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Asymmetric side-chain engineering in semiconducting polymers: a platform for greener processing and post-functionalization of organic electronics

Journal Article · · Polymer Chemistry
DOI:https://doi.org/10.1039/d2py01244h· OSTI ID:1922149
 [1];  [2];  [2];  [2];  [3];  [4];  [5];  [5];  [4];  [3];  [2]
  1. Univ. of Windsor, Ontario (Canada); a. School of Polymer Science and Engineering, Center for Optoelectronic Materials and Devices, The University of Southern Mississippi, Hattiesburg, MS 39406, USA.
  2. Univ. of Windsor, Ontario (Canada)
  3. Univ. of Southern Mississippi, Hattiesburg, MS (United States)
  4. National Taiwan Univ. of Science and Technology, Taipei (Taiwan)
  5. Argonne National Lab. (ANL), Lemont, IL (United States)
+ Show Author Affiliations
Organic semiconducting polymers are a powerful platform for the design of next-generation technologies due to their excellent optoelectronic properties and solution processability, allowing access to low-cost and scalable manufacturing techniques such as spin-coating, slot-die coating and roll-to-roll printing. However, their extended π-conjugation results in low solubility, requiring the use of toxic halogenated solvents to generate thin films and devices. Furthermore, accessible post-functionalization of semiconductors toward the development of multifunctional devices and sensors remains a challenge due to limited solid-state chemistry for alkyl side chains. In this work, an asymmetric side-chain engineering approach was used to introduce terminal hydroxyl moieties alongside traditional solubilizing branched alkyl chains into an isoindigo-based polymer. The hydroxyl moieties led to significantly improved processability in alcohol-based solvents without sacrificing electronic performance in thin film organic field-effect transistors. Solid state morphologies of the thin films processed from both alcohol-based and traditional halogenated solvents were further characterized using atomic force microscopy and grazing incidence wide angle X-ray scattering. Additionally, Cryo-EM was utilized in order to characterize the role of asymmetric side-chain functionality in solution state aggregation. The versatility of this design was further probed using fluorescein isothiocyanate to directly functionalize the asymmetric polymer in thin film. Furthermore, this facile solid-state post-functionalization further demonstrates asymmetric side-chain engineering to be a viable approach toward the development of sustainably manufactured multifunctional electronics.
Research Organization:
Univ. of Southern Mississippi, Hattiesburg, MS (United States)
Sponsoring Organization:
USDOE Office of Science (SC), Basic Energy Sciences (BES)
Grant/Contract Number:
SC0019361; AC02-06CH11357
OSTI ID:
1922149
Alternate ID(s):
OSTI ID: 2429684
OSTI ID: 1907897
OSTI ID: 1985431
Journal Information:
Polymer Chemistry, Journal Name: Polymer Chemistry Journal Issue: 5 Vol. 14; ISSN 1759-9954
Publisher:
Royal Society of ChemistryCopyright Statement
Country of Publication:
United States
Language:
English

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