Tuning conformation, assembly, and charge transport properties of conjugated polymers by printing flow

Park, Kyung Sun; Kwok, Justin J.; Dilmurat, Rishat; Qu, Ge; Kafle, Prapti; Luo, Xuyi; Jung, Seok-Heon; Olivier, Yoann; Lee, Jin-Kyun; Mei, Jianguo; Beljonne, David; Diao, Ying

doi:10.1126/sciadv.aaw7757

Tuning conformation, assembly, and charge transport properties of conjugated polymers by printing flow

Journal Article · Fri Aug 02 00:00:00 EDT 2019 · Science Advances

DOI:https://doi.org/10.1126/sciadv.aaw7757· OSTI ID:1600813

^[1]; ^[1]; ^[2]; Qu, Ge ^[1]; ^[1]; ^[3]; ^[4]; ^[2]; Lee, Jin-Kyun ^[4]; ^[3]; Beljonne, David ^[2]; ^[1]

Univ. of Illinois at Urbana-Champaign, IL (United States)
Univ. of Mons (Belgium)
Purdue Univ., West Lafayette, IN (United States)
Inha Univ. (South Korea)

Intrachain charge transport is unique to conjugated polymers distinct from inorganic and small molecular semiconductors and is key to achieving high-performance organic electronics. Polymer backbone planarity and thin film morphology sensitively modulate intrachain charge transport. However, simple, generic nonsynthetic approaches for tuning backbone planarity and the ensuing multiscale assembly process do not exist. We first demonstrate that printing flow is capable of planarizing the originally twisted polymer backbone to substantially increase the conjugation length. This conformation change leads to a marked morphological transition from chiral, twinned domains to achiral, highly aligned morphology, hence a fourfold increase in charge carrier mobilities. We found a surprising mechanism that flow extinguishes a lyotropic twist-bend mesophase upon backbone planarization, leading to the observed morphology and electronic structure transitions.

View Accepted Manuscript (DOE)

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

Sponsoring Organization:: American Association of University Women (AAUW); European Union’s Horizon 2020; National Science Foundation (NSF); US Department of the Navy, Office of Naval Research (ONR); USDOE Office of Science (SC)

Grant/Contract Number:: AC02-06CH11357

OSTI ID:: 1600813

Journal Information:: Science Advances, Journal Name: Science Advances Journal Issue: 8 Vol. 5; ISSN 2375-2548

Publisher:: AAASCopyright Statement

Country of Publication:: United States

Language:: ENGLISH

References (56)

