The Critical Role of Electron–Donating Thiophene Groups on the Mechanical and Thermal Properties of Donor–Acceptor Semiconducting Polymers
Abstract
Here, thin-film mechanical properties are investigated for diketopyrrolopyrrole (DPP)-based conjugated polymers with varying num- bers of isolated thiophene moieties and sizes of fused thiophene rings in the polymer backbone. Interestingly, it is found that these thiophene units act as an antiplasticizer, where more isolated thiophene rings or bigger fused rings result in an increased glass transition temperature (Tg) of the polymer backbone, and consequently elastic modulus of the respective DPP polymers. Detailed
- Authors:
-
[1]
- University of Southern Mississippi, Hattiesburg, MS (United States)
- University of Windsor, Ontario (Canada)
- Nanjing University (China)
- National Taiwan University of Science and Technology, Taipei (Taiwan)
- Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)
- Publication Date:
- Research Org.:
- University of Southern Mississippi, Hattiesburg, MS (United States); Univ. of Southern Mississippi, Hattiesburg, MS (United States); Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC), Basic Energy Sciences (BES); Natural Sciences and Engineering Research Council of Canada (NSERC); USDOE Office of Science (SC), Basic Energy Sciences (BES). Materials Sciences & Engineering Division
- OSTI Identifier:
- 1985339
- Alternate Identifier(s):
- OSTI ID: 1499211; OSTI ID: 1599395; OSTI ID: 1599798; OSTI ID: 1774743
- Grant/Contract Number:
- SC0019361; AC02‐76SF00515; AC02‐05CH11231; AC02-05CH11231; RGPIN-2017-06611; AC02-76SF00515
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Advanced Electronic Materials
- Additional Journal Information:
- Journal Volume: 5; Journal Issue: 5; Journal ID: ISSN 2199-160X
- Publisher:
- Wiley
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 36 MATERIALS SCIENCE; conjugated polymers; conjugation linkers; stretchable electronics; structure-property relationship; thermomechanical properties
Citation Formats
Zhang, Song, Ocheje, Michael U., Huang, Lifeng, Galuska, Luke, Cao, Zhiqiang, Luo, Shaochuan, Cheng, Yu‐Hsuan, Ehlenberg, Dakota, Goodman, Renée B., Zhou, Dongshan, Liu, Yi, Chiu, Yu‐Cheng, Azoulay, Jason D., Rondeau‐Gagné, Simon, and Gu, Xiaodan. The Critical Role of Electron–Donating Thiophene Groups on the Mechanical and Thermal Properties of Donor–Acceptor Semiconducting Polymers. United States: N. p., 2019.
Web. doi:10.1002/aelm.201800899.
Zhang, Song, Ocheje, Michael U., Huang, Lifeng, Galuska, Luke, Cao, Zhiqiang, Luo, Shaochuan, Cheng, Yu‐Hsuan, Ehlenberg, Dakota, Goodman, Renée B., Zhou, Dongshan, Liu, Yi, Chiu, Yu‐Cheng, Azoulay, Jason D., Rondeau‐Gagné, Simon, & Gu, Xiaodan. The Critical Role of Electron–Donating Thiophene Groups on the Mechanical and Thermal Properties of Donor–Acceptor Semiconducting Polymers. United States. https://doi.org/10.1002/aelm.201800899
Zhang, Song, Ocheje, Michael U., Huang, Lifeng, Galuska, Luke, Cao, Zhiqiang, Luo, Shaochuan, Cheng, Yu‐Hsuan, Ehlenberg, Dakota, Goodman, Renée B., Zhou, Dongshan, Liu, Yi, Chiu, Yu‐Cheng, Azoulay, Jason D., Rondeau‐Gagné, Simon, and Gu, Xiaodan. Wed .
"The Critical Role of Electron–Donating Thiophene Groups on the Mechanical and Thermal Properties of Donor–Acceptor Semiconducting Polymers". United States. https://doi.org/10.1002/aelm.201800899. https://www.osti.gov/servlets/purl/1985339.
