Solvent Composition Directing Click-Functionalization at the Surface or in the Bulk of Azide-Modified PEDOT

Research output: Contribution to journalJournal articleResearchpeer-review

Abstract

Thin films of the conducting polymer poly(3,4-(1-azidomethylethylene)dioxythiophene) tosylate (PEDOT−N3) can be functionalized by reaction with alkynated reagents in aqueous solutions. Reaction in pure water resulted in surface specific modification of PEDOT−N3 films, whereas both surface and bulk reaction was achieved in solvent mixtures of water and DMSO. These reaction patterns were confirmed by a combination of AFM and XPS measurements on the front- and back-side of the film. The phenomenon is attributed to a strong dependence of the swelling of PEDOT−N3 on the solvent mixture used. Liquid AFM studies showed increasing film thickness with increasing DMSO content, with the measured thickness in pure DMSO being >250% of the thickness in pure water. A similar, but less pronounced, behavior was observed for unmodified poly(3,4-ethylenedioxythiophene) tosylate (PEDOT). High-density grafting of a number of alkynated compounds onto PEDOT−N3 was achieved via controlled swelling of the polymer. In particular, grafting of alkynated poly(ethylene glycol) (PEG) was optimized to minimize protein adsorption to the conductive polymer surface. Intermediate swelling of PEDOT−N3 during the reaction, using ∼50% DMSO, resulted in the formation of a dense PEG surface layer with low protein adhesiveness without adversely affecting the conductive properties of the film.
Original languageEnglish
JournalMacromolecules
Volume44
Issue number3
Pages (from-to)495-501
ISSN0024-9297
DOIs
Publication statusPublished - 2011

Cite this

@article{e7728b600df84d6585c71169c0b5f633,
title = "Solvent Composition Directing Click-Functionalization at the Surface or in the Bulk of Azide-Modified PEDOT",
abstract = "Thin films of the conducting polymer poly(3,4-(1-azidomethylethylene)dioxythiophene) tosylate (PEDOT−N3) can be functionalized by reaction with alkynated reagents in aqueous solutions. Reaction in pure water resulted in surface specific modification of PEDOT−N3 films, whereas both surface and bulk reaction was achieved in solvent mixtures of water and DMSO. These reaction patterns were confirmed by a combination of AFM and XPS measurements on the front- and back-side of the film. The phenomenon is attributed to a strong dependence of the swelling of PEDOT−N3 on the solvent mixture used. Liquid AFM studies showed increasing film thickness with increasing DMSO content, with the measured thickness in pure DMSO being >250{\%} of the thickness in pure water. A similar, but less pronounced, behavior was observed for unmodified poly(3,4-ethylenedioxythiophene) tosylate (PEDOT). High-density grafting of a number of alkynated compounds onto PEDOT−N3 was achieved via controlled swelling of the polymer. In particular, grafting of alkynated poly(ethylene glycol) (PEG) was optimized to minimize protein adsorption to the conductive polymer surface. Intermediate swelling of PEDOT−N3 during the reaction, using ∼50{\%} DMSO, resulted in the formation of a dense PEG surface layer with low protein adhesiveness without adversely affecting the conductive properties of the film.",
author = "Lind, {Johan Ulrik} and Hansen, {Thomas Steen} and Daugaard, {Anders Egede} and S{\o}ren Hvilsted and Andresen, {Thomas Lars} and Larsen, {Niels Bent}",
year = "2011",
doi = "10.1021/ma102149u",
language = "English",
volume = "44",
pages = "495--501",
journal = "Macromolecules",
issn = "0024-9297",
publisher = "American Chemical Society",
number = "3",

}

Solvent Composition Directing Click-Functionalization at the Surface or in the Bulk of Azide-Modified PEDOT. / Lind, Johan Ulrik; Hansen, Thomas Steen; Daugaard, Anders Egede; Hvilsted, Søren; Andresen, Thomas Lars; Larsen, Niels Bent.

In: Macromolecules, Vol. 44, No. 3, 2011, p. 495-501.

Research output: Contribution to journalJournal articleResearchpeer-review

TY - JOUR

T1 - Solvent Composition Directing Click-Functionalization at the Surface or in the Bulk of Azide-Modified PEDOT

AU - Lind, Johan Ulrik

AU - Hansen, Thomas Steen

AU - Daugaard, Anders Egede

AU - Hvilsted, Søren

AU - Andresen, Thomas Lars

AU - Larsen, Niels Bent

PY - 2011

Y1 - 2011

N2 - Thin films of the conducting polymer poly(3,4-(1-azidomethylethylene)dioxythiophene) tosylate (PEDOT−N3) can be functionalized by reaction with alkynated reagents in aqueous solutions. Reaction in pure water resulted in surface specific modification of PEDOT−N3 films, whereas both surface and bulk reaction was achieved in solvent mixtures of water and DMSO. These reaction patterns were confirmed by a combination of AFM and XPS measurements on the front- and back-side of the film. The phenomenon is attributed to a strong dependence of the swelling of PEDOT−N3 on the solvent mixture used. Liquid AFM studies showed increasing film thickness with increasing DMSO content, with the measured thickness in pure DMSO being >250% of the thickness in pure water. A similar, but less pronounced, behavior was observed for unmodified poly(3,4-ethylenedioxythiophene) tosylate (PEDOT). High-density grafting of a number of alkynated compounds onto PEDOT−N3 was achieved via controlled swelling of the polymer. In particular, grafting of alkynated poly(ethylene glycol) (PEG) was optimized to minimize protein adsorption to the conductive polymer surface. Intermediate swelling of PEDOT−N3 during the reaction, using ∼50% DMSO, resulted in the formation of a dense PEG surface layer with low protein adhesiveness without adversely affecting the conductive properties of the film.

AB - Thin films of the conducting polymer poly(3,4-(1-azidomethylethylene)dioxythiophene) tosylate (PEDOT−N3) can be functionalized by reaction with alkynated reagents in aqueous solutions. Reaction in pure water resulted in surface specific modification of PEDOT−N3 films, whereas both surface and bulk reaction was achieved in solvent mixtures of water and DMSO. These reaction patterns were confirmed by a combination of AFM and XPS measurements on the front- and back-side of the film. The phenomenon is attributed to a strong dependence of the swelling of PEDOT−N3 on the solvent mixture used. Liquid AFM studies showed increasing film thickness with increasing DMSO content, with the measured thickness in pure DMSO being >250% of the thickness in pure water. A similar, but less pronounced, behavior was observed for unmodified poly(3,4-ethylenedioxythiophene) tosylate (PEDOT). High-density grafting of a number of alkynated compounds onto PEDOT−N3 was achieved via controlled swelling of the polymer. In particular, grafting of alkynated poly(ethylene glycol) (PEG) was optimized to minimize protein adsorption to the conductive polymer surface. Intermediate swelling of PEDOT−N3 during the reaction, using ∼50% DMSO, resulted in the formation of a dense PEG surface layer with low protein adhesiveness without adversely affecting the conductive properties of the film.

U2 - 10.1021/ma102149u

DO - 10.1021/ma102149u

M3 - Journal article

VL - 44

SP - 495

EP - 501

JO - Macromolecules

JF - Macromolecules

SN - 0024-9297

IS - 3

ER -