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Synthesis of Monochlorosilyl Derivatives of Dialkyloligothiophenes for Self-Assembling Monolayer 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, and Aziz M. Muzafarov, Washington (2010)

Unsymmetrical dimethylchlorosilyl-substituted α,α′-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 SiO2 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 cm2/(V s) and an on/off ratio up to 1 × 108.

Partners : Philips, RuG

Place of Publication : Washington

Date of Publication : 2010/09/03

Additional Data : Organometallics 2010, 29, 4213–4226

Link to the online version of the article.