Issue 19, 2016

A mild, efficient and catalyst-free thermoreversible ligation system based on dithiooxalates

Abstract

We demonstrate a novel and ready to prepare thermoreversible hetero Diels–Alder dilinker on the basis of dithiooxalates, enabling the mild, rapid and catalyst-free linkage of diverse diene species under ambient conditions for applications in the fields of, for example, modular ligation, self-healing or recyclable materials and surface modification amongst others. The linker was studied using quantum chemical calculations, and experimentally in small molecular reactions via UV/Vis spectroscopy, mass spectrometry and NMR as well as in step-growth polymerizations with diene-difunctional building blocks – characterized via (temperature dependent) SEC and HT NMR – as an example for efficient polymer ligation.

Graphical abstract: A mild, efficient and catalyst-free thermoreversible ligation system based on dithiooxalates

Supplementary files

Article information

Article type
Paper
Submitted
16 Mar 2016
Accepted
14 Apr 2016
First published
14 Apr 2016

Polym. Chem., 2016,7, 3244-3250

A mild, efficient and catalyst-free thermoreversible ligation system based on dithiooxalates

K. Pahnke, N. L. Haworth, J. Brandt, U. Paulmann, C. Richter, F. G. Schmidt, A. Lederer, M. L. Coote and C. Barner-Kowollik, Polym. Chem., 2016, 7, 3244 DOI: 10.1039/C6PY00470A

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