Enhancing the Solubility of Semiconducting Polymers in Eco-Friendly Solvents with Carbohydrate-Containing Side Chains

Mooney, Madison; Wang, Yunfei; Nyayachavadi, Audithya; Zhang, Song; Gu, Xiaodan; Rondeau-Gagné, Simon

doi:10.1021/acsami.1c02860

Enhancing the Solubility of Semiconducting Polymers in Eco-Friendly Solvents with Carbohydrate-Containing Side Chains

Journal Article · Wed May 19 00:00:00 EDT 2021 · ACS Applied Materials and Interfaces

DOI:https://doi.org/10.1021/acsami.1c02860· OSTI ID:1865533

Mooney, Madison ^[1]; ^[2]; Nyayachavadi, Audithya ^[3]; ^[2]; ^[2]; ^[3]

Univ. of Windsor, ON (Canada); University of Southern Mississippi
Univ. of Southern Mississippi, Hattiesburg, MS (United States)
Univ. of Windsor, ON (Canada)

Semiconducting polymers are at the forefront of next-generation organic electronics due to their robust mechanical and optoelectronic properties. However, their extended π-conjugation often leads to materials with low solubilities in common organic solvents, thus requiring processing in high-boiling-point and toxic halogenated solvents to generate thin-film devices. To address this environmental concern, a natural product-inspired side-chain engineering approach was used to incorporate galactose-containing moieties into semiconducting polymers toward improved processability in greener solvents. Novel isoindigo-based polymers with different ratios of galactose-containing side chains were synthesized to improve the solubilities of the organic semiconductors in alcohol-based solvents. The addition of carbohydrate-containing side chains to π-conjugated polymers was found to considerably impact the intermolecular aggregation of the materials and their microstructures in the solid state as confirmed by atomic force microscopy and grazing-incidence wide-angle X-ray scattering. The charge transport characteristics of the new semiconductors were evaluated by the fabrication of organic field-effect transistors prepared from both toxic halogenated and greener alcohol-based solvents. Importantly, the incorporation of carbohydrate-containing side chains was shown to have very little detrimental impact on the electronic properties of the polymer when processed from green solvents.

View Accepted Manuscript (DOE)

Research Organization:: Univ. of Southern Mississippi, Hattiesburg, MS (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES); NSERC; Canada Foundation for Innovation; Ontario Research Fund

Grant/Contract Number:: SC0019361

OSTI ID:: 1865533

Alternate ID(s):: OSTI ID: 1853111
OSTI ID: 1985340

Journal Information:: ACS Applied Materials and Interfaces, Journal Name: ACS Applied Materials and Interfaces Journal Issue: 21 Vol. 13; ISSN 1944-8244

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

References (55)

