Fast and catalyst-free hetero-diels-alder chemistry for on demand cyclable bonding/debonding materials

Kim K. Oehlenschlaeger, Nathalie K. Guimard, Josef Brandt, Jan O. Mueller, Ching Yeh Lin, Stefan Hilf, Albena Lederer, Michelle L. Coote, Friedrich G. Schmidt, Christopher Barner-Kowollik

Research output: Contribution to journalArticlepeer-review

52 Citations (Scopus)

Abstract

A new dithioester possessing a cyano Z-group (cyano-dithioester (CDTE)) has been synthesized via a 2-step, one-pot reaction. The cyano-substituted dithioester has been found to undergo fast reversible hetero-Diels-Alder (HDA) reactions at ambient temperature, without the need for a catalyst, as demonstrated by ESI-MS and UV-Vis experiments. To apply the bonding/debonding on demand system to materials science, a cyano-dithioester di-linker was synthesized and employed as a di-functional dienophile in a HDA-based polymerization reaction with a bis-cyclopentadiene polymer. The reversible bonding of the polymer systems were demonstrated by on-line UV-Vis spectroscopy, on-line NMR spectroscopy, and on-line high temperature DLS, as well as via GPC in situ trapping experiments and high-level ab initio molecular orbital calculations.

Original languageEnglish
Pages (from-to)4348-4355
Number of pages8
JournalPolymer Chemistry
Volume4
Issue number16
DOIs
Publication statusPublished - 21 Aug 2013
Externally publishedYes

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