Living cationic polymerization of an azide‐containing vinyl ether toward addressable functionalization of polymers |
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Authors: | Shohei Ida Makoto Ouchi Mitsuo Sawamoto |
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Institution: | Department of Polymer Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Kyoto 615‐8510, Japan |
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Abstract: | We first achieved the living cationic polymerization of azide‐containing monomer, 2‐azidoethyl vinyl ether (AzVE), with SnCl4 as a catalyst (activator) in conjunction with the HCl adduct of a vinyl ether H‐CH2CH(OR)‐Cl; R ? CH2CH2Cl, CH2CH(CH3)2]. Despite the potentially poisoning azide group, the produced polymers possessed controlled molecular weights and fairly narrow distributions (Mw/Mn ~ 1.2) and gave block polymers with 2‐chloroethyl vinyl ether. The pendent azide groups are easily converted into various functional groups via mild and selective reactions, such as the Staudinger reduction and copper‐catalyzed azide‐alkyne 1,3‐cycloaddition (CuAAC; a “click” reaction). These reactions led to quantitative pendent functionalization into primary amine (? NH2), hydroxy (? OH), and carboxyl (? COOH) groups, at room temperature and without any acidic or basic treatment. Thus, poly(AzVE) is a versatile precursor for a wide variety of functional vinyl ether polymers with well‐defined structures and molecular weights. © 2010 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 48: 1449–1455, 2010 |
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Keywords: | cationic polymerization click chemistry functionalization of polymers living polymerization vinyl ether |
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