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Functional Conducting Polymers via Thiol-ene Chemistry.

Feldman KE, Martin DC - Biosensors (Basel) (2012)

Bottom Line: We demonstrate here that thiol-ene chemistry can be used to provide side-chain functionalized monomers based on 3,4-propylenedioxythiophene (ProDOT) containing ionic, neutral, hydrophobic, and hydrophilic side chains.These monomers were polymerized either chemically or electro-chemically to give soluble materials or conductive films, respectively.This strategy provides for facile tuning of the solubility, film surface chemistry, and film morphology of this class of conducting polymers.

View Article: PubMed Central - PubMed

Affiliation: Department of Materials Science and Engineering, University of Delaware, Newark, DE 19716, USA. katiefeldman0@gmail.com.

ABSTRACT
We demonstrate here that thiol-ene chemistry can be used to provide side-chain functionalized monomers based on 3,4-propylenedioxythiophene (ProDOT) containing ionic, neutral, hydrophobic, and hydrophilic side chains. All reactions gave high yields and purification could generally be accomplished through precipitation. These monomers were polymerized either chemically or electro-chemically to give soluble materials or conductive films, respectively. This strategy provides for facile tuning of the solubility, film surface chemistry, and film morphology of this class of conducting polymers.

No MeSH data available.


UV-Vis spectra of water and organic soluble polymers.
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biosensors-02-00305-f004: UV-Vis spectra of water and organic soluble polymers.

Mentions: Monomer functionalization via thiol-ene chemistry is also an effective strategy to synthesize soluble polymers. The utility of soluble conducting polymers is demonstrated by the significant commercial success of PEDOT/PSS dispersions (Clevios™ P), which can be spin coated to give transparent conductive layers on a variety of substrates. Using the current strategy, ProDOT-SO3Na was polymerized in solution with FeCl3, precipitated with methanol, and purified by dialysis to give a fully water soluble material. Similarly, ethylhexyl-ProDOT was polymerized in CHCl3 solution using FeCl3 and precipitated with methanol to give a polymer soluble in CHCl3, THF, and acetonitrile. UV-Vis spectra (Figure 4) of the two polymers show broad absorption characteristic of the partially oxidized state of the polymers.


Functional Conducting Polymers via Thiol-ene Chemistry.

Feldman KE, Martin DC - Biosensors (Basel) (2012)

UV-Vis spectra of water and organic soluble polymers.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4263549&req=5

biosensors-02-00305-f004: UV-Vis spectra of water and organic soluble polymers.
Mentions: Monomer functionalization via thiol-ene chemistry is also an effective strategy to synthesize soluble polymers. The utility of soluble conducting polymers is demonstrated by the significant commercial success of PEDOT/PSS dispersions (Clevios™ P), which can be spin coated to give transparent conductive layers on a variety of substrates. Using the current strategy, ProDOT-SO3Na was polymerized in solution with FeCl3, precipitated with methanol, and purified by dialysis to give a fully water soluble material. Similarly, ethylhexyl-ProDOT was polymerized in CHCl3 solution using FeCl3 and precipitated with methanol to give a polymer soluble in CHCl3, THF, and acetonitrile. UV-Vis spectra (Figure 4) of the two polymers show broad absorption characteristic of the partially oxidized state of the polymers.

Bottom Line: We demonstrate here that thiol-ene chemistry can be used to provide side-chain functionalized monomers based on 3,4-propylenedioxythiophene (ProDOT) containing ionic, neutral, hydrophobic, and hydrophilic side chains.These monomers were polymerized either chemically or electro-chemically to give soluble materials or conductive films, respectively.This strategy provides for facile tuning of the solubility, film surface chemistry, and film morphology of this class of conducting polymers.

View Article: PubMed Central - PubMed

Affiliation: Department of Materials Science and Engineering, University of Delaware, Newark, DE 19716, USA. katiefeldman0@gmail.com.

ABSTRACT
We demonstrate here that thiol-ene chemistry can be used to provide side-chain functionalized monomers based on 3,4-propylenedioxythiophene (ProDOT) containing ionic, neutral, hydrophobic, and hydrophilic side chains. All reactions gave high yields and purification could generally be accomplished through precipitation. These monomers were polymerized either chemically or electro-chemically to give soluble materials or conductive films, respectively. This strategy provides for facile tuning of the solubility, film surface chemistry, and film morphology of this class of conducting polymers.

No MeSH data available.