Anisotropic Structure and Charge Transport in Highly Strain-Aligned Regioregular Poly(3-hexylthiophene) O'Connor, Brendan; Kline, R. Joseph; Conrad, Brad R. Advanced Functional Materials, Vol. 21, Issue 19 https://doi.org/10.1002/adfm.201100904	journal	August 2011
Taming Charge Transport in Semiconducting Polymers with Branched Alkyl Side Chains Schroeder, Bob C.; Kurosawa, Tadanori; Fu, Tianren Advanced Functional Materials, Vol. 27, Issue 34 https://doi.org/10.1002/adfm.201701973	journal	July 2017
Tacky Elastomers to Enable Tear‐Resistant and Autonomous Self‐Healing Semiconductor Composites Zhang, Song; Cheng, Yu‐Hsuan; Galuska, Luke Advanced Functional Materials, Vol. 30, Issue 27 https://doi.org/10.1002/adfm.202000663	journal	May 2020
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
25th Anniversary Article: The Evolution of Electronic Skin (E-Skin): A Brief History, Design Considerations, and Recent Progress Hammock, Mallory L.; Chortos, Alex; Tee, Benjamin C. -K. Advanced Materials, Vol. 25, Issue 42 https://doi.org/10.1002/adma.201302240	journal	October 2013
Fiber-Based Wearable Electronics: A Review of Materials, Fabrication, Devices, and Applications Zeng, Wei; Shu, Lin; Li, Qiao Advanced Materials, Vol. 26, Issue 31 https://doi.org/10.1002/adma.201400633	journal	June 2014
Stretchable Polymer Semiconductors for Plastic Electronics Wang, Ging-Ji Nathan; Gasperini, Andrea; Bao, Zhenan Advanced Electronic Materials, Vol. 4, Issue 2 https://doi.org/10.1002/aelm.201700429	journal	January 2018
The Critical Role of Electron‐Donating Thiophene Groups on the Mechanical and Thermal Properties of Donor–Acceptor Semiconducting Polymers Zhang, Song; Ocheje, Michael U.; Huang, Lifeng Advanced Electronic Materials, Vol. 5, Issue 5 https://doi.org/10.1002/aelm.201800899	journal	March 2019
Nonaromatic Green‐Solvent‐Processable, Dopant‐Free, and Lead‐Capturable Hole Transport Polymers in Perovskite Solar Cells with High Efficiency Lee, Junwoo; Kim, Guan‐Woo; Kim, Minjun Advanced Energy Materials, Vol. 10, Issue 8 https://doi.org/10.1002/aenm.201902662	journal	January 2020
Galactose toxicity in animals Lai, Kent; Elsas, Louis J.; Wierenga, Klaas J. IUBMB Life, Vol. 61, Issue 11 https://doi.org/10.1002/iub.262	journal	November 2009
Probing the Viscoelastic Property of Pseudo Free-Standing Conjugated Polymeric Thin Films Zhang, Song; Ocheje, Michael U.; Luo, Shaochuan Macromolecular Rapid Communications, Vol. 39, Issue 14 https://doi.org/10.1002/marc.201800092	journal	May 2018
Recent Advances in Mechanically Robust and Stretchable Bulk Heterojunction Polymer Solar Cells St. Onge, P. Blake J.; Ocheje, Michael U.; Selivanova, Mariia The Chemical Record, Vol. 19, Issue 6 https://doi.org/10.1002/tcr.201800163	journal	December 2018
Prodrug strategies to overcome poor water solubility Stella, Valentino J.; Nti-Addae, Kwame W. Advanced Drug Delivery Reviews, Vol. 59, Issue 7 https://doi.org/10.1016/j.addr.2007.05.013	journal	July 2007
A review of glycosylated carriers for drug delivery Jain, Keerti; Kesharwani, Prashant; Gupta, Umesh Biomaterials, Vol. 33, Issue 16 https://doi.org/10.1016/j.biomaterials.2012.02.033	journal	June 2012
Internet of Things (IoT): A vision, architectural elements, and future directions Gubbi, Jayavardhana; Buyya, Rajkumar; Marusic, Slaven Future Generation Computer Systems, Vol. 29, Issue 7 https://doi.org/10.1016/j.future.2013.01.010	journal	September 2013
Synthesis of betulinic acid acyl glucuronide for application in anticancer prodrug monotherapy Gauthier, Charles; Legault, Jean; Rondeau, Simon Tetrahedron Letters, Vol. 50, Issue 9 https://doi.org/10.1016/j.tetlet.2008.12.043	journal	March 2009
All-Polymer Solar Cells Employing Non-Halogenated Solvent and Additive Zhou, Yan; Gu, Kevin L.; Gu, Xiaodan Chemistry of Materials, Vol. 28, Issue 14 https://doi.org/10.1021/acs.chemmater.6b01776	journal	July 2016
Effect of Acceptor Unit Length and Planarity on the Optoelectronic Properties of Isoindigo–Thiophene Donor–Acceptor Polymers Randell, Nicholas M.; Radford, Chase L.; Yang, Jinli Chemistry of Materials, Vol. 30, Issue 14 https://doi.org/10.1021/acs.chemmater.8b02535	journal	June 2018
Structure–Property Relationships Directing Transport and Charge Separation in Isoindigo Polymers Grand, Caroline; Baek, Sujin; Lai, Tzung-Han Macromolecules, Vol. 49, Issue 11 https://doi.org/10.1021/acs.macromol.6b00540	journal	May 2016
