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

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dc.contributor.authorHebert, David D.
dc.contributor.authorNaley, Michael A.
dc.contributor.authorCunningham, Carter C.
dc.contributor.authorSharp, David
dc.contributor.authorMurphy, Emma
dc.contributor.authorStanton, Venus
dc.contributor.authorIrvin, Jennifer A.
dc.date.accessioned2021-10-18T13:19:57Z
dc.date.available2021-10-18T13:19:57Z
dc.date.issued2021-10-16
dc.description.abstractPolythiophenes (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.
dc.description.departmentChemistry and Biochemistry
dc.formatText
dc.format.extent15 pages
dc.format.medium1 file (.pdf)
dc.identifier.citationHebert, D. D., Naley, M. A., Cunningham, C. C., Sharp, D. J., Murphy, E. M., Stanton, V., & Irvin, J. A. (2021). Enabling conducting polymer applications: Methods for achieving high molecular weight in chemical oxidative polymerization in alkyl- and ether-substituted thiophenes. Materials, 14(20), 6146.
dc.identifier.doihttps://doi.org/10.3390/ma14206146
dc.identifier.issn1996-1944
dc.identifier.urihttps://hdl.handle.net/10877/14664
dc.language.isoen
dc.publisherMultidisciplinary Digital Publishing Institute
dc.rights.licenseThis work is licensed under a Creative Commons Attribution 4.0 International License.
dc.sourceMaterials, 2021, Vol. 14, No. 20, Article 6146.
dc.subjectpoly(3-hexylthiophene)
dc.subjectpolythiophenes
dc.subjectoxidative polymerization
dc.subjectgel-permeation chromatography
dc.subjecthigh molecular weight
dc.subjectconductive polymers
dc.subjectorder of addition
dc.subjectiron (III) chloride
dc.subjectalkyl-substituted EDOT
dc.subject3,4-dialkoxythiophene
dc.subjectChemistry and Biochemistry
dc.titleEnabling Conducting Polymer Applications: Methods for Achieving High Molecular Weight in Chemical Oxidative Polymerization in Alkyl- and Ether-Substituted Thiophenes
dc.typeArticle

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