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Anthracene Derivatives Substituted with Phenyl or Pentafluorophenyl for Organic Thin Film Transistors

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Four anthracene derivatives (TIPSAntP, TIPSAntFP, TIPSAntPA and TIPSAntFPA) containing phenyl or pentafluorophenyl have been synthesized by using Suzuki coupling or Sonogashira cross-coupling reactions. DSC measurement showed that TIPSAntP and TIPSAntFP were crystalline and thermally stable to 300 °C under nitrogen atmosphere, comparing to TIPSAntPA and TIPSAntFPA with acetylene. From cyclic voltammetry measurement, it can be observed that all compounds were electrochemically stable in the voltage range of −2.0∼2.0 V. The obtained data revealed that fluorinated phenyl groups could decrease HOMO as well as LUMO levels of the compounds. UV-vis absorption and fluorescent emission spectra of them showed red shift in solid film state in comparison to their solution state, revealing that the molecular packing formed in solid state. Further proofs for the study of the packing order of crystals by X-ray analysis showed that phenyl groups provided TIPSAntP and TIPSAntPA planar conjugated unit along the anthracene core and favorable face-to-face interactions between their neighboring molecules. Fluorinated phenyl groups were twisted to the anthracene core and formed interleaved layer packing in TIPSAntFP. Preliminary device results were achieved from TIPSAntP and TIPSAntPA with p-type mobility of 10−5 and ∼10−6 cm2/V · s, respectively, and n-type mobility for TIPSAntFP as ∼10−7 cm2/V · s.
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Document Type: Research Article

Publication date: 2011-05-01

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  • Journal for Nanoscience and Nanotechnology (JNN) is an international and multidisciplinary peer-reviewed journal with a wide-ranging coverage, consolidating research activities in all areas of nanoscience and nanotechnology into a single and unique reference source. JNN is the first cross-disciplinary journal to publish original full research articles, rapid communications of important new scientific and technological findings, timely state-of-the-art reviews with author's photo and short biography, and current research news encompassing the fundamental and applied research in all disciplines of science, engineering and medicine.
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