@article{osti_1985339,
title = {The Critical Role of Electron–Donating Thiophene Groups on the Mechanical and Thermal Properties of Donor–Acceptor Semiconducting Polymers},
author = {Zhang, Song and Ocheje, Michael U. and Huang, Lifeng and Galuska, Luke and Cao, Zhiqiang and Luo, Shaochuan and Cheng, Yu‐Hsuan and Ehlenberg, Dakota and Goodman, Renée B. and Zhou, Dongshan and Liu, Yi and Chiu, Yu‐Cheng and Azoulay, Jason D. and Rondeau‐Gagné, Simon and Gu, Xiaodan},
abstractNote = {Here, thin-film mechanical properties are investigated for diketopyrrolopyrrole (DPP)-based conjugated polymers with varying num- bers of isolated thiophene moieties and sizes of fused thiophene rings in the polymer backbone. Interestingly, it is found that these thiophene units act as an antiplasticizer, where more isolated thiophene rings or bigger fused rings result in an increased glass transition temperature (Tg) of the polymer backbone, and consequently elastic modulus of the respective DPP polymers. Detailed},
doi = {10.1002/aelm.201800899},
journal = {Advanced Electronic Materials},
number = 5,
volume = 5,
place = {United States},
year = {Wed Mar 13 00:00:00 EDT 2019},
month = {Wed Mar 13 00:00:00 EDT 2019}
}
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Works referenced in this record:
25th Anniversary Article: Organic Field-Effect Transistors: The Path Beyond Amorphous Silicon
journal, January 2014
- Sirringhaus, Henning
- Advanced Materials, Vol. 26, Issue 9
Semiconducting π-Conjugated Systems in Field-Effect Transistors: A Material Odyssey of Organic Electronics
journal, November 2011
- Wang, Chengliang; Dong, Huanli; Hu, Wenping
- Chemical Reviews, Vol. 112, Issue 4
Organic single crystals: Addressing the fundamentals of organic electronics
journal, January 2013
- Podzorov, Vitaly
- MRS Bulletin, Vol. 38, Issue 1
25th Anniversary Article: Key Points for High-Mobility Organic Field-Effect Transistors
journal, September 2013
- Dong, Huanli; Fu, Xiaolong; Liu, Jie
- Advanced Materials, Vol. 25, Issue 43
Recent Progress in High-Mobility Organic Transistors: A Reality Check
journal, July 2018
- Paterson, Alexandra F.; Singh, Saumya; Fallon, Kealan J.
- Advanced Materials, Vol. 30, Issue 36
Recent Advances in Bulk Heterojunction Polymer Solar Cells
journal, August 2015
- Lu, Luyao; Zheng, Tianyue; Wu, Qinghe
- Chemical Reviews, Vol. 115, Issue 23
An indacenodithiophene-based semiconducting polymer with high ductility for stretchable organic electronics
journal, January 2017
- Li, Yilin; Tatum, Wesley K.; Onorato, Jonathan W.
- Polymer Chemistry, Vol. 8, Issue 34
Polymer solar cells
journal, February 2012
- Li, Gang; Zhu, Rui; Yang, Yang
- Nature Photonics, Vol. 6, Issue 3
Factors Limiting Device Efficiency in Organic Photovoltaics
journal, December 2012
- Janssen, René A. J.; Nelson, Jenny
- Advanced Materials, Vol. 25, Issue 13
25th Anniversary Article: Bulk Heterojunction Solar Cells: Understanding the Mechanism of Operation
journal, December 2013
- Heeger, Alan J.
- Advanced Materials, Vol. 26, Issue 1
Organic thermoelectric materials for energy harvesting and temperature control
journal, August 2016
- Russ, Boris; Glaudell, Anne; Urban, Jeffrey J.
- Nature Reviews Materials, Vol. 1, Issue 10
Donor–Acceptor Polymers
journal, July 2015
- Müllen, Klaus; Pisula, Wojciech
- Journal of the American Chemical Society, Vol. 137, Issue 30
Charge Transport in Organic Semiconductors
journal, April 2007
- Coropceanu, Veaceslav; Cornil, Jérôme; da Silva Filho, Demetrio A.
- Chemical Reviews, Vol. 107, Issue 4
Poly(3-hexylthiophene) (P3HT): fruit fly or outlier in organic solar cell research?
journal, January 2017
- Kleinschmidt, Andrew T.; Root, Samuel E.; Lipomi, Darren J.
