Effects of Odd–Even Side Chain Length of Alkyl-Substituted Diphenylbithiophenes on First Monolayer Thin Film Packing Structure
AuthorsAkkerman, Hylke B.
Mannsfeld, Stefan C. B.
Kaushik, Ananth P.
Zoombelt, Arjan P.
Saathoff, Jonathan D.
Toney, Michael F.
KAUST Grant NumberKUS-C1-018-02
Permanent link to this recordhttp://hdl.handle.net/10754/598081
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AbstractBecause of their preferential two-dimensional layer-by-layer growth in thin films, 5,5′bis(4-alkylphenyl)-2,2′-bithiophenes (P2TPs) are model compounds for studying the effects of systematic chemical structure variations on thin-film structure and morphology, which in turn, impact the charge transport in organic field-effect transistors. For the first time, we observed, by grazing incidence X-ray diffraction (GIXD), a strong change in molecular tilt angle in a monolayer of P2TP, depending on whether the alkyl chain on the P2TP molecules was of odd or even length. The monolayers were deposited on densely packed ultrasmooth self-assembled alkane silane modified SiO2 surfaces. Our work shows that a subtle change in molecular structure can have a significant impact on the molecular packing structure in thin film, which in turn, will have a strong impact on charge transport of organic semiconductors. This was verified by quantum-chemical calculations that predict a corresponding odd-even effect in the strength of the intermolecular electronic coupling. © 2013 American Chemical Society.
CitationAkkerman HB, Mannsfeld SCB, Kaushik AP, Verploegen E, Burnier L, et al. (2013) Effects of Odd–Even Side Chain Length of Alkyl-Substituted Diphenylbithiophenes on First Monolayer Thin Film Packing Structure. Journal of the American Chemical Society 135: 11006–11014. Available: http://dx.doi.org/10.1021/ja400015e.
SponsorsWe thank R Stoltenberg and M. LeMieux for assistance with AFM analysis. H.BA and A.P.Z. acknowledge The Netherlands Organisation for Scientific Research (NWO) for support. Portions of this research were carried out at the Stanford Synchrotron Radiation Lightsource, a Directorate of SLAC National Accelerator Laboratory and an Office of Science User Facility operated for the U.S. Department of Energy Office of Science by Stanford University. Z.B. acknowledges support provided by the National Science Foundation Solid State Chemistry (DMR 0705687-002) and Air Force Office of Scientific Research (FA 9550-12-1-0190). A.P.K. acknowledges support provided by Award No. KUS-C1-018-02, made by the King Abdullah University of Science and Technology (KAUST) to Cornell's KAUST-CU energy center. Intel Corpo. and Harvard FAS Research Computing are thanked for the provision of computing resources. S.A. and A.A.G. thank the Stanford Global Climate and Energy Project and the National Science Foundation (DMR-0820484) and Department of Energy (DE-SC0008733) as well as the Corning Foundation for their generous support.
PublisherAmerican Chemical Society (ACS)
CollectionsPublications Acknowledging KAUST Support
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