title: Maleimide Glycidyl Ether: A Bifunctional Monomer for Orthogonal Cationic and Radical Polymerizations.
abstract: A novel bifunctional monomer, namely maleimide glycidyl ether (MalGE), prepared in a four-step reaction sequence is introduced. This monomer allows for selective (co)polymerization of the epoxide group via cationic ring-opening polymerization, preserving the maleimide functionality. On the other hand, the maleimide functionality can be copolymerized via radical techniques, preserving the epoxide moiety. Cationic ring-opening multibranching copolymerization of MalGE with glycidol was performed, and a MalGE content of up to 24 mol% could be incorporated into the hyperbranched polymer backbone (Mn = 1000-3000 g mol(-1)). Preservation of the maleimide functionality during cationic copolymerization was verified via NMR spectroscopy. Subsequently, the maleimide moiety was radically crosslinked to generate hydrogels and additionally employed to perform Diels-Alder (DA) "click" reactions with (functional) dienes after the polymerization process. Radical copolymerization of MalGE with styrene (Mn = 5000-9000 g mol(-1)) enabled the synthesis of a styrene copolymer with epoxide functionalities that are useful for versatile crosslinking and grafting reactions.
authors: Institute of Organic Chemistry, Johannes Gutenberg University Mainz, Duesbergweg 10-14, D-55128, Mainz, Germany.|Graduate School "Materials Science in Mainz", Staudingerweg 9, D-55128, Mainz, Germany.
authors: Rebecca
authors: R
authors: Klein
authors: Institute of Organic Chemistry, Johannes Gutenberg University Mainz, Duesbergweg 10-14, D-55128, Mainz, Germany.
authors: Fabian
authors: F
authors: Übel
authors: Institute of Organic Chemistry, Johannes Gutenberg University Mainz, Duesbergweg 10-14, D-55128, Mainz, Germany.
authors: Holger
authors: H
authors: Frey
mesh_terms: D002412:Cations; D004852:Epoxy Compounds / Q000737:chemistry; D004987:Ethers / Q000737:chemistry; D005609:Free Radicals / Q000737:chemistry; D008301:Maleimides / Q000737:chemistry*; D058105:Polymerization; D011108:Polymers / Q000138:chemical synthesis*; D020005:Propanols / Q000737:chemistry
chemical_list: D002412:Cations; D004852:Epoxy Compounds; D004987:Ethers; D005609:Free Radicals; D008301:Maleimides; D011108:Polymers; D020005:Propanols; C004312:glycidol
keywords: bifunctional; cationic polymerization; hyperbranched poly(glycerol); maleimide; radical polymerization