Design rules for dynamic-template-directed crystallization of conjugated polymers

Mohammadi, Erfan; Qu, Ge; Kafle, Prapti; Jung, Seok-Heon; Lee, Jin-Kyun; Diao, Ying

doi:10.1039/c9me00042a

Design rules for dynamic-template-directed crystallization of conjugated polymers

Journal Article · Thu May 09 00:00:00 EDT 2019 · Molecular Systems Design & Engineering

DOI:https://doi.org/10.1039/c9me00042a· OSTI ID:1600814

^[1]; Qu, Ge ^[1]; Kafle, Prapti ^[1]; Jung, Seok-Heon ^[2]; ^[2]; ^[1]

Univ. of Illinois at Urbana-Champaign, IL (United States)
Inha Univ., Incheon (South Korea)

The multiscale morphology and device performance of printed semiconducting polymers are highly sensitive to the substrate/ink interfacial properties during solution coating. There is an urgent need for general design rules correlating the substrate properties and conjugated polymer (CP) morphology, which do not yet exist. Dynamic surfaces are particularly promising for templating highly crystalline and highly aligned conjugated polymer thin films and have been shown in recent studies. In this work, we implement the dynamic-templating method using a series of liquid-infused nanoporous substrates as a tool to study the impact of template reconfigurability and chemistry on the multiscale morphology of conjugated polymer thin films, using a high performing donor–acceptor polymer (DPP-BTz) as a model compound. By quantifying the enthalpy of adsorption, we demonstrate that the strength of template–CP interactions directly measures the effectiveness of dynamic surfaces in promoting conjugated polymer crystallization and alignment. We further show that the enthalpy of interactions increases by enhancing the template dynamics and is sensitively modulated by template chemistry. Specifically, increasing the template–CP interactions leads to a larger domain size and higher degree of crystallinity in templated conjugated polymer thin films prepared by meniscus-guided solution coating. This observation validates our hypothesis that dynamic templates function by promoting the nucleation of conjugated polymers. We also demonstrate that such dynamic-template-dependent morphology is independent of coating speed. Notably, the enhanced morphological properties modulate the charge carrier mobility in field-effect transistors (FETs) over an order of magnitude reaching a hole mobility of 2.8 cm² V^–1 s^–1. This work is a significant step towards establishing general guidelines on how the substrate–ink interfacial properties influence morphology and performance of solution coated CP thin films.

View Accepted Manuscript (DOE)

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

Sponsoring Organization:: Jiangsu Industrial Technology Research Institute (JITRI); National Science Foundation (NSF); USDOE Office of Science (SC)

Grant/Contract Number:: AC02-06CH11357

OSTI ID:: 1600814

Alternate ID(s):: OSTI ID: 1515588

Journal Information:: Molecular Systems Design & Engineering, Journal Name: Molecular Systems Design & Engineering Journal Issue: 1 Vol. 5; ISSN 2058-9689

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: ENGLISH

References (57)

