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

Hylke B. Akkerman; Stefan C. B. Mannsfeld; Ananth P. Kaushik; Eric Verploegen; Luc Burnier; Arjan P. Zoombelt; Jonathan D. Saathoff; Sanghyun Hong; Sule Atahan-Evrenk; Xueliang Liu; Alán Aspuru-Guzik; Michael F. Toney; Paulette Clancy; Zhenan Bao

doi:10.1021/ja400015e

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

Hylke B. Akkerman, Stefan C. B. Mannsfeld, Ananth P. Kaushik, Eric Verploegen, Luc Burnier, Arjan P. Zoombelt, Jonathan D. Saathoff, Sanghyun Hong, Sule Atahan-Evrenk, Xueliang Liu, Alán Aspuru-Guzik, Michael F. Toney, Paulette Clancy, Zhenan Bao

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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.

Original language	English (US)
Pages (from-to)	11006-11014
Number of pages	9
Journal	Journal of the American Chemical Society
Volume	135
Issue number	30
DOIs	https://doi.org/10.1021/ja400015e
State	Published - Jul 22 2013
Externally published	Yes

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledged KAUST grant number(s): KUS-C1-018-02
Acknowledgements: 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.
This publication acknowledges KAUST support, but has no KAUST affiliated authors.

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Akkerman, H. B., Mannsfeld, S. C. B., Kaushik, A. P., Verploegen, E., Burnier, L., Zoombelt, A. P., Saathoff, J. D., Hong, S., Atahan-Evrenk, S., Liu, X., Aspuru-Guzik, A., Toney, M. F., Clancy, P., & Bao, Z. (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(30), 11006-11014. https://doi.org/10.1021/ja400015e

@article{eeb99418ee62465dae8a0da6596909dd,

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

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. {\textcopyright} 2013 American Chemical Society.",

author = "Akkerman, {Hylke B.} and Mannsfeld, {Stefan C. B.} and Kaushik, {Ananth P.} and Eric Verploegen and Luc Burnier and Zoombelt, {Arjan P.} and Saathoff, {Jonathan D.} and Sanghyun Hong and Sule Atahan-Evrenk and Xueliang Liu and Al{\'a}n Aspuru-Guzik and Toney, {Michael F.} and Paulette Clancy and Zhenan Bao",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledged KAUST grant number(s): KUS-C1-018-02 Acknowledgements: 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. This publication acknowledges KAUST support, but has no KAUST affiliated authors.",

year = "2013",

month = jul,

day = "22",

doi = "10.1021/ja400015e",

language = "English (US)",

volume = "135",

pages = "11006--11014",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "30",

}

Akkerman, HB, Mannsfeld, SCB, Kaushik, AP, Verploegen, E, Burnier, L, Zoombelt, AP, Saathoff, JD, Hong, S, Atahan-Evrenk, S, Liu, X, Aspuru-Guzik, A, Toney, MF, Clancy, P & Bao, Z 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, vol. 135, no. 30, pp. 11006-11014. https://doi.org/10.1021/ja400015e

TY - JOUR

T1 - Effects of Odd–Even Side Chain Length of Alkyl-Substituted Diphenylbithiophenes on First Monolayer Thin Film Packing Structure

AU - Akkerman, Hylke B.

AU - Mannsfeld, Stefan C. B.

AU - Kaushik, Ananth P.

AU - Verploegen, Eric

AU - Burnier, Luc

AU - Zoombelt, Arjan P.

AU - Saathoff, Jonathan D.

AU - Hong, Sanghyun

AU - Atahan-Evrenk, Sule

AU - Liu, Xueliang

AU - Aspuru-Guzik, Alán

AU - Toney, Michael F.

AU - Clancy, Paulette

AU - Bao, Zhenan

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledged KAUST grant number(s): KUS-C1-018-02 Acknowledgements: 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. This publication acknowledges KAUST support, but has no KAUST affiliated authors.

PY - 2013/7/22

Y1 - 2013/7/22

N2 - 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.

AB - 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.

UR - http://hdl.handle.net/10754/598081

UR - https://pubs.acs.org/doi/10.1021/ja400015e

UR - http://www.scopus.com/inward/record.url?scp=84881071687&partnerID=8YFLogxK

U2 - 10.1021/ja400015e

DO - 10.1021/ja400015e

M3 - Article

C2 - 23822850

SN - 0002-7863

VL - 135

SP - 11006

EP - 11014

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 30

ER -

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

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