Effects of Odd–Even Side Chain Length of Alkyl-Substituted Diphenylbithiophenes on First Monolayer Thin Film Packing Structure

Handle URI:
http://hdl.handle.net/10754/598081
Title:
Effects of Odd–Even Side Chain Length of Alkyl-Substituted Diphenylbithiophenes on First Monolayer Thin Film Packing Structure
Authors:
Akkerman, Hylke B.; Mannsfeld, Stefan C. B.; Kaushik, Ananth P.; Verploegen, Eric; Burnier, Luc; Zoombelt, Arjan P.; Saathoff, Jonathan D.; Hong, Sanghyun; Atahan-Evrenk, Sule; Liu, Xueliang; Aspuru-Guzik, Alán; Toney, Michael F.; Clancy, Paulette; Bao, Zhenan
Abstract:
Because 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.
Citation:
Akkerman 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.
Publisher:
American Chemical Society (ACS)
Journal:
Journal of the American Chemical Society
KAUST Grant Number:
KUS-C1-018-02
Issue Date:
31-Jul-2013
DOI:
10.1021/ja400015e
PubMed ID:
23822850
Type:
Article
ISSN:
0002-7863; 1520-5126
Sponsors:
We 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.
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Publications Acknowledging KAUST Support

Full metadata record

DC FieldValue Language
dc.contributor.authorAkkerman, Hylke B.en
dc.contributor.authorMannsfeld, Stefan C. B.en
dc.contributor.authorKaushik, Ananth P.en
dc.contributor.authorVerploegen, Ericen
dc.contributor.authorBurnier, Lucen
dc.contributor.authorZoombelt, Arjan P.en
dc.contributor.authorSaathoff, Jonathan D.en
dc.contributor.authorHong, Sanghyunen
dc.contributor.authorAtahan-Evrenk, Suleen
dc.contributor.authorLiu, Xueliangen
dc.contributor.authorAspuru-Guzik, Alánen
dc.contributor.authorToney, Michael F.en
dc.contributor.authorClancy, Pauletteen
dc.contributor.authorBao, Zhenanen
dc.date.accessioned2016-02-25T13:12:18Zen
dc.date.available2016-02-25T13:12:18Zen
dc.date.issued2013-07-31en
dc.identifier.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.en
dc.identifier.issn0002-7863en
dc.identifier.issn1520-5126en
dc.identifier.pmid23822850en
dc.identifier.doi10.1021/ja400015een
dc.identifier.urihttp://hdl.handle.net/10754/598081en
dc.description.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.en
dc.description.sponsorshipWe 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.en
dc.publisherAmerican Chemical Society (ACS)en
dc.titleEffects of Odd–Even Side Chain Length of Alkyl-Substituted Diphenylbithiophenes on First Monolayer Thin Film Packing Structureen
dc.typeArticleen
dc.identifier.journalJournal of the American Chemical Societyen
dc.contributor.institutionStanford University, Palo Alto, United Statesen
dc.contributor.institutionStanford Synchrotron Radiation Laboratory, Menlo Park, United Statesen
dc.contributor.institutionCornell University, Ithaca, United Statesen
dc.contributor.institutionHarvard University, Cambridge, United Statesen
dc.contributor.institutionSamsung Cheil Industries, , South Koreaen
dc.contributor.institutionHolst Centre, Eindhoven, Netherlandsen
kaust.grant.numberKUS-C1-018-02en

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