High-Performance Ambipolar Diketopyrrolopyrrole-Thieno[3,2- b ]thiophene Copolymer Field-Effect Transistors with Balanced Hole and Electron Mobilities Chen, Zhuoying; Lee, Mi Jung; Shahid Ashraf, Raja Advanced Materials, Vol. 24, Issue 5 https://doi.org/10.1002/adma.201102786	journal	October 2011
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
Charge-Transport Anisotropy in a Uniaxially Aligned Diketopyrrolopyrrole-Based Copolymer Schott, Sam; Gann, Eliot; Thomsen, Lars Advanced Materials, Vol. 27, Issue 45 https://doi.org/10.1002/adma.201502437	journal	October 2015
Organic and Polymeric Semiconductors Enhanced by Noncovalent Conformational Locks Huang, Hui; Yang, Lei; Facchetti, Antonio Chemical Reviews, Vol. 117, Issue 15 https://doi.org/10.1021/acs.chemrev.7b00084	journal	July 2017
Naphthodithiophene-Based Conjugated Polymer with Linear, Planar Backbone Conformation and Strong Intermolecular Packing for Efficient Organic Solar Cells Lee, Jaewon; Ko, Hyomin; Song, Eunjoo ACS Applied Materials & Interfaces, Vol. 7, Issue 38 https://doi.org/10.1021/acsami.5b04884	journal	September 2015
Crystalline Ultrasmooth Self-Assembled Monolayers of Alkylsilanes for Organic Field-Effect Transistors Ito, Yutaka; Virkar, Ajay A.; Mannsfeld, Stefan Journal of the American Chemical Society, Vol. 131, Issue 26 https://doi.org/10.1021/ja9029957	journal	July 2009
Drying of a Solution in a Meniscus: A Model Coupling the Liquid and the Gas Phases Doumenc, F.; Guerrier, B. Langmuir, Vol. 26, Issue 17 https://doi.org/10.1021/la1018373	journal	September 2010
From Convective Assembly to Landau−Levich Deposition of Multilayered Phospholipid Films of Controlled Thickness Le Berre, Maël; Chen, Yong; Baigl, Damien Langmuir, Vol. 25, Issue 5 https://doi.org/10.1021/la803646e	journal	March 2009
Tuning charge transport in solution-sheared organic semiconductors using lattice strain Giri, Gaurav; Verploegen, Eric; Mannsfeld, Stefan C. B. Nature, Vol. 480, Issue 7378, p. 504-508 https://doi.org/10.1038/nature10683	journal	December 2011
Approaching disorder-free transport in high-mobility conjugated polymers Venkateshvaran, Deepak; Nikolka, Mark; Sadhanala, Aditya Nature, Vol. 515, Issue 7527 https://doi.org/10.1038/nature13854	journal	November 2014
Dynamic-template-directed multiscale assembly for large-area coating of highly-aligned conjugated polymer thin films Mohammadi, Erfan; Zhao, Chuankai; Meng, Yifei Nature Communications, Vol. 8, Issue 1 https://doi.org/10.1038/ncomms16070	journal	July 2017
A general relationship between disorder, aggregation and charge transport in conjugated polymers Noriega, Rodrigo; Rivnay, Jonathan; Vandewal, Koen Nature Materials, Vol. 12, Issue 11 https://doi.org/10.1038/nmat3722	journal	August 2013
Flow induced crystallisation of polymers Lamberti, Gaetano Chem. Soc. Rev., Vol. 43, Issue 7 https://doi.org/10.1039/c3cs60308c	journal	January 2014
Enabling high-mobility, ambipolar charge-transport in a DPP-benzotriazole copolymer by side-chain engineering Gruber, Mathias; Jung, Seok-Heon; Schott, Sam Chemical Science, Vol. 6, Issue 12 https://doi.org/10.1039/c5sc01326g	journal	January 2015
Chiral heliconical ground state of nanoscale pitch in a nematic liquid crystal of achiral molecular dimers Chen, D.; Porada, J. H.; Hooper, J. B. Proceedings of the National Academy of Sciences, Vol. 110, Issue 40, p. 15931-15936 https://doi.org/10.1073/pnas.1314654110	journal	September 2013
Multistep hierarchical self-assembly of chiral nanopore arrays Kim, Hanim; Lee, Sunhee; Shin, Tae Joo Proceedings of the National Academy of Sciences, Vol. 111, Issue 40 https://doi.org/10.1073/pnas.1414840111	journal	September 2014
