Green polymer chemistry: living dithiol polymerization via cyclic intermediates.
Identifieur interne : 000905 ( Ncbi/Merge ); 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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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. 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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><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">22133097</PMID><DateCompleted><Year>2012</Year><Month>04</Month><Day>24</Day></DateCompleted><DateRevised><Year>2013</Year><Month>11</Month><Day>21</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1526-4602</ISSN><JournalIssue CitedMedium="Internet"><Volume>13</Volume><Issue>1</Issue><PubDate><Year>2012</Year><Month>Jan</Month><Day>09</Day></PubDate></JournalIssue><Title>Biomacromolecules</Title><ISOAbbreviation>Biomacromolecules</ISOAbbreviation></Journal><ArticleTitle>Green polymer chemistry: living dithiol polymerization via cyclic intermediates.</ArticleTitle><Pagination><MedlinePgn>154-64</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1021/bm201395t</ELocationID><Abstract><AbstractText>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. 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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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