Symmetry Breaking in Side Chains Leading to Mixed Orientations and Improved Charge Transport in Isoindigo-alt-Bithiophene Based Polymer Thin Films

Xue, Guobiao; Zhao, Xikang; Qu, Ge; Xu, Tianbai; Gumyusenge, Aristide; Zhang, Zhuorui; Zhao, Yan; Diao, Ying; Li, Hanying; Mei, Jianguo

doi:10.1021/acsami.7b07624

Title: Symmetry Breaking in Side Chains Leading to Mixed Orientations and Improved Charge Transport in Isoindigo-alt-Bithiophene Based Polymer Thin Films

Journal Article · 21 July 2017 · ACS Applied Materials and Interfaces

DOI: https://doi.org/10.1021/acsami.7b07624 · OSTI ID:1397297

Xue, Guobiao ^[1]; Zhao, Xikang ^[2]; Qu, Ge ^[3]; Xu, Tianbai ^[1]; Gumyusenge, Aristide ^[2]; Zhang, Zhuorui ^[4]; Zhao, Yan ^[2];

^[5]; Li, Hanying ^[6];

^[2]

Purdue Univ., West Lafayette, IN (United States); Zhejiang Univ., Hangzhou (China)
Purdue Univ., West Lafayette, IN (United States)
Department of Chemical &, Biomolecular Engineering, University of Illinois at Urbana—Champaign, 600 South Mathews Avenue, Urbana, Illinois 61801, United States
Purdue Univ., West Lafayette, IN (United States); Tsinghua Univ., Beijing (China)
Univ. of Illinois at Urbana-Champaign, IL (United States)
Zhejiang Univ., Hangzhou (China)

The selection of side chains is important in design of conjugated polymers. It not only affects their intrinsic physical properties, but also has an impact on thin film morphologies. Recent reports suggested that a face-on/edge-on bimodal orientation observed in polymer thin films may be responsible for a three-dimensional (3D) charge transport and leads to dramatically improved mobility in donor–acceptor based conjugated polymers. To achieve a bimodal orientation in thin films has been seldom explored from the aspect of molecular design. In this work, we demonstrate a design strategy involving the use of asymmetric side chains that enables an isoindigo-based polymer to adopt a distinct bimodal orientation, confirmed by the grazing incidence X-ray diffraction. As a result, the polymer presents an average high mobility of 3.8 ± 0.7 cm² V^–1 s^–1 with a maximum value of 5.1 cm² V^–1 s^–1, in comparison with 0.47 and 0.51 cm² V^–1 s^–1 obtained from the two reference polymers. This study exemplifies a new strategy to develop the next generation polymers through understanding the property-structure relationship.

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Research Organization:: Argonne National Laboratory (ANL), Argonne, IL (United States). Advanced Photon Source (APS)

Sponsoring Organization:: US Department of the Navy, Office of Naval Research (ONR); Zhejiang University; China Scholarship Council (CSC); USDOE Office of Science (SC)

Grant/Contract Number:: N00014-16-1-2551; AC02-06CH11357

OSTI ID:: 1397297

Journal Information:: ACS Applied Materials and Interfaces, Vol. 9, Issue 30; ISSN 1944-8244

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: ENGLISH

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Cited by: 54 works

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References (41)