- Journal of Materials Chemistry A, Vol. 5, Issue 23
Organic solar cells based on non-fullerene acceptors
journal, January 2018
- Hou, Jianhui; Inganäs, Olle; Friend, Richard H.
- Nature Materials, Vol. 17, Issue 2
Over 14% Efficiency in Polymer Solar Cells Enabled by a Chlorinated Polymer Donor
journal, March 2018
- Zhang, Shaoqing; Qin, Yunpeng; Zhu, Jie
- Advanced Materials, Vol. 30, Issue 20
Efficient non-fullerene organic solar cells employing sequentially deposited donor–acceptor layers
journal, January 2018
- Zhang, Jiangbin; Kan, Bin; Pearson, Andrew J.
- Journal of Materials Chemistry A, Vol. 6, Issue 37
Organic and solution-processed tandem solar cells with 17.3% efficiency
journal, August 2018
- Meng, Lingxian; Zhang, Yamin; Wan, Xiangjian
- Science, Vol. 361, Issue 6407
Best of Both Worlds: Conjugated Polymers Exhibiting Good Photovoltaic Behavior and High Tensile Elasticity
journal, March 2014
- Savagatrup, Suchol; Printz, Adam D.; Rodriquez, Daniel
- Macromolecules, Vol. 47, Issue 6
Stretchable electronics: recent progress in the preparation of stretchable and self-healing semiconducting conjugated polymers
journal, December 2017
- Ocheje, Michael U.; Charron, Brynn P.; Nyayachavadi, Audithya
- Flexible and Printed Electronics, Vol. 2, Issue 4
Stretchable Polymer Semiconductors for Plastic Electronics
journal, January 2018
- Wang, Ging-Ji Nathan; Gasperini, Andrea; Bao, Zhenan
- Advanced Electronic Materials, Vol. 4, Issue 2
Mechanical Properties of Organic Semiconductors for Stretchable, Highly Flexible, and Mechanically Robust Electronics
journal, March 2017
- Root, Samuel E.; Savagatrup, Suchol; Printz, Adam D.
- Chemical Reviews, Vol. 117, Issue 9
Pursuing prosthetic electronic skin
journal, July 2016
- Chortos, Alex; Liu, Jia; Bao, Zhenan
- Nature Materials, Vol. 15, Issue 9
The rise of plastic bioelectronics
journal, December 2016
- Someya, Takao; Bao, Zhenan; Malliaras, George G.
- Nature, Vol. 540, Issue 7633
Correlations between Mechanical and Electrical Properties of Polythiophenes
journal, November 2010
- O’Connor, Brendan; Chan, Edwin P.; Chan, Calvin
- ACS Nano, Vol. 4, Issue 12
Tough, Semiconducting Polyethylene-poly(3-hexylthiophene) Diblock Copolymers
journal, October 2007
- Müller, C.; Goffri, S.; Breiby, D. W.
