Dependence of crystallite formation and preferential backbone orientations on the side chain pattern in PBDTTPD polymers

Abdulrahman El Labban; Julien Warnan; Clement Cabanetos; Olivier Ratel; Christopher J. Tassone; Michael F. Toney; Pierre Beaujuge

doi:10.1021/am505280a

Dependence of crystallite formation and preferential backbone orientations on the side chain pattern in PBDTTPD polymers

Abdulrahman El Labban, Julien Warnan, Clement Cabanetos, Olivier Ratel, Christopher J. Tassone, Michael F. Toney, Pierre Beaujuge

Research output: Contribution to journal › Article › peer-review

36 Scopus citations

Abstract

(Figure Presented) Alkyl substituents appended to the π-conjugated main chain account for the solution-processability and film-forming properties of most π-conjugated polymers for organic electronic device applications, including field-effect transistors (FETs) and bulk-heterojunction (BHJ) solar cells. Beyond film-forming properties, recent work has emphasized the determining role that side-chain substituents play on polymer self-assembly and thin-film nanostructural order, and, in turn, on device performance. However, the factors that determine polymer crystallite orientation in thin-films, implying preferential backbone orientation relative to the device substrate, are a matter of some debate, and these structural changes remain difficult to anticipate. In this report, we show how systematic changes in the side-chain pattern of poly(benzo[1,2-b:4,5-b′]dithiophene-alt-thieno[3,4-c]pyrrole-4,6-dione) (PBDTTPD) polymers can (i) influence the propensity of the polymer to order in the π-stacking direction, and (ii) direct the preferential orientation of the polymer crystallites in thin films (e.g., "face-on" vs "edge-on"). Oriented crystallites, specifically crystallites that are well-ordered in the π-stacking direction, are believed to be a key contributor to improved thin-film device performance in both FETs and BHJ solar cells.

Original language	English (US)
Pages (from-to)	19477-19481
Number of pages	5
Journal	ACS Applied Materials & Interfaces
Volume	6
Issue number	22
DOIs	https://doi.org/10.1021/am505280a
State	Published - Nov 6 2014

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledged KAUST grant number(s): KUS-C1-015-21
Acknowledgements: The authors acknowledge financial support under Baseline Research Funding from King Abdullah University of Science and Technology (KAUST). Part of this work was supported by the Center for Advanced Molecular Photovoltaics (CAMP) (Award KUS-C1-015-21) made possible by King Abdullah University of Science and Technology. The authors thank KAUST Analytical Core Laboratories for mass spectrometry and elemental analyses. Portions of this research were carried out at the Stanford Synchrotron Radiation Lightsource user facility, operated by Stanford University on behalf of the U.S. Department of Energy, Office of Basic Energy Sciences.

ASJC Scopus subject areas

General Materials Science

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10.1021/am505280a

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title = "Dependence of crystallite formation and preferential backbone orientations on the side chain pattern in PBDTTPD polymers",

abstract = "(Figure Presented) Alkyl substituents appended to the π-conjugated main chain account for the solution-processability and film-forming properties of most π-conjugated polymers for organic electronic device applications, including field-effect transistors (FETs) and bulk-heterojunction (BHJ) solar cells. Beyond film-forming properties, recent work has emphasized the determining role that side-chain substituents play on polymer self-assembly and thin-film nanostructural order, and, in turn, on device performance. However, the factors that determine polymer crystallite orientation in thin-films, implying preferential backbone orientation relative to the device substrate, are a matter of some debate, and these structural changes remain difficult to anticipate. In this report, we show how systematic changes in the side-chain pattern of poly(benzo[1,2-b:4,5-b′]dithiophene-alt-thieno[3,4-c]pyrrole-4,6-dione) (PBDTTPD) polymers can (i) influence the propensity of the polymer to order in the π-stacking direction, and (ii) direct the preferential orientation of the polymer crystallites in thin films (e.g., {"}face-on{"} vs {"}edge-on{"}). Oriented crystallites, specifically crystallites that are well-ordered in the π-stacking direction, are believed to be a key contributor to improved thin-film device performance in both FETs and BHJ solar cells.",

author = "{El Labban}, Abdulrahman and Julien Warnan and Clement Cabanetos and Olivier Ratel and Tassone, {Christopher J.} and Toney, {Michael F.} and Pierre Beaujuge",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledged KAUST grant number(s): KUS-C1-015-21 Acknowledgements: The authors acknowledge financial support under Baseline Research Funding from King Abdullah University of Science and Technology (KAUST). Part of this work was supported by the Center for Advanced Molecular Photovoltaics (CAMP) (Award KUS-C1-015-21) made possible by King Abdullah University of Science and Technology. The authors thank KAUST Analytical Core Laboratories for mass spectrometry and elemental analyses. Portions of this research were carried out at the Stanford Synchrotron Radiation Lightsource user facility, operated by Stanford University on behalf of the U.S. Department of Energy, Office of Basic Energy Sciences.",

