Amide-Functionalized Polyolefins and Facile Post-Transformations

Direct copolymerization of olefins with polar monomers to produce functionalized polyolefins has attracted much attention; however, highly efficient incorporation of amide functions into polyolefins is a long-standing challenge because the amide function is pronounced to retard chain growth. In this that contain high ring strain and an amide moiety are utilized in ethylene copolymerization mediated by palladium catalysts. Amidefunctionalized polyethylenes, poly(E-VLBoc)s, are accessible with key characteristics of high amide incorporations (up to 30.1 mol %), high copolymer molecular weights, and high catalytic activities. The incorporation of the amide comonomer converts crystalline poly(E-VLBoc)s (T-m = 115-125 degrees C) to noncrystalline and transparent poly(E-VLBoc)s (T-g = 98-196 degrees C, optical transmittance (T) = 87.6%-90.4%). Both characteristics of cyclic amide functions and high amide incorporations in poly(E-VLBoc) enable facile post-transformations under mild conditions to produce hydrogen bond-containing (-C(O)NH-) poly(E-VLH), difunctionalized (-COOH and -NHR) poly(E-VLNHBoc), and water-soluble ammonium-functionalized poly(E-VLNH3+). The ammonium functionality endows polyolefin with antibacterial properties.

Automated summary

The direct copolymerization of olefins with polar monomers to produce functionalized polyolefins, particularly those with amide functions, has been a challenge. However, by utilizing compounds with high ring strain and an amide moiety in ethylene copolymerization, high amide incorporation, molecular weights, and catalytic activities can be achieved. The resulting amide-functionalized polyethylenes can undergo facile post-transformations to produce polyethylenes with diverse functionalities, such as hydrogen bond-containing, difunctionalized, and water-soluble ammonium-functionalized polyethylenes, which exhibit antibacterial properties.