- Advanced Functional Materials, Vol. 17, Issue 15
Photoinduced Anisotropic Assembly of Conjugated Polymers in Insulating Polymer Blends
journal, June 2015
- Chang, Mincheol; Choi, Dalsu; Wang, Gang
- ACS Applied Materials & Interfaces, Vol. 7, Issue 25
Elastomer–Polymer Semiconductor Blends for High-Performance Stretchable Charge Transport Networks
journal, February 2016
- Choi, Dalsu; Kim, Hyungchul; Persson, Nils
- Chemistry of Materials, Vol. 28, Issue 4
Advances in Charge Carrier Mobilities of Semiconducting Polymers Used in Organic Transistors
journal, September 2013
- Holliday, Sarah; Donaghey, Jenny E.; McCulloch, Iain
- Chemistry of Materials, Vol. 26, Issue 1
Record High Hole Mobility in Polymer Semiconductors via Side-Chain Engineering
journal, September 2013
- Kang, Il; Yun, Hui-Jun; Chung, Dae Sung
- Journal of the American Chemical Society, Vol. 135, Issue 40
Recent progress in the development of n-type organic semiconductors for organic field effect transistors
journal, January 2017
- Quinn, Jesse T. E.; Zhu, Jiaxin; Li, Xu
- Journal of Materials Chemistry C, Vol. 5, Issue 34
Recent Advances in the Development of Semiconducting DPP-Containing Polymers for Transistor Applications
journal, September 2012
- Nielsen, Christian B.; Turbiez, Mathieu; McCulloch, Iain
- Advanced Materials, Vol. 25, Issue 13
Highly stretchable polymer semiconductor films through the nanoconfinement effect
journal, January 2017
- Xu, Jie; Wang, Sihong; Wang, Ging-Ji Nathan
- Science, Vol. 355, Issue 6320
Stretchable, elastic materials and devices for solar energy conversion
journal, January 2011
- Lipomi, Darren J.; Bao, Zhenan
- Energy & Environmental Science, Vol. 4, Issue 9
A Rapid and Facile Soft Contact Lamination Method: Evaluation of Polymer Semiconductors for Stretchable Transistors
journal, July 2014
- Wu, Hung-Chin; Benight, Stephanie J.; Chortos, Alex
- Chemistry of Materials, Vol. 26, Issue 15
Conjugation-Break Spacers in Semiconducting Polymers: Impact on Polymer Processability and Charge Transport Properties
journal, March 2015
- Zhao, Yan; Zhao, Xikang; Zang, Yaping
- Macromolecules, Vol. 48, Issue 7
Diketopyrrolopyrrole-Based π-Conjugated Copolymer Containing β-Unsubstituted Quintetthiophene Unit: A Promising Material Exhibiting High Hole-Mobility for Organic Thin-Film Transistors
journal, November 2012
- Yi, Zhengran; Sun, Xiangnan; Zhao, Yan
- Chemistry of Materials, Vol. 24, Issue 22
Effect of methyl substitution on the diketopyrrolopyrrole-based semiconducting polymers for organic thin film transistors
journal, May 2018
- Kim, Hee Su; Song, Eunjoo; Lee, Seon Baek
- Organic Electronics, Vol. 56
Taming Charge Transport in Semiconducting Polymers with Branched Alkyl Side Chains
journal, July 2017
- Schroeder, Bob C.; Kurosawa, Tadanori; Fu, Tianren
- Advanced Functional Materials, Vol. 27, Issue 34
Mechanical Properties of a Library of Low-Band-Gap Polymers
journal, March 2016
- Roth, Bérenger; Savagatrup, Suchol; V. de los Santos, Nathaniel
- Chemistry of Materials, Vol. 28, Issue 7
Effect of Broken Conjugation on the Stretchability of Semiconducting Polymers
journal, August 2016
- Savagatrup, Suchol; Zhao, Xikang; Chan, Esther
- Macromolecular Rapid Communications, Vol. 37, Issue 19
Non-Conjugated Flexible Linkers in Semiconducting Polymers: A Pathway to Improved Processability without Compromising Device Performance
journal, May 2016
- Schroeder, Bob C.; Chiu, Yu-Cheng; Gu, Xiaodan
- Advanced Electronic Materials, Vol. 2, Issue 7
Effects of Molecular Structure and Packing Order on the Stretchability of Semicrystalline Conjugated Poly(Tetrathienoacene-diketopyrrolopyrrole) Polymers
journal, December 2016
- Lu, Chien; Lee, Wen-Ya; Gu, Xiaodan
- Advanced Electronic Materials, Vol. 3, Issue 2
Nonhalogenated Solvent Processable and Printable High-Performance Polymer Semiconductor Enabled by Isomeric Nonconjugated Flexible Linkers
journal, June 2018
- Wang, Ging-Ji Nathan; Molina-Lopez, Francisco; Zhang, Hongyi
- Macromolecules, Vol. 51, Issue 13
Inducing Elasticity through Oligo-Siloxane Crosslinks for Intrinsically Stretchable Semiconducting Polymers
journal, August 2016
- Wang, Ging-Ji Nathan; Shaw, Leo; Xu, Jie
- Advanced Functional Materials, Vol. 26, Issue 40
Intrinsically stretchable and healable semiconducting polymer for organic transistors
journal, November 2016
- Oh, Jin Young; Rondeau-Gagné, Simon; Chiu, Yu-Cheng
- Nature, Vol. 539, Issue 7629
Amide-Containing Alkyl Chains in Conjugated Polymers: Effect on Self-Assembly and Electronic Properties
journal, February 2018
- Ocheje, Michael U.; Charron, Brynn P.; Cheng, Yu-Hsuan
- Macromolecules, Vol. 51, Issue 4
Copolymers of diketopyrrolopyrrole and thienothiophene for photovoltaic cells
journal, January 2011
- Bijleveld, Johan C.; Verstrijden, R. A. Melanie; Wienk, Martijn M.