Isothermal titration calorimetry and differential scanning calorimetry as complementary tools to investigate the energetics of biomolecular recognition Jelesarov, Ilian; Bosshard, Hans Rudolf Journal of Molecular Recognition, Vol. 12, Issue 1 https://doi.org/10.1002/(SICI)1099-1352(199901/02)12:1<3::AID-JMR441>3.0.CO;2-6	journal	January 1999
Enhancement of Field-Effect Mobility Due to Surface-Mediated Molecular Ordering in Regioregular Polythiophene Thin Film Transistors Kim, D. H.; Park, Y. D.; Jang, Y. Advanced Functional Materials, Vol. 15, Issue 1 https://doi.org/10.1002/adfm.200400054	journal	January 2005
An Improved Optical Method for Determining the Order Parameter in Thin Oriented Molecular Films and Demonstration of a Highly Axial Dipole Moment for the Lowest Energy π–π* Optical Transition in Poly(9,9- dioctylfluorene-co-bithiophene) Gather, M. C.; Bradley, D. D. C. Advanced Functional Materials, Vol. 17, Issue 3 https://doi.org/10.1002/adfm.200600056	journal	February 2007
The Effect of Interfacial Roughness on the Thin Film Morphology and Charge Transport of High-Performance Polythiophenes Jung, Youngsuk; Kline, R. Joseph; Fischer, Daniel A. Advanced Functional Materials, Vol. 18, Issue 5 https://doi.org/10.1002/adfm.200701089	journal	March 2008
Solution-Processed Nanoporous Organic Semiconductor Thin Films: Toward Health and Environmental Monitoring of Volatile Markers Zhang, Fengjiao; Qu, Ge; Mohammadi, Erfan Advanced Functional Materials, Vol. 27, Issue 23 https://doi.org/10.1002/adfm.201701117	journal	May 2017
Highly Oriented Polymer Semiconductor Films Compressed at the Surface of Ionic Liquids for High-Performance Polymeric Organic Field-Effect Transistors Soeda, Junshi; Matsui, Hiroyuki; Okamoto, Toshihiro Advanced Materials, Vol. 26, Issue 37 https://doi.org/10.1002/adma.201401495	journal	August 2014
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
Uniaxial Alignment of Conjugated Polymer Films for High-Performance Organic Field-Effect Transistors Khim, Dongyoon; Luzio, Alessandro; Bonacchini, Giorgio Ernesto Advanced Materials, Vol. 30, Issue 20 https://doi.org/10.1002/adma.201705463	journal	March 2018
Binding of DNA Nucleobases and Nucleosides with Graphene Varghese, Neenu; Mogera, Umesha; Govindaraj, Achutharao ChemPhysChem, Vol. 10, Issue 1 https://doi.org/10.1002/cphc.200800459	journal	January 2009
Vertical confinement and interface effects on the microstructure and charge transport of P3HT thin films Jimison, Leslie H.; Himmelberger, Scott; Duong, Duc T. Journal of Polymer Science Part B: Polymer Physics, Vol. 51, Issue 7 https://doi.org/10.1002/polb.23265	journal	February 2013
Natural and artificial heterogeneous nucleation in polymer crystallization Binsbergen, F. L. Journal of Polymer Science: Polymer Symposia, Vol. 59, Issue 1 https://doi.org/10.1002/polc.5070590104	journal	January 1977
Enzyme Kinetics Determined Using Calorimetry: A General Assay for Enzyme Activity? Todd, Matthew J.; Gomez, Javier Analytical Biochemistry, Vol. 296, Issue 2 https://doi.org/10.1006/abio.2001.5218	journal	September 2001
Rapid measurement of binding constants and heats of binding using a new titration calorimeter Wiseman, Thomas; Williston, Samuel; Brandts, John F. Analytical Biochemistry, Vol. 179, Issue 1 https://doi.org/10.1016/0003-2697(89)90213-3	journal	May 1989
Epitaxial crystallization of polymers on organic and polymeric substrates Wittmann, J. C.; Lotz, B. Progress in Polymer Science, Vol. 15, Issue 6 https://doi.org/10.1016/0079-6700(90)90025-V	journal	January 1990
Time-resolved fluorescence depolarization studies of rotational relaxation in viscous media Rice, Stephen A.; Kenney-Wallace, G. A. Chemical Physics, Vol. 47, Issue 2 https://doi.org/10.1016/0301-0104(80)85003-8	journal	April 1980
Contact angle measurement and contact angle interpretation Kwok, D. Y.; Neumann, A. W. Advances in Colloid and Interface Science, Vol. 81, Issue 3 https://doi.org/10.1016/S0001-8686(98)00087-6	journal	September 1999
Direct measurement of protein binding energetics by isothermal titration calorimetry Leavitt, Stephanie; Freire, Ernesto Current Opinion in Structural Biology, Vol. 11, Issue 5 https://doi.org/10.1016/S0959-440X(00)00248-7	journal	September 2001
