Enabling Conducting Polymer Applications: Methods for Achieving High Molecular Weight in Chemical Oxidative Polymerization in Alkyl- and Ether-Substituted Thiophenes

Polythiophenes (PTs) constitute a diverse array of promising materials for conducting polymer applications. However, many of the synthetic methods to produce PTs have been optimized only for the prototypical alkyl-substituted example poly(3-hexylthiophene) (P3HT). Improvement of these methods beyond...

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Published inMaterials Vol. 14; no. 20; p. 6146
Main Authors Hebert, David D., Naley, Michael A., Cunningham, Carter C., Sharp, David J., Murphy, Emma E., Stanton, Venus, Irvin, Jennifer A.
Format Journal Article
LanguageEnglish
Published Basel MDPI AG 16.10.2021
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Abstract Polythiophenes (PTs) constitute a diverse array of promising materials for conducting polymer applications. However, many of the synthetic methods to produce PTs have been optimized only for the prototypical alkyl-substituted example poly(3-hexylthiophene) (P3HT). Improvement of these methods beyond P3HT is key to enabling the widespread application of PTs. In this work, P3HT and two ether-substituted PTs poly(2-dodecyl-2H,3H-thieno[3,4-b][1,4]dioxine) (PEDOT-C12) and poly(3,4-bis(hexyloxy)thiophene) (PBHOT) are synthesized by the FeCl3-initiated oxidative method under different conditions. Polymerization was carried out according to a common literature procedure (“reverse addition”) and a modified method (“standard addition”), which differ by the solvent system and the order of addition of reagents to the reaction mixture. Gel-permeation chromatography (GPC) was performed to determine the impact of the different methods on the molecular weights (Mw) and degree of polymerization (Xw) of the polymers relative to polystyrene standards. The standard addition method produced ether-substituted PTs with higher Mw and Xw than those produced using the reverse addition method for sterically unhindered monomers. For P3HT, the highest Mw and Xw were obtained using the reverse addition method. The results show the oxidation potential of the monomer and solution has the greatest impact on the yield and Xw obtained and should be carefully considered when optimizing the reaction conditions for different monomers.
AbstractList Polythiophenes (PTs) constitute a diverse array of promising materials for conducting polymer applications. However, many of the synthetic methods to produce PTs have been optimized only for the prototypical alkyl-substituted example poly(3-hexylthiophene) (P3HT). Improvement of these methods beyond P3HT is key to enabling the widespread application of PTs. In this work, P3HT and two ether-substituted PTs poly(2-dodecyl-2H,3H-thieno[3,4-b][1,4]dioxine) (PEDOT-C12) and poly(3,4-bis(hexyloxy)thiophene) (PBHOT) are synthesized by the FeCl3-initiated oxidative method under different conditions. Polymerization was carried out according to a common literature procedure (“reverse addition”) and a modified method (“standard addition”), which differ by the solvent system and the order of addition of reagents to the reaction mixture. Gel-permeation chromatography (GPC) was performed to determine the impact of the different methods on the molecular weights (Mw) and degree of polymerization (Xw) of the polymers relative to polystyrene standards. The standard addition method produced ether-substituted PTs with higher Mw and Xw than those produced using the reverse addition method for sterically unhindered monomers. For P3HT, the highest Mw and Xw were obtained using the reverse addition method. The results show the oxidation potential of the monomer and solution has the greatest impact on the yield and Xw obtained and should be carefully considered when optimizing the reaction conditions for different monomers.
Polythiophenes (PTs) constitute a diverse array of promising materials for conducting polymer applications. However, many of the synthetic methods to produce PTs have been optimized only for the prototypical alkyl-substituted example poly(3-hexylthiophene) (P3HT). Improvement of these methods beyond P3HT is key to enabling the widespread application of PTs. In this work, P3HT and two ether-substituted PTs poly(2-dodecyl-2H,3H-thieno[3,4-b][1,4]dioxine) (PEDOT-C12) and poly(3,4-bis(hexyloxy)thiophene) (PBHOT) are synthesized by the FeCl 3 -initiated oxidative method under different conditions. Polymerization was carried out according to a common literature procedure (“reverse addition”) and a modified method (“standard addition”), which differ by the solvent system and the order of addition of reagents to the reaction mixture. Gel-permeation chromatography (GPC) was performed to determine the impact of the different methods on the molecular weights (M w ) and degree of polymerization (X w ) of the polymers relative to polystyrene standards. The standard addition method produced ether-substituted PTs with higher M w and X w than those produced using the reverse addition method for sterically unhindered monomers. For P3HT, the highest M w and X w were obtained using the reverse addition method. The results show the oxidation potential of the monomer and solution has the greatest impact on the yield and X w obtained and should be carefully considered when optimizing the reaction conditions for different monomers.
Author Murphy, Emma E
Sharp, David J
Irvin, Jennifer A
Cunningham, Carter C
Naley, Michael A
Hebert, David D
Stanton, Venus
AuthorAffiliation 2 Department of Biology, Texas State University, San Marcos, TX 78666, USA; mnaley6@gmail.com
3 Materials Science, Engineering and Commercialization Program, Texas State University, San Marcos, TX 78666, USA
1 Department of Chemistry and Biochemistry, Texas State University, San Marcos, TX 78666, USA; hebertdavidd@gmail.com (D.D.H.); ccc179@txstate.edu (C.C.C.); davidsharp97@gmail.com (D.J.S.); emmamurphy5693@gmail.com (E.E.M.); v_s136@txstate.edu (V.S.)
AuthorAffiliation_xml – name: 2 Department of Biology, Texas State University, San Marcos, TX 78666, USA; mnaley6@gmail.com
– name: 3 Materials Science, Engineering and Commercialization Program, Texas State University, San Marcos, TX 78666, USA
– name: 1 Department of Chemistry and Biochemistry, Texas State University, San Marcos, TX 78666, USA; hebertdavidd@gmail.com (D.D.H.); ccc179@txstate.edu (C.C.C.); davidsharp97@gmail.com (D.J.S.); emmamurphy5693@gmail.com (E.E.M.); v_s136@txstate.edu (V.S.)
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Snippet Polythiophenes (PTs) constitute a diverse array of promising materials for conducting polymer applications. However, many of the synthetic methods to produce...
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SubjectTerms Conducting polymers
conductive polymers
Degree of polymerization
Ferric chloride
gel-permeation chromatography
high molecular weight
Life sciences
Molecular weight
Monomers
Oxidation
oxidative polymerization
poly(3-hexylthiophene)
Polymerization
Polymers
Polystyrene resins
Polythiophene
polythiophenes
Production methods
Reagents
Solvents
Substitutes
Thiophenes
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Title Enabling Conducting Polymer Applications: Methods for Achieving High Molecular Weight in Chemical Oxidative Polymerization in Alkyl- and Ether-Substituted Thiophenes
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