Journal
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Volume 10, Issue -, Pages 680-691Publisher
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.10.61
Keywords
chain-transfer polymerization; cyclodextrins; end-group functionalization; host-guest interaction; lower critical solution temperature (LCST); poly(N,N-diethylacrylamide)
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In this work we report the synthesis of thermo-, oxidation-and cyclodextrin-(CD) responsive end-group-functionalized polymers, based on N,N-diethylacrylamide (DEAAm). In a classical free-radical chain transfer polymerization, using thiol-functionalized 4-alkylphenols, namely 3-(4-(1,1-dimethylethan-1-yl)phenoxy)propane-1-thiol and 3-(4-(2,4,4-trimethylpentan-2-yl)phenoxy)propane-1-thiol, poly(N,N-diethylacrylamide) (PDEAAm) with well-defined hydrophobic end-groups is obtained. These end-group-functionalized polymers show different cloud point values, depending on the degree of polymerization and the presence of randomly methylated beta-cyclodextrin (RAMEB-CD). Additionally, the influence of the oxidation of the incorporated thioether linkages on the cloud point is investigated. The resulting hydrophilic sulfoxides show higher cloud point values for the lower critical solution temperature (LCST). A high degree of functionalization is supported by H-1 NMR-, SEC-, FTIR- and MALDI-TOF measurements.
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