Fluorocarbon-modified organic semiconductors: Molecular architecture, electronic, and crystal structure tuning of arene- versus fluoroarene-thiophene oligomer thin-film properties

Myung Han Yoon, Antonio Facchetti, Charlotte E. Stern, Tobin J. Marks

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275 Citations (Scopus)


We present here the systematic synthesis and comparative physicochemical characterization of a series of regiochemically varied and core size extension-modulated arene(perfluoroarene)-thiophene oligomers. The molecules investigated are: 5,5″-diphenyl-2,2′:5′,2″:5″, 2‴-quaterthiophene (1), 5,5′-bis-{1-[4-(thien-2-yl)phenyl]}-2, 2′-dithiophene (2), 4,4′-bis[5-(2,2′-dithiophenyl)]-biphenyl (3), 5,5″-diperfluorophenyl-2,2′:5′,2″:5″, 2‴-quaterthiophene (4), 5,5′-bis{1-[4-(thien-2-yl)perfluorophenyl]} -2,2′-dithiophene (5), 4,4′-bis[5-(2,2′-dithiophenyl)]- perfluorobiphenyl (6), 5,5″-diperfluorophenyl-2,2′:5′, 2″-tertthiophene (7), 5,5′-diperfluorophenyl-2,2′-dihiophene (8), and 5,5-diperfluorophenylthiophene (9). Trends in optical absorption and emission parameters, molecular structures as defined by single-crystal X-ray diffraction, as well as electrochemical redox processes are described. The morphologies and microstructures of the vapor-deposited films grown over a range of growth temperatures have also been characterized. Field-effect transistor (FET) measurements demonstrate that all of these materials are FET-active and, depending on the molecular architecture, exhibit comparably good p- or n-type mobility when optimum film microstructural order is achieved. A very large n-channel mobility of ∼0.5 cm2/Vs with Ion/I off ratios > 108 is achieved for films of 4.

Original languageEnglish
Pages (from-to)5792-5801
Number of pages10
JournalJournal of the American Chemical Society
Issue number17
Publication statusPublished - May 3 2006


ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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