Ethanol-Processable, Highly Crystalline Conjugated Polymers for Eco-Friendly Fabrication of Organic Transistors and Solar Cells Nguyen, Thanh Luan; Lee, Changyeon; Kim, Hyoeun Macromolecules, Vol. 50, Issue 11 https://doi.org/10.1021/acs.macromol.7b00452	journal	May 2017
Soft Poly(butyl acrylate) Side Chains toward Intrinsically Stretchable Polymeric Semiconductors for Field-Effect Transistor Applications Wen, Han-Fang; Wu, Hung-Chin; Aimi, Junko Macromolecules, Vol. 50, Issue 13 https://doi.org/10.1021/acs.macromol.7b00860	journal	June 2017
Amide-Containing Alkyl Chains in Conjugated Polymers: Effect on Self-Assembly and Electronic Properties Ocheje, Michael U.; Charron, Brynn P.; Cheng, Yu-Hsuan Macromolecules, Vol. 51, Issue 4 https://doi.org/10.1021/acs.macromol.7b02393	journal	February 2018
Morphology and Electronic Properties of Semiconducting Polymer and Branched Polyethylene Blends Selivanova, Mariia; Chuang, Ching-Heng; Billet, Blandine ACS Applied Materials & Interfaces, Vol. 11, Issue 13 https://doi.org/10.1021/acsami.8b22746	journal	March 2019
Green-Solvent-Processed Conjugated Polymers for Organic Solar Cells: The Impact of Oligoethylene Glycol Side Chains Chen, Zheng; Yan, Liang; Rech, Jeromy James ACS Applied Polymer Materials, Vol. 1, Issue 4 https://doi.org/10.1021/acsapm.9b00044	journal	March 2019
Aqueous Processing for Printed Organic Electronics: Conjugated Polymers with Multistage Cleavable Side Chains Schmatz, Brian; Yuan, Zhibo; Lang, Augustus W. ACS Central Science, Vol. 3, Issue 9 https://doi.org/10.1021/acscentsci.7b00232	journal	August 2017
Oligoethylene-Glycol-Functionalized Polyoxythiophenes for Cell Engineering: Syntheses, Characterizations, and Cell Compatibilities Zhao, Haichao; Zhu, Bo; Sekine, Jun ACS Applied Materials & Interfaces, Vol. 4, Issue 2 https://doi.org/10.1021/am2012905	journal	January 2012
Direct (Hetero)Arylation: A New Tool for Polymer Chemists Mercier, Lauren G.; Leclerc, Mario Accounts of Chemical Research, Vol. 46, Issue 7 https://doi.org/10.1021/ar3003305	journal	April 2013
Design, Synthesis, and Structure–Property Relationships of Isoindigo-Based Conjugated Polymers Lei, Ting; Wang, Jie-Yu; Pei, Jian Accounts of Chemical Research, Vol. 47, Issue 4 https://doi.org/10.1021/ar400254j	journal	February 2014
Thin Film Deposition, Patterning, and Printing in Organic Thin Film Transistors Ling, Mang Mang; Bao, Zhenan Chemistry of Materials, Vol. 16, Issue 23, p. 4824-4840 https://doi.org/10.1021/cm0496117	journal	October 2004
Molecularly Stretchable Electronics Savagatrup, Suchol; Printz, Adam D.; O’Connor, Timothy F. Chemistry of Materials, Vol. 26, Issue 10 https://doi.org/10.1021/cm501021v	journal	May 2014
Water-Soluble Conjugated Polymers for Imaging, Diagnosis, and Therapy Zhu, Chunlei; Liu, Libing; Yang, Qiong Chemical Reviews, Vol. 112, Issue 8 https://doi.org/10.1021/cr200263w	journal	May 2012
Design and Synthesis of Monofunctionalized, Water-Soluble Conjugated Polymers for Biosensing and Imaging Applications Traina, Christopher A.; Bakus, Ronald C.; Bazan, Guillermo C. Journal of the American Chemical Society, Vol. 133, Issue 32 https://doi.org/10.1021/ja202877q	journal	August 2011
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
Significant Improvement of Semiconducting Performance of the Diketopyrrolopyrrole–Quaterthiophene Conjugated Polymer through Side-Chain Engineering via Hydrogen-Bonding Yao, Jingjing; Yu, Chenmin; Liu, Zitong Journal of the American Chemical Society, Vol. 138, Issue 1 https://doi.org/10.1021/jacs.5b09737	journal	December 2015
FTIR Study on Hydrogen-Bonding Interactions in Biodegradable Polymer Blends of Poly(3-hydroxybutyrate) and Poly(4-vinylphenol) Guo, Longhai; Sato, Harumi; Hashimoto, Takeji Macromolecules, Vol. 43, Issue 8 https://doi.org/10.1021/ma100307m	journal	March 2010
Pd ₂ (dba) ₃ as a Precursor of Soluble Metal Complexes and Nanoparticles: Determination of Palladium Active Species for Catalysis and Synthesis Zalesskiy, Sergey S.; Ananikov, Valentine P. Organometallics, Vol. 31, Issue 6 https://doi.org/10.1021/om201217r	journal	March 2012
Intrinsically stretchable and healable semiconducting polymer for organic transistors Oh, Jin Young; Rondeau-Gagné, Simon; Chiu, Yu-Cheng Nature, Vol. 539, Issue 7629 https://doi.org/10.1038/nature20102	journal	November 2016
