Green polymer chemistry: living dithiol polymerization via cyclic intermediates.
Identifieur interne : 002252 ( Main/Exploration ); précédent : 002251; suivant : 002253Green 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
Affiliations:
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Puskas</name></author><author><name sortKey="Wesdemiotis, Chrys" sort="Wesdemiotis, Chrys" uniqKey="Wesdemiotis C" first="Chrys" last="Wesdemiotis">Chrys Wesdemiotis</name></author></titleStmt><publicationStmt><idno type="wicri:source">PubMed</idno><date when="2012">2012</date><idno type="RBID">pubmed:22133097</idno><idno type="pmid">22133097</idno><idno type="doi">10.1021/bm201395t</idno><idno type="wicri:Area/PubMed/Corpus">001E31</idno><idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Corpus" wicri:corpus="PubMed">001E31</idno><idno type="wicri:Area/PubMed/Curation">001E31</idno><idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Curation">001E31</idno><idno type="wicri:Area/PubMed/Checkpoint">001C79</idno><idno type="wicri:explorRef" wicri:stream="Checkpoint" wicri:step="PubMed">001C79</idno><idno type="wicri:Area/Ncbi/Merge">000905</idno><idno type="wicri:Area/Ncbi/Curation">000905</idno><idno type="wicri:Area/Ncbi/Checkpoint">000905</idno><idno type="wicri:Area/Main/Merge">002277</idno><idno type="wicri:Area/Main/Curation">002252</idno><idno type="wicri:Area/Main/Exploration">002252</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en">Green polymer chemistry: living dithiol polymerization via cyclic intermediates.</title><author><name sortKey="Rosenthal, Emily Q" sort="Rosenthal, Emily Q" uniqKey="Rosenthal E" first="Emily Q" last="Rosenthal">Emily Q. Rosenthal</name><affiliation wicri:level="1"><nlm:affiliation>Department of Polymer Science, The University of Akron, Akron, Ohio 44325, United States.</nlm:affiliation><country xml:lang="fr">États-Unis</country><wicri:regionArea>Department of Polymer Science, The University of Akron, Akron, Ohio 44325</wicri:regionArea><wicri:noRegion>Ohio 44325</wicri:noRegion></affiliation></author><author><name sortKey="Puskas, Judit E" sort="Puskas, Judit E" uniqKey="Puskas J" first="Judit E" last="Puskas">Judit E. Puskas</name></author><author><name sortKey="Wesdemiotis, Chrys" sort="Wesdemiotis, Chrys" uniqKey="Wesdemiotis C" first="Chrys" last="Wesdemiotis">Chrys Wesdemiotis</name></author></analytic><series><title level="j">Biomacromolecules</title><idno type="eISSN">1526-4602</idno><imprint><date when="2012" type="published">2012</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Catalysis</term><term>Disulfides (chemistry)</term><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></keywords><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></keywords><keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Polymers</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Disulfides</term><term>Dithiothreitol</term><term>Ethyl Ethers</term><term>Ethylamines</term><term>Hydrogen Peroxide</term><term>Polymers</term><term>Sulfhydryl Compounds</term></keywords><keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>Polymères</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Catalysis</term><term>Oxidation-Reduction</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Catalyse</term><term>Disulfures</term><term>Dithiothréitol</term><term>Oxydoréduction</term><term>Peroxyde d'hydrogène</term><term>Polymères</term><term>Thiols</term><term>Éthers éthyliques</term><term>Éthylamines</term></keywords></textClass></profileDesc></teiHeader><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></front></TEI><affiliations><list><country><li>États-Unis</li></country></list><tree><noCountry><name sortKey="Puskas, Judit E" sort="Puskas, Judit E" uniqKey="Puskas J" first="Judit E" last="Puskas">Judit E. Puskas</name><name sortKey="Wesdemiotis, Chrys" sort="Wesdemiotis, Chrys" uniqKey="Wesdemiotis C" first="Chrys" last="Wesdemiotis">Chrys Wesdemiotis</name></noCountry><country name="États-Unis"><noRegion><name sortKey="Rosenthal, Emily Q" sort="Rosenthal, Emily Q" uniqKey="Rosenthal E" first="Emily Q" last="Rosenthal">Emily Q. Rosenthal</name></noRegion></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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