- Journal of Materials Chemistry, Vol. 21, Issue 25
2,5-Bis(2-octyldodecyl)pyrrolo[3,4- c ]pyrrole-1,4-(2 H ,5 H )-dione-Based Donor–Acceptor Alternating Copolymer Bearing 5,5′-Di(thiophen-2-yl)-2,2′-biselenophene Exhibiting 1.5 cm 2 ·V –1 ·s –1 Hole Mobility in Thin-Film Transistors
journal, July 2011
- Ha, Jae Seung; Kim, Kyung Hwan; Choi, Dong Hoon
- Journal of the American Chemical Society, Vol. 133, Issue 27, p. 10364-10367
High mobility diketopyrrolopyrrole (DPP)-based organic semiconductor materials for organic thin film transistors and photovoltaics
journal, January 2013
- Li, Yuning; Sonar, Prashant; Murphy, Leanne
- Energy & Environmental Science, Vol. 6, Issue 6
A high mobility conjugated polymer based on dithienothiophene and diketopyrrolopyrrole for organic photovoltaics
journal, January 2012
- Jung, Jae Woong; Liu, Feng; Russell, Thomas P.
- Energy & Environmental Science, Vol. 5, Issue 5
Probing the Viscoelastic Property of Pseudo Free-Standing Conjugated Polymeric Thin Films
journal, May 2018
- Zhang, Song; Ocheje, Michael U.; Luo, Shaochuan
- Macromolecular Rapid Communications, Vol. 39, Issue 14
A buckling-based metrology for measuring the elastic moduli of polymeric thin films
journal, July 2004
- Stafford, Christopher M.; Harrison, Christopher; Beers, Kathryn L.
- Nature Materials, Vol. 3, Issue 8, p. 545-550
Directly Measuring the Complete Stress–Strain Response of Ultrathin Polymer Films
journal, September 2015
- Liu, Yujie; Chen, Yu-Cheng; Hutchens, Shelby
- Macromolecules, Vol. 48, Issue 18
Chain Entanglement in Thin Freestanding Polymer Films
journal, April 2005
- Si, Lun; Massa, Michael V.; Dalnoki-Veress, Kari
- Physical Review Letters, Vol. 94, Issue 12
Polymer Chain Shape of Poly(3-alkylthiophenes) in Solution Using Small-Angle Neutron Scattering
journal, February 2013
- McCulloch, Bryan; Ho, Victor; Hoarfrost, Megan
- Macromolecules, Vol. 46, Issue 5
The impact of molecular weight on microstructure and charge transport in semicrystalline polymer semiconductors–poly(3-hexylthiophene), a model study
journal, December 2013
- Koch, Felix Peter Vinzenz; Rivnay, Jonathan; Foster, Sam
- Progress in Polymer Science, Vol. 38, Issue 12
Comparison of Methods for Determining the Mechanical Properties of Semiconducting Polymer Films for Stretchable Electronics
journal, March 2017
- Rodriquez, Daniel; Kim, Jae-Han; Root, Samuel E.
- ACS Applied Materials & Interfaces, Vol. 9, Issue 10
Role of Molecular Weight on the Mechanical Device Properties of Organic Polymer Solar Cells
journal, January 2014
- Bruner, Christopher; Dauskardt, Reinhold
- Macromolecules, Vol. 47, Issue 3
Symmetry Breaking in Side Chains Leading to Mixed Orientations and Improved Charge Transport in Isoindigo- alt -Bithiophene Based Polymer Thin Films
journal, July 2017
- Xue, Guobiao; Zhao, Xikang; Qu, Ge
- ACS Applied Materials & Interfaces, Vol. 9, Issue 30
Second‐Order Transition Temperatures and Related Properties of Polystyrene. I. Influence of Molecular Weight
journal, June 1950
- Fox, Thomas G.; Flory, Paul J.
