Thiol-Michael coupling and ring-opening metathesis polymerization: Facile access to functional exo-7-oxanorbornene dendron macromonomers

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-epoxyi...

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Bibliographic Details
Main Authors: Liu, M., Burford, R., Lowe, Andrew
Format: Journal Article
Published: John Wiley and Sons Ltd 2014
Online Access:http://hdl.handle.net/20.500.11937/6395
Description
Summary: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 (ĐM = inline image w/ inline image n).