Integrated Materials Design of Organic Semiconductors for Field-Effect Transistors Mei, Jianguo; Diao, Ying; Appleton, Anthony L. Journal of the American Chemical Society, Vol. 135, Issue 18 https://doi.org/10.1021/ja400881n	journal	April 2013
25th Anniversary Article: Organic Field-Effect Transistors: The Path Beyond Amorphous Silicon Sirringhaus, Henning Advanced Materials, Vol. 26, Issue 9 https://doi.org/10.1002/adma.201304346	journal	January 2014
Recent Advances in Bulk Heterojunction Polymer Solar Cells Lu, Luyao; Zheng, Tianyue; Wu, Qinghe Chemical Reviews, Vol. 115, Issue 23 https://doi.org/10.1021/acs.chemrev.5b00098	journal	August 2015
Synthesis of Light-Emitting Conjugated Polymers for Applications in Electroluminescent Devices Grimsdale, Andrew C.; Leok Chan, Khai; Martin, Rainer E. Chemical Reviews, Vol. 109, Issue 3 https://doi.org/10.1021/cr000013v	journal	March 2009
25th Anniversary Article: Recent Advances in n-Type and Ambipolar Organic Field-Effect Transistors Zhao, Yan; Guo, Yunlong; Liu, Yunqi Advanced Materials, Vol. 25, Issue 38 https://doi.org/10.1002/adma.201302315	journal	August 2013
Organic Field-Effect Transistors Horowitz, Gilles Advanced Materials, Vol. 10, Issue 5 https://doi.org/10.1002/(SICI)1521-4095(199803)10:5<365::AID-ADMA365>3.0.CO;2-U	journal	March 1998
Organic thin film transistors: From theory to real devices Horowitz, Gilles Journal of Materials Research, Vol. 19, Issue 7 https://doi.org/10.1557/JMR.2004.0266	journal	July 2004
Transport in polycrystalline polymer thin-film transistors Street, R. A.; Northrup, J. E.; Salleo, A. Physical Review B, Vol. 71, Issue 16 https://doi.org/10.1103/PhysRevB.71.165202	journal	April 2005
Charge transport in polymeric transistors Salleo, Alberto Materials Today, Vol. 10, Issue 3 https://doi.org/10.1016/S1369-7021(07)70018-4	journal	March 2007
Two-dimensional charge transport in self-organized, high-mobility conjugated polymers Sirringhaus, H.; Brown, P. J.; Friend, R. H. Nature, Vol. 401, Issue 6754, p. 685-688 https://doi.org/10.1038/44359	journal	October 1999
Additions and Corrections Chemical Reviews, Vol. 107, Issue 5, p. 2165-2165 https://doi.org/10.1021/cr078022s	journal	May 2007
X-ray Scattering Study of Thin Films of Poly(2,5-bis(3-alkylthiophen-2-yl)thieno[3,2- b ]thiophene) Chabinyc, Michael L.; Toney, Michael F.; Kline, R. Joseph Journal of the American Chemical Society, Vol. 129, Issue 11 https://doi.org/10.1021/ja0670714	journal	March 2007
Observation of a Distinct Surface Molecular Orientation in Films of a High Mobility Conjugated Polymer Schuettfort, Torben; Thomsen, Lars; McNeill, Christopher R. Journal of the American Chemical Society, Vol. 135, Issue 3 https://doi.org/10.1021/ja310240q	journal	January 2013
Two-Dimensional Carrier Distribution in Top-Gate Polymer Field-Effect Transistors: Correlation between Width of Density of Localized States and Urbach Energy Kronemeijer, Auke J.; Pecunia, Vincenzo; Venkateshvaran, Deepak Advanced Materials, Vol. 26, Issue 5 https://doi.org/10.1002/adma.201303060	journal	October 2013
Siloxane-Terminated Solubilizing Side Chains: Bringing Conjugated Polymer Backbones Closer and Boosting Hole Mobilities in Thin-Film Transistors Mei, Jianguo; Kim, Do Hwan; Ayzner, Alexander L. Journal of the American Chemical Society, Vol. 133, Issue 50 https://doi.org/10.1021/ja209328m	journal	December 2011
Boosting the Ambipolar Performance of Solution-Processable Polymer Semiconductors via Hybrid Side-Chain Engineering Lee, Junghoon; Han, A-Reum; Yu, Hojeong Journal of the American Chemical Society, Vol. 135, Issue 25 https://doi.org/10.1021/ja403949g	journal	June 2013
A Balanced Face-On to Edge-On Texture Ratio in Naphthalene Diimide-Based Polymers with Hybrid Siloxane Chains Directs Highly Efficient Electron Transport Kim, Yiho; Long, Dang Xuan; Lee, Junghoon Macromolecules, Vol. 48, Issue 15 https://doi.org/10.1021/acs.macromol.5b01012	journal	July 2015
Molecular Packing of High-Mobility Diketo Pyrrolo-Pyrrole Polymer Semiconductors with Branched Alkyl Side Chains Zhang, Xinran; Richter, Lee J.; DeLongchamp, Dean M. Journal of the American Chemical Society, Vol. 133, Issue 38 https://doi.org/10.1021/ja204515s	journal	September 2011
Impact of the Crystallite Orientation Distribution on Exciton Transport in Donor–Acceptor Conjugated Polymers Ayzner, Alexander L.; Mei, Jianguo; Appleton, Anthony ACS Applied Materials & Interfaces, Vol. 7, Issue 51 https://doi.org/10.1021/acsami.5b02968	journal	August 2015
Siloxane Side Chains: A Universal Tool for Practical Applications of Organic Field-Effect Transistors Han, A-Reum; Lee, Junghoon; Lee, Hae Rang Macromolecules, Vol. 49, Issue 10 https://doi.org/10.1021/acs.macromol.6b00218	journal	May 2016
Monte Carlo simulations of charge carrier mobility in semiconducting polymer field-effect transistors Demeyu, Lemi; Stafström, Sven; Bekele, Mulugeta Physical Review B, Vol. 76, Issue 15 https://doi.org/10.1103/PhysRevB.76.155202	journal	October 2007
