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Title: Synthesis of Poly(bisisoindigo) Using a Metal-Free Aldol Polymerization for Thin-Film Transistor Applications

Abstract

Typical syntheses of conjugated polymers rely heavily on organometallic reagents and metal-catalyzed cross-coupling reactions. In this paper, we show that an environmentally benign aldol polymerization can be used to synthesize poly(bisisoindigo), an analog of polyisoindigo with a ring-fused structural repeat unit. Owing to its extended conjugation length, poly(bisisoindigo) absorbs across the UV/vis/NIR spectrum, with an absorption tail that reaches 1000 nm. Due to the four electron-deficient lactam units on each repeat unit, poly(bisoindigo) possesses a low-lying LUMO, which lies at -3.94 eV relative to vacuum. Incorporation of the ring-fused monomer unit also lowered the overall torsional strain in the polymer backbone (relative to polyisoindigo), and the polymer was successfully used in prototype unipolar n-channel organic thin-film transistors.

Authors:
 [1];  [2];  [2];  [3];  [1]; ORCiD logo [2]; ORCiD logo [3]; ORCiD logo [1]
  1. Univ. of Saskatchewan, Saskatoon, SK (Canada)
  2. Univ. of Waterloo, ON (Canada)
  3. SLAC National Accelerator Lab., Menlo Park, CA (United States). Stanford Synchrotron Radiation Lightsource (SSRL)
Publication Date:
Research Org.:
SLAC National Accelerator Lab., Menlo Park, CA (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES); Natural Sciences and Engineering Research Council of Canada (NSERC)
OSTI Identifier:
1633862
Grant/Contract Number:  
AC02-76SF00515; RGPIN-2016-04366; RGPIN-2017-03732
Resource Type:
Journal Article: Accepted Manuscript
Journal Name:
ACS Applied Materials and Interfaces
Additional Journal Information:
Journal Volume: 12; Journal Issue: 12; 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; Thin films; Polymerization; Conjugated polymers; Mobility; Polymers

Citation Formats

Ganguly, Anindya, He, Keqiang, Hendsbee, Arthur D., Abdelsamie, Maged, Bennett, Raymond N., Li, Yuning, Toney, Michael F., and Kelly, Timothy L. Synthesis of Poly(bisisoindigo) Using a Metal-Free Aldol Polymerization for Thin-Film Transistor Applications. United States: N. p., 2020. Web. doi:10.1021/acsami.9b23064.
Ganguly, Anindya, He, Keqiang, Hendsbee, Arthur D., Abdelsamie, Maged, Bennett, Raymond N., Li, Yuning, Toney, Michael F., & Kelly, Timothy L. Synthesis of Poly(bisisoindigo) Using a Metal-Free Aldol Polymerization for Thin-Film Transistor Applications. United States. https://doi.org/10.1021/acsami.9b23064
Ganguly, Anindya, He, Keqiang, Hendsbee, Arthur D., Abdelsamie, Maged, Bennett, Raymond N., Li, Yuning, Toney, Michael F., and Kelly, Timothy L. 2020. "Synthesis of Poly(bisisoindigo) Using a Metal-Free Aldol Polymerization for Thin-Film Transistor Applications". United States. https://doi.org/10.1021/acsami.9b23064. https://www.osti.gov/servlets/purl/1633862.
@article{osti_1633862,
title = {Synthesis of Poly(bisisoindigo) Using a Metal-Free Aldol Polymerization for Thin-Film Transistor Applications},
author = {Ganguly, Anindya and He, Keqiang and Hendsbee, Arthur D. and Abdelsamie, Maged and Bennett, Raymond N. and Li, Yuning and Toney, Michael F. and Kelly, Timothy L.},
abstractNote = {Typical syntheses of conjugated polymers rely heavily on organometallic reagents and metal-catalyzed cross-coupling reactions. In this paper, we show that an environmentally benign aldol polymerization can be used to synthesize poly(bisisoindigo), an analog of polyisoindigo with a ring-fused structural repeat unit. Owing to its extended conjugation length, poly(bisisoindigo) absorbs across the UV/vis/NIR spectrum, with an absorption tail that reaches 1000 nm. Due to the four electron-deficient lactam units on each repeat unit, poly(bisoindigo) possesses a low-lying LUMO, which lies at -3.94 eV relative to vacuum. Incorporation of the ring-fused monomer unit also lowered the overall torsional strain in the polymer backbone (relative to polyisoindigo), and the polymer was successfully used in prototype unipolar n-channel organic thin-film transistors.},
doi = {10.1021/acsami.9b23064},
url = {https://www.osti.gov/biblio/1633862}, journal = {ACS Applied Materials and Interfaces},
issn = {1944-8244},
number = 12,
volume = 12,
place = {United States},
year = {2020},
month = {3}
}

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