- Journal of Applied Physics, Vol. 21, Issue 6
Glass Transition Temperature of Conjugated Polymers by Oscillatory Shear Rheometry
journal, June 2017
- Xie, Renxuan; Lee, Youngmin; Aplan, Melissa P.
- Macromolecules, Vol. 50, Issue 13
Molecular Packing of High-Mobility Diketo Pyrrolo-Pyrrole Polymer Semiconductors with Branched Alkyl Side Chains
journal, September 2011
- Zhang, Xinran; Richter, Lee J.; DeLongchamp, Dean M.
- Journal of the American Chemical Society, Vol. 133, Issue 38
Importance of Solubilizing Group and Backbone Planarity in Low Band Gap Polymers for High Performance Ambipolar field-effect Transistors
journal, March 2012
- Lee, Joong Suk; Son, Seon Kyoung; Song, Sanghoon
- Chemistry of Materials, Vol. 24, Issue 7
Unraveling the Main Chain and Side Chain Effects on Thin Film Morphology and Charge Transport in Quinoidal Conjugated Polymers
journal, June 2018
- Liu, Xuncheng; He, Bo; Garzón-Ruiz, Andrés
- Advanced Functional Materials, Vol. 28, Issue 31
Flow-enhanced solution printing of all-polymer solar cells
journal, August 2015
- Diao, Ying; Zhou, Yan; Kurosawa, Tadanori
- Nature Communications, Vol. 6, Issue 1
Quantitative Determination of Organic Semiconductor Microstructure from the Molecular to Device Scale
journal, June 2012
- Rivnay, Jonathan; Mannsfeld, Stefan C. B.; Miller, Chad E.
- Chemical Reviews, Vol. 112, Issue 10
Quantification of Thin Film Crystallographic Orientation Using X-ray Diffraction with an Area Detector
journal, June 2010
- Baker, Jessy L.; Jimison, Leslie H.; Mannsfeld, Stefan
- Langmuir, Vol. 26, Issue 11
Glass transition of small polystyrene spheres in aqueous suspensions
journal, October 2003
- Sasaki, Takashi; Shimizu, Atsushi; Mourey, Thomas H.
- The Journal of Chemical Physics, Vol. 119, Issue 16
Structure/properties of conjugated conductive polymers. 1. Neutral poly(3-alkythiophene)s
journal, November 1992
- Chen, Show An; Ni, Jui Ming
- Macromolecules, Vol. 25, Issue 23
Poly(diketopyrrolopyrrole−terthiophene) for Ambipolar Logic and Photovoltaics
journal, November 2009
- Bijleveld, Johan C.; Zoombelt, Arjan P.; Mathijssen, Simon G. J.
- Journal of the American Chemical Society, Vol. 131, Issue 46
Synthesis of low bandgap polymer based on 3,6-dithien-2-yl-2,5-dialkylpyrrolo[3,4-c]pyrrole-1,4-dione for photovoltaic applications
journal, April 2011
- Zhang, Guobing; Fu, Yingying; Xie, Zhiyuan
- Solar Energy Materials and Solar Cells, Vol. 95, Issue 4
Unravelling the Thermomechanical Properties of Bulk Heterojunction Blends in Polymer Solar Cells
journal, April 2017
- Sharma, Anirudh; Pan, Xun; Campbell, Jonathan A.
- Macromolecules, Vol. 50, Issue 8
Calorimetric Glass Transition of Poly(2,6-dimethyl-1,5-phenylene oxide) Thin Films
journal, October 2008
- Zhou, Dongshan; Huth, Heiko; Gao, Yun
- Macromolecules, Vol. 41, Issue 20
Works referencing / citing this record:
Photophysical and Optical Properties of Semiconducting Polymer Nanoparticles Prepared from Hyaluronic Acid and Polysorbate 80
journal, December 2019
- Langlois, Adam; Mason, Gage T.; Nguyen, Michael H. L.
- ACS Omega, Vol. 4, Issue 27