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
Aziz M. Muzafarov
10.1021/om100139y.s001
https://acs.figshare.com/articles/journal_contribution/Synthesis_of_Monochlorosilyl_Derivatives_of_Dialkyloligothiophenes_for_Self_Assembling_Monolayer_Field_Effect_Transistors/2723251
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 SiO<sub>2</sub> 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<sup>2</sup>/(V s) and an on/off ratio up to 1 × 10<sup>8</sup>.
2010-10-11 00:00:00
DCI MS techniques
hydrosilylation
oligothiophene
nonreactive byproducts
dielectric hydroxylated SiO 2 surfaces
form semiconducting monolayers
NMR
SAM
SAMFET