Green polymer chemistry: living dithiol polymerization via cyclic intermediates.
Identifieur interne : 000905 ( Ncbi/Curation ); précédent : 000904; suivant : 000906Green polymer chemistry: living dithiol polymerization via cyclic intermediates.
Auteurs : Emily Q. Rosenthal [États-Unis] ; Judit E. Puskas ; Chrys WesdemiotisSource :
- Biomacromolecules [ 1526-4602 ] ; 2012.
Descripteurs français
- KwdFr :
- MESH :
- synthèse chimique : Polymères.
- Catalyse, Disulfures, Dithiothréitol, Oxydoréduction, Peroxyde d'hydrogène, Polymères, Thiols, Éthers éthyliques, Éthylamines.
English descriptors
- KwdEn :
- MESH :
- chemical , chemical synthesis : Polymers.
- chemical , chemistry : Disulfides, Dithiothreitol, Ethyl Ethers, Ethylamines, Hydrogen Peroxide, Polymers, Sulfhydryl Compounds.
- Catalysis, Oxidation-Reduction.
Abstract
This paper reports the synthesis and characterization of disulfide polymers obtained by oxidation of 2-[2-(2-sulfanylethoxy)ethoxy]ethanethiol (DODT) using a benign, synergistic system comprised of air, dilute hydrogen peroxide and triethylamine as a catalyst that can be recycled. The dn/dc value of the polymer in THF was determined to obtain absolute molecular weight measurements. High molecular weight disulfide polymers (up to M(n) = 250000 g/mol) with polydispersity indices as low as M(w)/M(n) = 1.15 were obtained. Thermal analysis by DSC and TGA demonstrated that the rubbery polymers had a T(g) of -50 °C and began to degrade at 250 °C. Dithiothreitol reduced the polymers back to the original monomeric units in 33 h. MALDI-ToF showed the involvement of oligodisulfide rings (2-14 mers) in the polymerization that displayed the characteristics of a living/controlled polymerization; poly(DODT) was readily chain extended with 1,2-ethanedithiol. The chain extension indicates a class of living polymerization which is governed by radical recombination.
DOI: 10.1021/bm201395t
PubMed: 22133097
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pubmed:22133097Le document en format XML
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<author><name sortKey="Wesdemiotis, Chrys" sort="Wesdemiotis, Chrys" uniqKey="Wesdemiotis C" first="Chrys" last="Wesdemiotis">Chrys Wesdemiotis</name>
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<series><title level="j">Biomacromolecules</title>
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<term>Dithiothreitol (chemistry)</term>
<term>Ethyl Ethers (chemistry)</term>
<term>Ethylamines (chemistry)</term>
<term>Hydrogen Peroxide (chemistry)</term>
<term>Oxidation-Reduction</term>
<term>Polymers (chemical synthesis)</term>
<term>Polymers (chemistry)</term>
<term>Sulfhydryl Compounds (chemistry)</term>
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<keywords scheme="KwdFr" xml:lang="fr"><term>Catalyse</term>
<term>Disulfures ()</term>
<term>Dithiothréitol ()</term>
<term>Oxydoréduction</term>
<term>Peroxyde d'hydrogène ()</term>
<term>Polymères ()</term>
<term>Polymères (synthèse chimique)</term>
<term>Thiols ()</term>
<term>Éthers éthyliques ()</term>
<term>Éthylamines ()</term>
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<keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Polymers</term>
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<term>Dithiothreitol</term>
<term>Ethyl Ethers</term>
<term>Ethylamines</term>
<term>Hydrogen Peroxide</term>
<term>Polymers</term>
<term>Sulfhydryl Compounds</term>
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<term>Disulfures</term>
<term>Dithiothréitol</term>
<term>Oxydoréduction</term>
<term>Peroxyde d'hydrogène</term>
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<term>Thiols</term>
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<term>Éthylamines</term>
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<front><div type="abstract" xml:lang="en">This paper reports the synthesis and characterization of disulfide polymers obtained by oxidation of 2-[2-(2-sulfanylethoxy)ethoxy]ethanethiol (DODT) using a benign, synergistic system comprised of air, dilute hydrogen peroxide and triethylamine as a catalyst that can be recycled. The dn/dc value of the polymer in THF was determined to obtain absolute molecular weight measurements. High molecular weight disulfide polymers (up to M(n) = 250000 g/mol) with polydispersity indices as low as M(w)/M(n) = 1.15 were obtained. Thermal analysis by DSC and TGA demonstrated that the rubbery polymers had a T(g) of -50 °C and began to degrade at 250 °C. Dithiothreitol reduced the polymers back to the original monomeric units in 33 h. MALDI-ToF showed the involvement of oligodisulfide rings (2-14 mers) in the polymerization that displayed the characteristics of a living/controlled polymerization; poly(DODT) was readily chain extended with 1,2-ethanedithiol. The chain extension indicates a class of living polymerization which is governed by radical recombination.</div>
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