A Reductive Deuteration Approach to the Efficient Synthesis of Deuterated Polymers

Abstract

Deuterated polymers have wild applications but limited synthetic methods. In this study, we report an efficient two-step approach for the synthesis of deuterated polyesters and polyurethanes. Firstly, two practical single electron transfer (SET) reductive deuteration methods have been developed for site-selective introduction of C(sp3)–D into diol monomers. 9 deuterated diol monomers with high deuterium incorporations were synthesized under SmI2-D2O and/or Na-EtOD-d 1 SET reductive deuteration conditions. Then, 6 typical deuterated polyesters and polyurethanes were synthesized using those deuterated monomers under typical polymerization conditions. In all the synthesized polymers, high deuterium incorporation was fully maintained, which showcased the potential application of this approach for the synthesis of polymers with site-specific deuterium labelling.

Single Electron Transfer Reductive Deuteration of Acyl Chlorides for the Synthesis of Deuterated Alcohols with a High Deuterium Atom Economy

“…This demonstrates the potential of this protocol in the synthesis of multi-deuterium-labeled agrochemicals, drugs, and mass spectrometry (MS) internal standards. It is worth noting that deuterated diol 2r also serves as a useful monomer for the synthesis of valuable deuterated polymers, such as deuterated polyesters and polyurethanes …”