Thiol‐Michael coupling and ring‐opening metathesis polymerization: facile access to functional exo‐7‐oxanorbornene dendron macromonomers |
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Authors: | Meina Liu Robert P Burford Andrew B Lowe |
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Affiliation: | Centre for Advanced Macromolecular Design (CAMD), School of Chemical Engineering, University of New South Wales, , Kensington, Sydney, NSW 2052 Australia |
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Abstract: | This paper describes the synthesis of the 2‐ and 4‐functional acrylic exo‐7‐oxanorbornene species 2‐((2‐((3aR,7aS)‐1,3‐dioxo‐1,3,3a,4,7,7a‐hexahydro‐2H‐4,7‐epoxyisoindol‐2‐yl)ethoxy) carbonyl)‐2‐methylpropane‐1,3‐diyl diacrylate and (((2‐((2‐((3aR,7aS)‐1,3‐dioxo‐1,3,3a,4,7,7a‐hexahydro‐2H‐4,7‐epoxyisoindol‐2‐yl)ethoxy) carbonyl)‐2‐methylpropane‐1,3‐diyl)bis(oxy))bis(carbonyl))bis(2‐methylpropane‐2,1,3‐triyl) tetraacrylate, and their use as common precursors for the preparation of a small library of dendronized thioether adducts via nucleophile‐mediated thiol‐Michael coupling chemistry. We subsequently demonstrate that the dendronized monomers can be (co)polymerized via ring‐opening metathesis polymerization employing Grubbs'‐type Ru‐based initiators to give novel functional dendronized (co)polymers of predictable molecular weights and acceptable dispersities (?M = w/ n). © 2013 Society of Chemical Industry |
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Keywords: | ROMP dendrons dendronized polymers thiol‐Michael click |
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