Enhancing the Solubility of Semiconducting Polymers in Eco-Friendly Solvents with Carbohydrate-Containing Side Chains
Abstract
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.
- Authors:
-
[2];
[2];
[2];
[1]
- Univ. of Windsor, ON (Canada)
- Univ. of Southern Mississippi, Hattiesburg, MS (United States)
- Publication Date:
- Research Org.:
- Univ. of Southern Mississippi, Hattiesburg, MS (United States); University of Southern Mississippi, Hattiesburg, MS (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC), Basic Energy Sciences (BES); Natural Sciences and Engineering Research Council of Canada (NSERC); Canada Foundation for Innovation; Ontario Research Fund
- OSTI Identifier:
- 1865533
- Alternate Identifier(s):
- OSTI ID: 1985340
- Grant/Contract Number:
- SC0019361; OIA-1757220; NETGP 508526-17; RGPIN-2017-06611
- Resource Type:
- Accepted Manuscript
- Journal Name:
- ACS Applied Materials and Interfaces
- Additional Journal Information:
- Journal Volume: 13; Journal Issue: 21; Journal ID: ISSN 1944-8244
- Publisher:
- American Chemical Society (ACS)
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; green electronics; semiconducting polymers; organic field-effect transistors; side-chain engineering; processing of π-conjugated polymers
Citation Formats
Mooney, Madison, Wang, Yunfei, Nyayachavadi, Audithya, Zhang, Song, Gu, Xiaodan, and Rondeau-Gagné, Simon. Enhancing the Solubility of Semiconducting Polymers in Eco-Friendly Solvents with Carbohydrate-Containing Side Chains. United States: N. p., 2021.
Web. doi:10.1021/acsami.1c02860.
Mooney, Madison, Wang, Yunfei, Nyayachavadi, Audithya, Zhang, Song, Gu, Xiaodan, & Rondeau-Gagné, Simon. Enhancing the Solubility of Semiconducting Polymers in Eco-Friendly Solvents with Carbohydrate-Containing Side Chains. United States. https://doi.org/10.1021/acsami.1c02860
Mooney, Madison, Wang, Yunfei, Nyayachavadi, Audithya, Zhang, Song, Gu, Xiaodan, and Rondeau-Gagné, Simon. Wed .
"Enhancing the Solubility of Semiconducting Polymers in Eco-Friendly Solvents with Carbohydrate-Containing Side Chains". United States. https://doi.org/10.1021/acsami.1c02860. https://www.osti.gov/servlets/purl/1865533.
@article{osti_1865533,
title = {Enhancing the Solubility of Semiconducting Polymers in Eco-Friendly Solvents with Carbohydrate-Containing Side Chains},
author = {Mooney, Madison and Wang, Yunfei and Nyayachavadi, Audithya and Zhang, Song and Gu, Xiaodan and Rondeau-Gagné, Simon},
abstractNote = {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.},
doi = {10.1021/acsami.1c02860},
journal = {ACS Applied Materials and Interfaces},
number = 21,
volume = 13,
place = {United States},
year = {Wed May 19 00:00:00 EDT 2021},
month = {Wed May 19 00:00:00 EDT 2021}
}
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