year = "2014",

month = nov,

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doi = "10.1021/am505280a",

language = "English (US)",

volume = "6",

pages = "19477--19481",

journal = "ACS Applied Materials & Interfaces",

issn = "1944-8244",

publisher = "American Chemical Society",

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T1 - Dependence of crystallite formation and preferential backbone orientations on the side chain pattern in PBDTTPD polymers

AU - El Labban, Abdulrahman

AU - Warnan, Julien

AU - Cabanetos, Clement

AU - Ratel, Olivier

AU - Tassone, Christopher J.

AU - Toney, Michael F.

AU - Beaujuge, Pierre

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledged KAUST grant number(s): KUS-C1-015-21 Acknowledgements: The authors acknowledge financial support under Baseline Research Funding from King Abdullah University of Science and Technology (KAUST). Part of this work was supported by the Center for Advanced Molecular Photovoltaics (CAMP) (Award KUS-C1-015-21) made possible by King Abdullah University of Science and Technology. The authors thank KAUST Analytical Core Laboratories for mass spectrometry and elemental analyses. Portions of this research were carried out at the Stanford Synchrotron Radiation Lightsource user facility, operated by Stanford University on behalf of the U.S. Department of Energy, Office of Basic Energy Sciences.

PY - 2014/11/6

Y1 - 2014/11/6

N2 - (Figure Presented) Alkyl substituents appended to the π-conjugated main chain account for the solution-processability and film-forming properties of most π-conjugated polymers for organic electronic device applications, including field-effect transistors (FETs) and bulk-heterojunction (BHJ) solar cells. Beyond film-forming properties, recent work has emphasized the determining role that side-chain substituents play on polymer self-assembly and thin-film nanostructural order, and, in turn, on device performance. However, the factors that determine polymer crystallite orientation in thin-films, implying preferential backbone orientation relative to the device substrate, are a matter of some debate, and these structural changes remain difficult to anticipate. In this report, we show how systematic changes in the side-chain pattern of poly(benzo[1,2-b:4,5-b′]dithiophene-alt-thieno[3,4-c]pyrrole-4,6-dione) (PBDTTPD) polymers can (i) influence the propensity of the polymer to order in the π-stacking direction, and (ii) direct the preferential orientation of the polymer crystallites in thin films (e.g., "face-on" vs "edge-on"). Oriented crystallites, specifically crystallites that are well-ordered in the π-stacking direction, are believed to be a key contributor to improved thin-film device performance in both FETs and BHJ solar cells.

AB - (Figure Presented) Alkyl substituents appended to the π-conjugated main chain account for the solution-processability and film-forming properties of most π-conjugated polymers for organic electronic device applications, including field-effect transistors (FETs) and bulk-heterojunction (BHJ) solar cells. Beyond film-forming properties, recent work has emphasized the determining role that side-chain substituents play on polymer self-assembly and thin-film nanostructural order, and, in turn, on device performance. However, the factors that determine polymer crystallite orientation in thin-films, implying preferential backbone orientation relative to the device substrate, are a matter of some debate, and these structural changes remain difficult to anticipate. In this report, we show how systematic changes in the side-chain pattern of poly(benzo[1,2-b:4,5-b′]dithiophene-alt-thieno[3,4-c]pyrrole-4,6-dione) (PBDTTPD) polymers can (i) influence the propensity of the polymer to order in the π-stacking direction, and (ii) direct the preferential orientation of the polymer crystallites in thin films (e.g., "face-on" vs "edge-on"). Oriented crystallites, specifically crystallites that are well-ordered in the π-stacking direction, are believed to be a key contributor to improved thin-film device performance in both FETs and BHJ solar cells.

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UR - https://pubs.acs.org/doi/10.1021/am505280a

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U2 - 10.1021/am505280a

DO - 10.1021/am505280a

M3 - Article

C2 - 25347287

SN - 1944-8244

VL - 6

SP - 19477

EP - 19481

JO - ACS Applied Materials & Interfaces

JF - ACS Applied Materials & Interfaces

IS - 22

ER -

Dependence of crystallite formation and preferential backbone orientations on the side chain pattern in PBDTTPD polymers

Abstract

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