Dimensionality of charge transport in organic field-effect transistors Sharma, A.; van Oost, F. W. A.; Kemerink, M. Physical Review B, Vol. 85, Issue 23 https://doi.org/10.1103/PhysRevB.85.235302	journal	June 2012
Combinatorial Study of Temperature-Dependent Nanostructure and Electrical Conduction of Polymer Semiconductors: Even Bimodal Orientation Can Enhance 3D Charge Transport Park, Sangsik; Lee, Moo Hyung; Ahn, Kwang Seok Advanced Functional Materials, Vol. 26, Issue 26 https://doi.org/10.1002/adfm.201601164	journal	April 2016
Layered Distribution of Charge Carriers in Organic Thin Film Transistors Shehu, Arian; Quiroga, Santiago D.; D’Angelo, Pasquale Physical Review Letters, Vol. 104, Issue 24 https://doi.org/10.1103/PhysRevLett.104.246602	journal	June 2010
Side Chain Engineering in Solution-Processable Conjugated Polymers Mei, Jianguo; Bao, Zhenan Chemistry of Materials, Vol. 26, Issue 1 https://doi.org/10.1021/cm4020805	journal	September 2013
Influence of Alkyl Chain Branching Positions on the Hole Mobilities of Polymer Thin-Film Transistors Lei, Ting; Dou, Jin-Hu; Pei, Jian Advanced Materials, Vol. 24, Issue 48 https://doi.org/10.1002/adma.201202689	journal	September 2012
Synthesis of Isoindigo-Based Oligothiophenes for Molecular Bulk Heterojunction Solar Cells Mei, Jianguo; Graham, Kenneth R.; Stalder, Romain Organic Letters, Vol. 12, Issue 4 https://doi.org/10.1021/ol902512x	journal	February 2010
A buckling-based metrology for measuring the elastic moduli of polymeric thin films Stafford, Christopher M.; Harrison, Christopher; Beers, Kathryn L. Nature Materials, Vol. 3, Issue 8, p. 545-550 https://doi.org/10.1038/nmat1175	journal	July 2004
Melt-Processing of Complementary Semiconducting Polymer Blends for High Performance Organic Transistors Zhao, Yan; Zhao, Xikang; Roders, Michael Advanced Materials, Vol. 29, Issue 6 https://doi.org/10.1002/adma.201605056	journal	December 2016
An improved technique for determining hardness and elastic modulus using load and displacement sensing indentation experiments Oliver, W. C.; Pharr, G. M. Journal of Materials Research, Vol. 7, Issue 06, p. 1564-1583 https://doi.org/10.1557/JMR.1992.1564	journal	June 1992
Nanoindentation of polymers: an overview VanLandingham, Mark R.; Villarrubia, John S.; Guthrie, William F. Macromolecular Symposia, Vol. 167, Issue 1 https://doi.org/10.1002/1521-3900(200103)167:1<15::AID-MASY15>3.0.CO;2-T	journal	March 2001
Removal of Palladium Nanoparticles from Polymer Materials ^† Nielsen, Kim T.; Bechgaard, Klaus; Krebs, Frederik C. Macromolecules, Vol. 38, Issue 3 https://doi.org/10.1021/ma047635t	journal	February 2005
Avoid the kinks when measuring mobility McCulloch, I.; Salleo, A.; Chabinyc, M. Science, Vol. 352, Issue 6293 https://doi.org/10.1126/science.aaf9062	journal	June 2016
Strong Electron-Deficient Polymers Lead to High Electron Mobility in Air and Their Morphology-Dependent Transport Behaviors Zheng, Yu-Qing; Lei, Ting; Dou, Jin-Hu Advanced Materials, Vol. 28, Issue 33 https://doi.org/10.1002/adma.201600541	journal	June 2016
Mobility overestimation due to gated contacts in organic field-effect transistors Bittle, Emily G.; Basham, James I.; Jackson, Thomas N. Nature Communications, Vol. 7, Issue 1 https://doi.org/10.1038/ncomms10908	journal	March 2016
Electrical Instability Induced by Electron Trapping in Low-Bandgap Donor-Acceptor Polymer Field-Effect Transistors Phan, Hung; Wang, Ming; Bazan, Guillermo C. Advanced Materials, Vol. 27, Issue 43 https://doi.org/10.1002/adma.201501757	journal	October 2015
Mechanical degradation and stability of organic solar cells: molecular and microstructural determinants Savagatrup, Suchol; Printz, Adam D.; O'Connor, Timothy F. Energy & Environmental Science, Vol. 8, Issue 1 https://doi.org/10.1039/C4EE02657H	journal	January 2015
Effect of Broken Conjugation on the Stretchability of Semiconducting Polymers Savagatrup, Suchol; Zhao, Xikang; Chan, Esther Macromolecular Rapid Communications, Vol. 37, Issue 19 https://doi.org/10.1002/marc.201600377	journal	August 2016
Comparison of Methods for Determining the Mechanical Properties of Semiconducting Polymer Films for Stretchable Electronics Rodriquez, Daniel; Kim, Jae-Han; Root, Samuel E. ACS Applied Materials & Interfaces, Vol. 9, Issue 10 https://doi.org/10.1021/acsami.6b16115	journal	March 2017
Isoindigo-Based Semiconducting Polymers Using Carbosilane Side Chains for High Performance Stretchable Field-Effect Transistors Wu, Hung-Chin; Hung, Chih-Chien; Hong, Chian-Wen Macromolecules, Vol. 49, Issue 22 https://doi.org/10.1021/acs.macromol.6b02145	journal	November 2016
Inducing Elasticity through Oligo-Siloxane Crosslinks for Intrinsically Stretchable Semiconducting Polymers Wang, Ging-Ji Nathan; Shaw, Leo; Xu, Jie Advanced Functional Materials, Vol. 26, Issue 40 https://doi.org/10.1002/adfm.201602603	journal	August 2016

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