Solvent driven performance in thin floating-films of PBTTT for organic field effect transistor: Role of macroscopic orientation Pandey, Manish; Pandey, Shyam S.; Nagamatsu, Shuichi Organic Electronics, Vol. 43 https://doi.org/10.1016/j.orgel.2017.01.031	journal	April 2017
Non-fullerene polymer acceptors based on perylene diimides in all-polymer solar cells Liu, Zhitian; Zeng, Di; Gao, Xiang Solar Energy Materials and Solar Cells, Vol. 189 https://doi.org/10.1016/j.solmat.2018.09.024	journal	January 2019
Solution Processable, Electrochromic Ion Gels for Sub-1 V, Flexible Displays on Plastic Moon, Hong Chul; Lodge, Timothy P.; Frisbie, C. Daniel Chemistry of Materials, Vol. 27, Issue 4 https://doi.org/10.1021/acs.chemmater.5b00026	journal	February 2015
Critical Role of Surface Energy in Guiding Crystallization of Solution-Coated Conjugated Polymer Thin Films Zhang, Fengjiao; Mohammadi, Erfan; Luo, Xuyi Langmuir, Vol. 34, Issue 3 https://doi.org/10.1021/acs.langmuir.7b02807	journal	October 2017
Understanding Interfacial Alignment in Solution Coated Conjugated Polymer Thin Films Qu, Ge; Zhao, Xikang; Newbloom, Gregory M. ACS Applied Materials & Interfaces, Vol. 9, Issue 33 https://doi.org/10.1021/acsami.7b08133	journal	August 2017
Conjugated Polymer-Based Chemical Sensors McQuade, D. Tyler; Pullen, Anthony E.; Swager, Timothy M. Chemical Reviews, Vol. 100, Issue 7 https://doi.org/10.1021/cr9801014	journal	July 2000
Viscosity of Glycerol and Its Aqueous Solutions Segur, J. B.; Oberstar, Helen E. Industrial & Engineering Chemistry, Vol. 43, Issue 9 https://doi.org/10.1021/ie50501a040	journal	September 1951
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
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
Dynamics of Solvation of the Fluorescent State of Some Electron Donor−Acceptor Molecules in Room Temperature Ionic Liquids, [BMIM][(CF ₃ SO ₂ ) ₂ N] and [EMIM][(CF ₃ SO ₂ ) ₂ N] Karmakar, Rana; Samanta, Anunay The Journal of Physical Chemistry A, Vol. 107, Issue 38 https://doi.org/10.1021/jp030683f	journal	September 2003
To Probe the Interaction of Methanol and Acetonitrile with the Ionic Liquid N , N , N -Trimethyl- N -propyl Ammonium Bis(trifluoromethanesulfonyl) Imide at Different Temperatures by Solvation Dynamics Study Pramanik, Rajib; Rao, Vishal Govind; Sarkar, Souravi The Journal of Physical Chemistry B, Vol. 113, Issue 25 https://doi.org/10.1021/jp900627h	journal	June 2009
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
Quantification of Thin Film Crystallographic Orientation Using X-ray Diffraction with an Area Detector Baker, Jessy L.; Jimison, Leslie H.; Mannsfeld, Stefan Langmuir, Vol. 26, Issue 11 https://doi.org/10.1021/la904840q	journal	June 2010
Systematic Investigation of the Thermodynamics of HSA Adsorption to N-iso-Propylacrylamide/N-tert-Butylacrylamide Copolymer Nanoparticles. Effects of Particle Size and Hydrophobicity Lindman, Stina; Lynch, Iseult; Thulin, Eva Nano Letters, Vol. 7, Issue 4 https://doi.org/10.1021/nl062743+	journal	March 2007
High Mobility Field Effect Transistors Based on Macroscopically Oriented Regioregular Copolymers Tseng, Hsin-Rong; Ying, Lei; Hsu, Ben B. Y. Nano Letters, Vol. 12, Issue 12 https://doi.org/10.1021/nl303612z	journal	February 2012
Charge separation in localized and delocalized electronic states in polymeric semiconductors Köhler, A.; dos Santos, D. A.; Beljonne, D. Nature, Vol. 392, Issue 6679 https://doi.org/10.1038/31901	journal	April 1998
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
Ultrafast formation of air-processable and high-quality polymer films on an aqueous substrate Noh, Jonghyeon; Jeong, Seonju; Lee, Jung-Yong Nature Communications, Vol. 7, Issue 1 https://doi.org/10.1038/ncomms12374	journal	August 2016
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
Highly oriented crystals at the buried interface in polythiophene thin-film transistors Joseph Kline, R.; McGehee, Michael D.; Toney, Michael F. Nature Materials, Vol. 5, Issue 3 https://doi.org/10.1038/nmat1590	journal	February 2006
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
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
NIH Image to ImageJ: 25 years of image analysis Schneider, Caroline A.; Rasband, Wayne S.; Eliceiri, Kevin W. Nature Methods, Vol. 9, Issue 7 https://doi.org/10.1038/nmeth.2089	journal	June 2012
