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Entropy‐Driven Ring‐Opening Disulfide Metathesis Polymerization for the Synthesis of Functional Poly(disulfide)s
Author(s) -
Behrendt Felix N.,
Schlaad Helmut
Publication year - 2018
Publication title -
macromolecular rapid communications
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.348
H-Index - 154
eISSN - 1521-3927
pISSN - 1022-1336
DOI - 10.1002/marc.201700735
Subject(s) - polymer chemistry , polymerization , monomer , metathesis , alkene , chemistry , polymer , ring opening polymerization , copolymer , dimethylacetamide , chain transfer , radical polymerization , organic chemistry , catalysis , solvent
Metal‐free entropy‐driven disulfide metathesis polymerization of unsaturated l ‐cystine based macrocycles produces high‐molar‐mass heterofunctional poly(disulfide)s, i.e., poly(ester‐disulfide‐alkene) and poly(amide‐disulfide‐alkene); M w app = 44–60 kDa, Ð > 1.7. The polymerization is fast and reaches equilibrium within 1–5 minutes (monomer conversion 70–90%) in polar aprotic solvents such as N,N ‐dimethylacetamide, dimethylsulfoxide, or γ‐valerolactone. Thiol‐terminated polymers are stable in bulk or when dissolved in weakly polar solvents, but rapidly depolymerize in dilute polar solution.