Aggregation control in natural brush-printed conjugated polymer films and implications for enhancing charge transport Wang, Gang; Huang, Wei; Eastham, Nicholas D. Proceedings of the National Academy of Sciences, Vol. 114, Issue 47 https://doi.org/10.1073/pnas.1713634114	journal	November 2017
Optical Spectroscopy of a Polyfluorene Copolymer at High Pressure: Intra- and Intermolecular Interactions Schmidtke, Johanna P.; Kim, Ji-Seon; Gierschner, Johannes Physical Review Letters, Vol. 99, Issue 16 https://doi.org/10.1103/physrevlett.99.167401	journal	October 2007
Phase behaviors of colloidal analogs of bent-core liquid crystals Yang, Yang; Pei, Hanwen; Chen, Guangdong Science Advances, Vol. 4, Issue 5 https://doi.org/10.1126/sciadv.aas8829	journal	May 2018
On the spontaneous symmetry breaking in the mesophases of achiral banana-shaped molecules Dozov, I. Europhysics Letters (EPL), Vol. 56, Issue 2 https://doi.org/10.1209/epl/i2001-00513-x	journal	October 2001
Directly Drawn Organic Transistors by Capillary Pen: A New Facile Patterning Method using Capillary Action for Soluble Organic Materials Kang, Boseok; Min, Honggi; Seo, Unsuk Advanced Materials, Vol. 25, Issue 30 https://doi.org/10.1002/adma.201300006	journal	May 2013
Locking the Coplanar Conformation of π-Conjugated Molecules and Macromolecules Using Dynamic Noncovalent Bonds Zhu, Congzhi; Fang, Lei Macromolecular Rapid Communications, Vol. 39, Issue 2 https://doi.org/10.1002/marc.201700241	journal	June 2017
Hydrodynamically induced crystallization of polymers from solution: III. Morphology Pennings, A. J.; Mark, J. M. A. A.; Kiel, A. M. Kolloid-Zeitschrift & Zeitschrift für Polymere, Vol. 237, Issue 2 https://doi.org/10.1007/BF02086847	journal	April 1970
Hydrodynamically induced crystallization of polymers from solution: VII.: On the origin of persistent lamellar overgrowth of Shish-kebab fibers Pennings, A. J.; Lageveen, R.; de Vries, R. S. Colloid and Polymer Science, Vol. 255, Issue 6 https://doi.org/10.1007/bf01549739	journal	June 1977
Hydrodynamically induced crystallization of polymers from solution: II. The effect of secondary flow Pennings, A. J.; Mark, J. M. A. A.; Booij, H. C. Kolloid-Zeitschrift & Zeitschrift für Polymere, Vol. 236, Issue 2 https://doi.org/10.1007/bf02086621	journal	February 1970
Flow-Directed Crystallization for Printed Electronics Qu, Ge; Kwok, Justin J.; Diao, Ying Accounts of Chemical Research, Vol. 49, Issue 12 https://doi.org/10.1021/acs.accounts.6b00445	journal	November 2016
Characterizing the Polymer:Fullerene Intermolecular Interactions Sweetnam, Sean; Vandewal, Koen; Cho, Eunkyung Chemistry of Materials, Vol. 28, Issue 5 https://doi.org/10.1021/acs.chemmater.5b03378	journal	February 2016
Automated Analysis of Orientational Order in Images of Fibrillar Materials Persson, Nils E.; McBride, Michael A.; Grover, Martha A. Chemistry of Materials, Vol. 29, Issue 1 https://doi.org/10.1021/acs.chemmater.6b01825	journal	September 2016
Flow-Induced Crystallization of Polymers: Molecular and Thermodynamic Considerations Wang, Zhen; Ma, Zhe; Li, Liangbin Macromolecules, Vol. 49, Issue 5 https://doi.org/10.1021/acs.macromol.5b02688	journal	February 2016
π-Conjugated Polymers for Organic Electronics and Photovoltaic Cell Applications ^† Facchetti, Antonio Chemistry of Materials, Vol. 23, Issue 3 https://doi.org/10.1021/cm102419z	journal	February 2011
Control of Polymer-Packing Orientation in Thin Films through Synthetic Tailoring of Backbone Coplanarity Chen, Mark S.; Niskala, Jeremy R.; Unruh, David A. Chemistry of Materials, Vol. 25, Issue 20 https://doi.org/10.1021/cm402489a	journal	October 2013
