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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.


Cyclic voltammetry data for functional ProDOT films electrochemically deposited from solutions of (A) 10% ProDOT-CO2H + 90% ProDOT and 20% ProDOT-CO2H + 80% ProDOT, (B) 10% ProDOT-NH2 + 90% ProDOT and 20% ProDOT-NH2 + 80% ProDOT, (C) 10% ProDOT-glycerol + 90% ProDOT and 20% ProDOT-glycerol + 80% ProDOT, and (D) 10% ProDOT-SO3Na + 90% ProDOT and 20% ProDOT-SO3Na + 80% ProDOT. Data are shown from cycle #50 after the behavior of each film stabilized.
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biosensors-02-00305-f003: Cyclic voltammetry data for functional ProDOT films electrochemically deposited from solutions of (A) 10% ProDOT-CO2H + 90% ProDOT and 20% ProDOT-CO2H + 80% ProDOT, (B) 10% ProDOT-NH2 + 90% ProDOT and 20% ProDOT-NH2 + 80% ProDOT, (C) 10% ProDOT-glycerol + 90% ProDOT and 20% ProDOT-glycerol + 80% ProDOT, and (D) 10% ProDOT-SO3Na + 90% ProDOT and 20% ProDOT-SO3Na + 80% ProDOT. Data are shown from cycle #50 after the behavior of each film stabilized.

Mentions: The electrochemically deposited films were characterized by cyclic voltammetry to demonstrate their conductivity and compare to pure ProDOT films. As seen in Figure 3, the oxidation and reduction potentials of the films containing functional monomer are not substantially changed as compared to ProDOT films, yet in all cases the electrochemical activity decreased with increasing comonomer in the feed solution. In the case of ProDOT-SO3Na, much of the film appeared to wash away upon electrochemical evaluation in aqueous solutions due to the high water solubility of the functional monomer. The decrease in electrical activity is likely due in part to the changes in film morphology seen by SEM (Figure 2). Although conductivity is maintained by functionalizing the side chain rather than the polymer backbone, the change in monomer solubility still affects the electrochemical properties of films in an indirect way.


Functional Conducting Polymers via Thiol-ene Chemistry.

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

Cyclic voltammetry data for functional ProDOT films electrochemically deposited from solutions of (A) 10% ProDOT-CO2H + 90% ProDOT and 20% ProDOT-CO2H + 80% ProDOT, (B) 10% ProDOT-NH2 + 90% ProDOT and 20% ProDOT-NH2 + 80% ProDOT, (C) 10% ProDOT-glycerol + 90% ProDOT and 20% ProDOT-glycerol + 80% ProDOT, and (D) 10% ProDOT-SO3Na + 90% ProDOT and 20% ProDOT-SO3Na + 80% ProDOT. Data are shown from cycle #50 after the behavior of each film stabilized.
© Copyright Policy - open-access
Related In: Results  -  Collection

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

biosensors-02-00305-f003: Cyclic voltammetry data for functional ProDOT films electrochemically deposited from solutions of (A) 10% ProDOT-CO2H + 90% ProDOT and 20% ProDOT-CO2H + 80% ProDOT, (B) 10% ProDOT-NH2 + 90% ProDOT and 20% ProDOT-NH2 + 80% ProDOT, (C) 10% ProDOT-glycerol + 90% ProDOT and 20% ProDOT-glycerol + 80% ProDOT, and (D) 10% ProDOT-SO3Na + 90% ProDOT and 20% ProDOT-SO3Na + 80% ProDOT. Data are shown from cycle #50 after the behavior of each film stabilized.
Mentions: The electrochemically deposited films were characterized by cyclic voltammetry to demonstrate their conductivity and compare to pure ProDOT films. As seen in Figure 3, the oxidation and reduction potentials of the films containing functional monomer are not substantially changed as compared to ProDOT films, yet in all cases the electrochemical activity decreased with increasing comonomer in the feed solution. In the case of ProDOT-SO3Na, much of the film appeared to wash away upon electrochemical evaluation in aqueous solutions due to the high water solubility of the functional monomer. The decrease in electrical activity is likely due in part to the changes in film morphology seen by SEM (Figure 2). Although conductivity is maintained by functionalizing the side chain rather than the polymer backbone, the change in monomer solubility still affects the electrochemical properties of films in an indirect way.

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.