ATRP from a norbornenyl-functionalized initiator: Balancing of complementary reactivity for the preparation of alpha-norbornenyl macromonomers/omega-haloalkyl macroinitiators
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abstract
Atom transfer radical polymerization (ATRP) using a norbornenyl- functionalized initiator was established as a new synthetic method for the preparation of macromolecules that are both -norbornenyl macromonomers and -haloalkyl macroinitiators. When styrene, methyl methacrylate, and tert-butyl methacrylate were used as monomer or constituted comonomer pairs, the (co)polymerization was well-controlled and the norbornenyl functionality was intact. The resulting homopolymer or statistical copolymer-based macromonomers had linear structures, quantitative -norbornenyl functionality, controlled number-average molecular weights (M n = 3600-24300 Da), and narrow monomodal molecular weight distributions (M w/M n = 1.07-1.35). Their -halide terminals further allowed them to serve as macroinitiators for the syntheses of block copolymer-based -norbornenyl macromonomers by ATRP. In contrast, the norbornenyl functionality exhibited considerable competitive reactivity in the polymerizations of methyl acrylate and tert-butyl acrylate, resulting in mixed linear and branched macromonomers/macroinitiators. TGA analysis of -norbornenyl macromonomers showed that the presence of norbornenyl functionality appreciably enhanced their thermal stability. 2005 American Chemical Society.
