Synthesis of Monochlorosilyl Derivatives of Dialkyloligothiophenes for Self-Assembling Mono layer Field-Effect Transistors

Sergei A. Ponomarenko*, Oleg V. Borshchev, Timo Meyer-Friedrichsen, Alexandra P. Pleshkova, Sepas Setayesh, Edsger C. P. Smits, Simon G. J. Mathijssen, Dago M. de Leeuw, Stephan Kirchmeyer, Aziz M. Muzafarov

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

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Abstract

Unsymmetrical dimethylchlorosilyl-substituted alpha,alpha'-dialkylquater-, quinque-, and sexithiophenes were designed and successfully synthesized by a combination of Kumada and Suzuki cross-coupling reactions followed by hydrosilylation. Optimization possibilities of the hydrosilylation of low-soluble linear oligothiophenes by dimethylchlorosilane as well as the nonreactive byproducts formed are described. The molecular structures of the obtained dimethylchlorosilyl-functionalized oligothiophenes were proven by NMR and DCI MS techniques. These compounds were found to be stable and reactive enough, even in the presence of the nonreactive byproducts, to form semiconducting monolayers on dielectric hydroxylated SiO(2) surfaces by self-assembly from solution. The semiconducting properties of these oligothiophene SAMs were as good as those of bulk oligothiophenes. This allowed the production of stable, even under ambient conditions, SAMFETs with a mobility of up to 0.04 cm(2)/(V s) and an on/off ratio up to 1 x 10(8).

Original languageEnglish
Pages (from-to)4213-4226
Number of pages14
JournalOrganometallics
Volume29
Issue number19
DOIs
Publication statusPublished - 11-Oct-2010

Keywords

  • THIN-FILM TRANSISTORS
  • ORGANIC INTEGRATED-CIRCUITS
  • ATOMIC-FORCE MICROSCOPY
  • MECHANICAL-PROPERTIES
  • TRANSPORT-PROPERTIES
  • OPTICAL-PROPERTIES
  • CONJUGATED THIOLS
  • MOLECULAR PACKING
  • OLIGOTHIOPHENES
  • MONOLAYER

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