Synthesis and properties of polythiophene bearing an alkylsulfonic acid ester at the side chain

15 December 2023, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Introduction of an alkylsulfonic acid moiety into the side chain of polythiophene was carried out. Synthesis of 2,5-dihalothiophene bearing an alkylsulfonate group at the 3-position was performed. The reaction of 2-chloro-5-iodothiophene with a Grignard reagent to form organometallic monomer of the corresponding thiophene followed by nickel(II)-catalyzed cross-coupling polymerization lead to head-to-tail-type regioregular polythiophene. The ester group at the side chain was converted into alkali metal sulfonate by treatment with NaI or metal hydroxides (Li, Na, K). The obtained metal salts were successfully transformed to sulfonic acid by the treatment with ion exchange resin. The electric conductivity of the regioregular polythiophene bearing sulfonic acid was remarkably improved ca. 102 times from the corresponding metal salts. (106 times higher than sulfonate ester)

Keywords

Alkylsulfonic acid
polythiophene
Ni catalyst
cross-coupling polymerization
electric conductivity

Supplementary materials

Title
Description
Actions
Title
Supporting Information
Description
Experimental details, SEC profiles of polythiophene, Thermal properties, UV-vis-nir spectrum of polythiophene thin film, and copies of NMR spectra (PDF)
Actions

Comments

Comments are not moderated before they are posted, but they can be removed by the site moderators if they are found to be in contravention of our Commenting Policy [opens in a new tab] - please read this policy before you post. Comments should be used for scholarly discussion of the content in question. You can find more information about how to use the commenting feature here [opens in a new tab] .
This site is protected by reCAPTCHA and the Google Privacy Policy [opens in a new tab] and Terms of Service [opens in a new tab] apply.