Vitamin C Loaded Polyethylene: Synthesis and Properties of Precise Polyethylene with Vitamin C Defects via Acyclic Diene Metathesis Polycondensation.

Oksana Suraeva,Ingo Lieberwirth,Volker Mailänder,Markus Mezger,Frederik R Wurm,Katharina Landfester,Rüdiger Berger,Carole Champanhac,Henning Weiss

doi:10.1021/acs.macromol.0c00086

Abstract

A polyethylene-like polymer with an in-chain vitamin C group was synthesized by olefin metathesis polymerization. Here, we describe both the synthesis and a comprehensive physical characterization. Because of the olefin metathesis synthesis, the vitamin C groups are equidistantly arranged in the polyethylene (PE) main chain. Their separation was adjusted to 20 CH2 units. After hydrogenation, a semicrystalline polymer is obtained that is soluble in polar solvents. Because of its size and steric effect, the vitamin C acts as a chain defect, which is expelled from the crystal lattice, yielding a lamellar crystal with a homogeneous thickness corresponding to the interdefect distance. The physical properties were examined by various methods including differential scanning calorimetry, X-ray scattering, and transmission electron microscopy. We show that vitamin C retains its radical scavenger properties despite being incorporated into a polyethylene chain. Furthermore, we demonstrate that it is degrading in alkaline conditions. To complete its suitability as a biocompatible material, cytotoxicity and cell uptake experiments were performed. We show that the polymer is nontoxic and that it is taken up in nanoparticular form via endocytosis processes into the cytoplasm of cells.

Highlights

The material class of polymers is characterized, among other things, by the fact that the properties and functionality of the material can be adjusted via the macromolecular architecture
The acetonide 2 crystallized directly from the reaction in yields of 80−85%. The speed of this reaction depends on the temperature: at 0 °C even after several hours stirring no changes were detected (Figure S1); after 4 h at room temperature the appearance of peaks at 4.06, 4.20, 4.49, and 4.81 ppm in the 1H NMR spectrum is indicative of acetonide
This work reports on the synthesis of a polyethylene-like polymer with a vitamin C group built into the main chain

Summary

Introduction

The material class of polymers is characterized, among other things, by the fact that the properties and functionality of the material can be adjusted via the macromolecular architecture. It is possible to design a polymer with a certain property or functionality This can be achieved by transferring the functionality of a specific molecule to the polymer during polymerization.[1−3]. The random defect distribution makes it difficult to estimate the influence of defects on the properties of the polymer. This applies to polymers that contain functional groups. In contrast to most other polymerizations, acyclic diene metathesis polymerization (ADMET) is characterized by the fact that the functional groups are integrated into the polymer chain at a precisely defined distance. Received: January 14, 2020 Revised: March 30, 2020 Published: April 8, 2020

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