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
Skin-inspired highly stretchable and conformable matrix networks for multifunctional sensing Hua, Qilin; Sun, Junlu; Liu, Haitao Nature Communications, Vol. 9, Issue 1 https://doi.org/10.1038/s41467-017-02685-9	journal	January 2018
Materials capability and device performance in flexible electronics for the Internet of Things Zhan, Yiqiang; Mei, Yongfeng; Zheng, Lirong J. Mater. Chem. C, Vol. 2, Issue 7 https://doi.org/10.1039/C3TC31765J	journal	January 2014
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
A high mobility DPP-based polymer obtained via direct (hetero)arylation polymerization Pouliot, Jean-Rémi; Sun, Bin; Leduc, Mikaël Polymer Chemistry, Vol. 6, Issue 2 https://doi.org/10.1039/C4PY01222D	journal	January 2015
Realizing the full potential of conjugated polymers: innovation in polymer synthesis Morin, Pierre-Olivier; Bura, Thomas; Leclerc, Mario Materials Horizons, Vol. 3, Issue 1 https://doi.org/10.1039/C5MH00164A	journal	January 2016
Toward organic electronics with properties inspired by biological tissue O'Connor, Timothy F.; Rajan, Kirtana M.; Printz, Adam D. Journal of Materials Chemistry B, Vol. 3, Issue 25 https://doi.org/10.1039/C5TB00173K	journal	January 2015
Effect of the alkyl spacer length on the electrical performance of diketopyrrolopyrrole-thiophene vinylene thiophene polymer semiconductors Yu, Hojeong; Park, Kwang Hun; Song, Inho Journal of Materials Chemistry C, Vol. 3, Issue 44 https://doi.org/10.1039/C5TC02565F	journal	January 2015
Influence of amide-containing side chains on the mechanical properties of diketopyrrolopyrrole-based polymers Ocheje, Michael U.; Selivanova, Mariia; Zhang, Song Polymer Chemistry, Vol. 9, Issue 46 https://doi.org/10.1039/C8PY01207E	journal	January 2018
Non-halogenated solution-processed ambipolar plastic transistors based on conjugated polymers prepared by asymmetric donor engineering Song, Inho; Kim, Hyun-Woo; Ahn, Jaeyong Journal of Materials Chemistry C, Vol. 7, Issue 47 https://doi.org/10.1039/C9TC04808A	journal	January 2019
Eco-friendly semiconducting polymers: from greener synthesis to greener processability Mooney, Madison; Nyayachavadi, Audithya; Rondeau-Gagné, Simon Journal of Materials Chemistry C, Vol. 8, Issue 42 https://doi.org/10.1039/D0TC04085A	journal	January 2020
Expanding GSK's solvent selection guide – embedding sustainability into solvent selection starting at medicinal chemistry Henderson, Richard K.; Jiménez-González, Concepción; Constable, David J. C. Green Chemistry, Vol. 13, Issue 4 https://doi.org/10.1039/c0gc00918k	journal	January 2011
Inkjet printing of organic electronics – comparison of deposition techniques and state-of-the-art developments Teichler, Anke; Perelaer, Jolke; Schubert, Ulrich S. Journal of Materials Chemistry C, Vol. 1, Issue 10 https://doi.org/10.1039/c2tc00255h	journal	January 2013
Biocompatible and totally disintegrable semiconducting polymer for ultrathin and ultralightweight transient electronics Lei, Ting; Guan, Ming; Liu, Jia Proceedings of the National Academy of Sciences, Vol. 114, Issue 20 https://doi.org/10.1073/pnas.1701478114	journal	May 2017
Stretchable electronics: materials, architectures and integrations Ahn, Jong-Hyun; Je, Jung Ho Journal of Physics D: Applied Physics, Vol. 45, Issue 10 https://doi.org/10.1088/0022-3727/45/10/103001	journal	February 2012
Stretchable electronics: recent progress in the preparation of stretchable and self-healing semiconducting conjugated polymers Ocheje, Michael U.; Charron, Brynn P.; Nyayachavadi, Audithya Flexible and Printed Electronics, Vol. 2, Issue 4 https://doi.org/10.1088/2058-8585/aa9c9b	journal	December 2017
Technologies for Printing Sensors and Electronics Over Large Flexible Substrates: A Review Khan, Saleem; Lorenzelli, Leandro; Dahiya, Ravinder S. IEEE Sensors Journal, Vol. 15, Issue 6 https://doi.org/10.1109/JSEN.2014.2375203	journal	June 2015
Sensor Mania! The Internet of Things, Wearable Computing, Objective Metrics, and the Quantified Self 2.0 Swan, Melanie Journal of Sensor and Actuator Networks, Vol. 1, Issue 3 https://doi.org/10.3390/jsan1030217	journal	November 2012

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