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
Non-fullerene small molecule acceptors based on perylene diimides Liu, Zhitian; Wu, Yao; Zhang, Qi Journal of Materials Chemistry A, Vol. 4, Issue 45 https://doi.org/10.1039/C6TA06978A	journal	January 2016
Interfacial effects on solution-sheared thin-film transistors Guo, Dong-Yue; Tsai, Yi-bei; Yu, Ting-Feng Journal of Materials Chemistry C, Vol. 6, Issue 44 https://doi.org/10.1039/C8TC01439F	journal	January 2018
Recent progress in printable organic field effect transistors Tang, Wei; Huang, Yukun; Han, Lei Journal of Materials Chemistry C, Vol. 7, Issue 4 https://doi.org/10.1039/C8TC05485A	journal	January 2019
Control of mesoscale and nanoscale ordering of organic semiconductors at the gate dielectric/semiconductor interface for organic transistors Lee, Wi Hyoung; Cho, Jeong Ho; Cho, Kilwon Journal of Materials Chemistry, Vol. 20, Issue 13 https://doi.org/10.1039/b924415h	journal	January 2010
Graphene surface induced specific self-assembly of poly(3-hexylthiophene) for nanohybrid optoelectronics: from first-principles calculation to experimental characterizations Kim, Do Hwan; Lee, Hyo Sug; Shin, Hyeon-Jin Soft Matter, Vol. 9, Issue 22 https://doi.org/10.1039/c3sm27767d	journal	January 2013
Ultrafast dynamics of pyrrolidinium cation ionic liquids Shirota, Hideaki; Funston, Alison M.; Wishart, James F. The Journal of Chemical Physics, Vol. 122, Issue 18 https://doi.org/10.1063/1.1893797	journal	May 2005
Effects of the surface roughness of plastic-compatible inorganic dielectrics on polymeric thin film transistors Chabinyc, Michael L.; Lujan, Rene; Endicott, Fred Applied Physics Letters, Vol. 90, Issue 23 https://doi.org/10.1063/1.2746955	journal	June 2007
Anisotropic charge transport in highly oriented films of semiconducting polymer prepared by ribbon-shaped floating film Tripathi, Atul S. M.; Pandey, Manish; Sadakata, Shifumi Applied Physics Letters, Vol. 112, Issue 12 https://doi.org/10.1063/1.5000566	journal	March 2018
Multiscale assembly of solution-processed organic electronics: the critical roles of confinement, fluid flow, and interfaces Patel, Bijal B.; Diao, Ying Nanotechnology, Vol. 29, Issue 4 https://doi.org/10.1088/1361-6528/aa9d7c	journal	December 2017
III. An essay on the cohesion of fluids Young, Thomas Philosophical Transactions of the Royal Society of London, Vol. 95, p. 65-87 https://doi.org/10.1098/rstl.1805.0005	journal	January 1805
Optical constants of highly stretch-oriented poly( p -phenylene-vinylene): A joint experimental and theoretical study Comoretto, D.; Dellepiane, G.; Marabelli, F. Physical Review B, Vol. 62, Issue 15 https://doi.org/10.1103/PhysRevB.62.10173	journal	October 2000
The dedicated high-resolution grazing-incidence X-ray scattering beamline 8-ID-E at the Advanced Photon Source Jiang, Zhang; Li, Xuefa; Strzalka, Joseph Journal of Synchrotron Radiation, Vol. 19, Issue 4 https://doi.org/10.1107/S0909049512022017	journal	June 2012
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
Polymer Gate Dielectric Surface Viscoelasticity Modulates Pentacene Transistor Performance Kim, C.; Facchetti, A.; Marks, T. J. Science, Vol. 318, Issue 5847 https://doi.org/10.1126/science.1146458	journal	October 2007
Engineering semiconducting polymers for efficient charge transport Himmelberger, Scott; Salleo, Alberto MRS Communications, Vol. 5, Issue 3 https://doi.org/10.1557/mrc.2015.44	journal	June 2015
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

Cited By (1)

Recent advances in the orientation of conjugated polymers for organic field-effect transistors Pandey, Manish; Kumari, Nikita; Nagamatsu, Shuichi Journal of Materials Chemistry C, Vol. 7, Issue 43 https://doi.org/10.1039/c9tc04397g	journal	January 2019

Similar Records

Achieving High Alignment of Conjugated Polymers by Controlled Dip-Coating

Journal Article · Sun Apr 12 20:00:00 EDT 2020 · Advanced Electronic Materials · OSTI ID:1659423

Related Subjects

42 ENGINEERING

Design rules for dynamic-template-directed crystallization of conjugated polymers

Citation Formats

References (57)

Cited By (1)

Similar Records

Related Subjects