Abstract
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 language | English (US) |
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Pages (from-to) | 5792-5801 |
Number of pages | 10 |
Journal | Journal of the American Chemical Society |
Volume | 128 |
Issue number | 17 |
DOIs | |
State | Published - May 3 2006 |
ASJC Scopus subject areas
- General Chemistry
- Biochemistry
- Catalysis
- Colloid and Surface Chemistry
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CCDC 207398: Experimental Crystal Structure Determination
Facchetti, A. (Creator), Yoon, M.-H. (Creator), Stern, C. L. (Creator), Katz, H. E. (Creator) & Marks, T. J. (Creator), Cambridge Crystallographic Data Centre, 2004
DOI: 10.5517/cc6yt86, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc6yt86&sid=DataCite
Dataset
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CCDC 619629: Experimental Crystal Structure Determination
Yoon, M.-H. (Creator), Facchetti, A. (Creator), Stern, C. E. (Creator) & Marks, T. J. (Creator), Cambridge Crystallographic Data Centre, 2006
DOI: 10.5517/ccnss17, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccnss17&sid=DataCite
Dataset
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CCDC 619630: Experimental Crystal Structure Determination
Yoon, M.-H. (Creator), Facchetti, A. (Creator), Stern, C. E. (Creator) & Marks, T. J. (Creator), Cambridge Crystallographic Data Centre, 2006
DOI: 10.5517/ccnss28, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccnss28&sid=DataCite
Dataset