The Effect of Chain Bending on the Photophysical Properties of Conjugated Polymers Hestand, Nicholas J.; Spano, Frank C. The Journal of Physical Chemistry B, Vol. 118, Issue 28 https://doi.org/10.1021/jp501857n	journal	April 2014
Enhancement of Out-of-plane Mobility in P3HT Film by Rubbing: Aggregation and Planarity Enhanced with Low Regioregularity Kajiya, Daisuke; Ozawa, Shuhei; Koganezawa, Tomoyuki The Journal of Physical Chemistry C, Vol. 119, Issue 15 https://doi.org/10.1021/jp510675r	journal	April 2015
Determination of Solvent–Polymer and Polymer–Polymer Flory–Huggins Interaction Parameters for Poly(3-hexylthiophene) via Solvent Vapor Swelling Emerson, Jillian A.; Toolan, Daniel T. W.; Howse, Jonathan R. Macromolecules, Vol. 46, Issue 16 https://doi.org/10.1021/ma400597j	journal	August 2013
Biomimetic self-templating supramolecular structures Chung, Woo-Jae; Oh, Jin-Woo; Kwak, Kyungwon Nature, Vol. 478, Issue 7369 https://doi.org/10.1038/nature10513	journal	October 2011
Molecular origin of high field-effect mobility in an indacenodithiophene–benzothiadiazole copolymer Zhang, Xinran; Bronstein, Hugo; Kronemeijer, Auke J. Nature Communications, Vol. 4, Issue 1 https://doi.org/10.1038/ncomms3238	journal	July 2013
Flow-enhanced solution printing of all-polymer solar cells Diao, Ying; Zhou, Yan; Kurosawa, Tadanori Nature Communications, Vol. 6, Issue 1 https://doi.org/10.1038/ncomms8955	journal	August 2015
Solution coating of large-area organic semiconductor thin films with aligned single-crystalline domains Diao, Ying; Tee, Benjamin C-K.; Giri, Gaurav Nature Materials, Vol. 12, Issue 7 https://doi.org/10.1038/nmat3650	journal	June 2013
Exploring the origin of high optical absorption in conjugated polymers Vezie, Michelle S.; Few, Sheridan; Meager, Iain Nature Materials, Vol. 15, Issue 7 https://doi.org/10.1038/nmat4645	journal	May 2016
Critical assessment of charge mobility extraction in FETs Choi, Hyun Ho; Cho, Kilwon; Frisbie, C. Daniel Nature Materials, Vol. 17, Issue 1 https://doi.org/10.1038/nmat5035	journal	December 2017
Flow induced crystallisation of polymers Lamberti, Gaetano Chem. Soc. Rev., Vol. 43, Issue 7 https://doi.org/10.1039/C3CS60308C	journal	January 2014
Probing the interfacial molecular packing in TIPS-pentacene organic semiconductors by surface enhanced Raman scattering Xu, Jie; Diao, Ying; Zhou, Dongshan J. Mater. Chem. C, Vol. 2, Issue 16 https://doi.org/10.1039/C3TC32581D	journal	January 2014
Enabling high-mobility, ambipolar charge-transport in a DPP-benzotriazole copolymer by side-chain engineering Gruber, Mathias; Jung, Seok-Heon; Schott, Sam Chemical Science, Vol. 6, Issue 12 https://doi.org/10.1039/C5SC01326G	journal	January 2015
Progression from nano to macro science in soft matter systems: dimers to trimers and oligomers in twist-bend liquid crystals Mandle, Richard J.; Goodby, John W. RSC Advances, Vol. 6, Issue 41 https://doi.org/10.1039/C6RA03594A	journal	January 2016
Understanding the twist-bend nematic phase: the characterisation of 1-(4-cyanobiphenyl-4′-yloxy)-6-(4-cyanobiphenyl-4′-yl)hexane (CB6OCB) and comparison with CB7CB Paterson, Daniel A.; Gao, Min; Kim, Young-Ki Soft Matter, Vol. 12, Issue 32 https://doi.org/10.1039/C6SM00537C	journal	January 2016
Systematic control of heteroatoms in donor–acceptor copolymers and its effects on molecular conformation and photovoltaic performance Wood, Sebastian; Kim, Ji-Hoon; Wade, Jessica Journal of Materials Chemistry C, Vol. 4, Issue 34 https://doi.org/10.1039/C6TC01936F	journal	January 2016
