Repurposing Mitsunobu Reactions as a Generic Approach toward Polyethylene Derivatives.

Abstract

Broad scope of functionality and controllable degree of functionalization are intriguing goals for the development of polar-group-functionalized polyethylene materials. Herein, we propose a generic strategy of using widely available starting materials (i.e., poly(ethylene-co-vinyl acetate), EVA) and mild Mitsunobu functionalization conditions to prepare over 30 polyethylene derivatives. No noble transition metal catalysts (e.g., Ru, Mo, Pd, etc.) or corrosive/explosive reagents (e.g., HBr, NaN3, C2H4, H2, etc.) are used in the synthesis, while functional groups such as azide, aldehyde, norbornene, and thiol can be easily installed, with tunable content as high as 18 mol %. Using this practical method, we successfully prepared polyethylene-derivatized membranes with excellent antimicrobial and fluorescent properties.