A. Facchetti, Joseph A. Letizia, Myung‐Han Yoon
Sep 4, 2004
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Chemistry of Materials
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−PT3P, 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...