Synthesis and properties of small band gap thienoisoindigo based conjugated polymers Van Pruissen, Gijs W. P.; Gholamrezaie, Fatemeh; Wienk, Martijn M. Journal of Materials Chemistry, Vol. 22, Issue 38 https://doi.org/10.1039/c2jm34668k	journal	January 2012
High-performance organic thin-film transistors with metal oxide/metal bilayer electrode Chu, Chih-Wei; Li, Sheng-Han; Chen, Chieh-Wei Applied Physics Letters, Vol. 87, Issue 19, Article No. 193508 https://doi.org/10.1063/1.2126140	journal	November 2005
Comparison of theories for the translational and rotational diffusion coefficients of rod‐like macromolecules. Application to short DNA fragments Tirado, M. Mercedes; Martínez, Carmen López; de la Torre, José García The Journal of Chemical Physics, Vol. 81, Issue 4 https://doi.org/10.1063/1.447827	journal	August 1984
Theory of optical transitions in conjugated polymers. II. Real systems Marcus, Max; Tozer, Oliver Robert; Barford, William The Journal of Chemical Physics, Vol. 141, Issue 16 https://doi.org/10.1063/1.4897985	journal	October 2014
Optical Spectroscopy of a Polyfluorene Copolymer at High Pressure: Intra- and Intermolecular Interactions Schmidtke, Johanna P.; Kim, Ji-Seon; Gierschner, Johannes Physical Review Letters, Vol. 99, Issue 16 https://doi.org/10.1103/PhysRevLett.99.167401	journal	October 2007
GIXSGUI : a MATLAB toolbox for grazing-incidence X-ray scattering data visualization and reduction, and indexing of buried three-dimensional periodic nanostructured films Jiang, Zhang Journal of Applied Crystallography, Vol. 48, Issue 3 https://doi.org/10.1107/S1600576715004434	journal	April 2015
Vibrational Circular Dichroism in General Anisotropic Thin Solid Films: Measurement and Theoretical Approach Buffeteau, Thierry; Lagugné-Labarthet, François; Sourisseau, Claude Applied Spectroscopy, Vol. 59, Issue 6 https://doi.org/10.1366/0003702054280568	journal	June 2005
Progression from Nano to Macro Science in Soft Matter Systems: Dimers to Trimers and Oligomers in Twist-Bend Liquid Crystals Mandle, Richard; Goodby, John William University of York https://doi.org/10.15124/df2e26ef-1c9e-4cd5-980e-8a5f66a81621	dataset	January 2016
Exploring the origin of high optical absorption in conjugated polymers. Vezie, Michelle S.; Few, Sheridan; Meager, Iain Apollo - University of Cambridge Repository https://doi.org/10.17863/cam.20276	text	January 2016
Structure and Morphology Control in Thin Films of Conjugated Polymers for an Improved Charge Transport Wang, Haiyang; Xu, Yaozhuo; Yu, Xinhong Polymers, Vol. 5, Issue 4 https://doi.org/10.3390/polym5041272	journal	November 2013

Cited By (1)

Printing 2D Conjugated Polymer Monolayers and Their Distinct Electronic Properties Kafle, Prapti; Zhang, Fengjiao; Schorr, Noah B. Advanced Functional Materials, Vol. 30, Issue 12 https://doi.org/10.1002/adfm.201909787	journal	February 2020

Similar Records

Subtle Molecular Changes Largely Modulate Chiral Helical Assemblies of Achiral Conjugated Polymers by Tuning Solution-State Aggregation

Journal Article · Sun Nov 12 19:00:00 EST 2023 · ACS Central Science · OSTI ID:2470096

Tuning polymer-backbone coplanarity and conformational order to achieve high-performance printed all-polymer solar cells

Journal Article · Fri Mar 08 19:00:00 EST 2024 · Nature Communications · OSTI ID:2322453

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Tuning conformation, assembly, and charge transport properties of conjugated polymers by printing flow

Citation Formats

References (56)

Cited By (1)

Similar Records

Related Subjects