior, also depending on its electronic nature. The experimental data were verified by DFT quantum chemical calculations and suggest that the phosphorus-based heteropentacenes could be excellent candidates for n-channel OFET semiconductor materials.

Original languageEnglish
Pages (from-to)9878-9889
Number of pages12
JournalChemistry - A European Journal
Volume14
Issue number32
DOIs
Publication statusPublished - Nov 10 2008

Fingerprint

Phosphorus
Semiconductor materials
Organic field effect transistors
Atoms
Chemical modification
Electrochemical properties
Discrete Fourier transforms
Photoluminescence
Tuning

Keywords

  • Density functional calculations
  • Luminescence
  • Phosphorus heterocycles
  • Semiconductors
  • Sulfur heterocycles

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Phosphorus-based heteropentacenes : Efficiently tunable materials for organic n-type semiconductors. / Dienes, Yvonne; Eggenstein, Matthias; Kárpáti, T.; Sutherland, Todd C.; Nyulászi, L.; Baumgartner, Thomas.

In: Chemistry - A European Journal, Vol. 14, No. 32, 10.11.2008, p. 9878-9889.

Research output: Contribution to journalArticle

Dienes, Yvonne ; Eggenstein, Matthias ; Kárpáti, T. ; Sutherland, Todd C. ; Nyulászi, L. ; Baumgartner, Thomas. / Phosphorus-based heteropentacenes : Efficiently tunable materials for organic n-type semiconductors. In: Chemistry - A European Journal. 2008 ; Vol. 14, No. 32. pp. 9878-9889.
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