Reversible crosslinking of polymers bearing pendant or terminal thiol groups prepared by nitroxide-mediated radical polymerization

Intramolecular Cross-Linking Methodologies for the Synthesis of Polymer Nanoparticles

“…203 The authors synthesized several styreneand acrylate-based copolymers bearing protected thiol groups by nitroxide-mediated radical polymerization (NMRP). Thiol deprotection followed by oxidation upon exposure to air resulted mainly in cross-linked networks via disulfide formation.…”

Synthesis of sulfur-containing alternating copolymers by RAFT copolymerization of phenyl vinyl sulfides

“…The design of sulfur-containing polymers from functional vinyl monomers is a promising platform for providing new functional materials and unique optical polymers [15,16]. Controlled radical polymerizations of sulfur-containing vinyl monomers, such as pyridyl disulfide ethyl methacrylate [17][18][19][20], disulfide-based di(meth)acrylates [21][22][23][24], and vinyl monomers with protected thiol groups [25][26][27][28], have been employed in the production of a variety of functional polymers with well-defined structures and highly ordered architectures.…”

Protected thiol strategies in macromolecular design

“…It is also possible to build in redox-cleavable sites in the polymer backbone through disulfidecontaining monomers or cross-linkers [86,[116][117][118][119][120]. In contrast to pendant disulfide bonds, the cleavage of disulfide bonds incorporated in the polymer backbone results in the (partial or total) degradation of the polymer (network).…”

“…The thiols were recovered by reaction with TFA, after which they were converted in S-nitrosothiols, to serve as nitric oxide-releasing materials. Other examples include the synthesis of a trityl protected thiol polycarbonate [153] and the controlled radical polymerization (via NMP) of a styrenic trityl protected thiol [118].…”

“…After the polymerization, deprotection and subsequent modification reactions could be performed. The same strategy was applied to prepare polymers with protected thiols in their side-chains [118]. Vinyl benzyl chloride was transformed into a benzylic thiol in a two-step synthesis, again using thiourea as the source of sulfur (Scheme 29).…”