Synthesis and characterization of diperfluorooctyl-substituted phenylene-thiophene oligomers as n-type semiconductors. Molecular structure-film microstructure-mobility relationships, organic field-effect transistors, and transistor nonvolatile memory elements

Antonio Facchetti, Joseph Letizia, Myung Han Yoon, Melissa Mushrush, Howard E. Katz, Tobin J. Marks

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Abstract

A new series of mixed phenylene-thiophene oligomers with terminal n-perfluorooctyl groups has been synthesized. These compounds are 2,5-bis(4-n-perfluorooctylphenyl)-thiophene (DFO-PTP, 1), 5,5′-bis(4-n- perfluorooctylphenyl)-2,2′-bithiophene (DFO-PTTP, 2), 5,5″-bis(4-n- perfluorooctylphenyl)-2,2′:5′,2″-terthiophene (DFO-PT 3P, 3), 5,5‴-bis(4-n-perfluorooctylphenyl)-2,2′: 5′,2″:5″,2‴-quaterthiophene (DFO-PT4P, 4), and 1,4-bis[5-(4-n-perfluorooctylphenyl)-2-thienyl]benzene (DH-PTPTP, 5). These systems have been characterized by 1H and 19F NMR, elemental analysis or HRMS, optical absorption and emission spectroscopies, differential scanning calorimetry, and thermogravimetric analysis. Vacuum-deposited films were characterized by optical absorption and emission spectroscopy, X-ray diffraction, scanning electron microscopy, and field effect transistor measurements. As thin films, all of the fluorinated compounds are n-type semiconductors with carrier mobilities ranging from ∼ 10-6 to ∼ 0.1 cm2 V-1 s-1, depending on the substrate deposition temperature. Furthermore, these films exhibit very large current Ion:Ioff ratios (up to ∼ 107) due to substantially suppressed off-currents. Particularly interesting is straightforwardly synthesized DFO-PTTP (2), which displays a combination of high mobility, high current Ion:Ioff ratio, and reversible, tunable, and stable memory effects.

Original languageEnglish
Pages (from-to)4715-4727
Number of pages13
JournalChemistry of Materials
Volume16
Issue number23
DOIs
Publication statusPublished - Nov 16 2004

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ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)
  • Materials Chemistry

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