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.
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C. B.-K., M. L. C. and A. L. are grateful for continued support from and the excellent collaboration with Evonik Industries. C. B.-K. additionally acknowledges continued support from the KIT via the Helmholtz association (BIFTM and STN programs) as well as the German Research Council (DFG). M. L. C. acknowledges generous allocations of supercomputing time on the National Facility of the National Computational Infrastructure. The authors thank K. K. Oehlenschlaeger for fruitful discussions and J. Lenz for his help with the TD SEC characterization. K. P. acknowledges financial support from the Karlsruhe House of Young Scientists (KHYS) funding a research stay in the laboratories of M. L. C.
© The Royal Society of Chemistry 2016.