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Issue 16, 2013
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Fast and catalyst-free hetero-Diels–Alder chemistry for on demand cyclable bonding/debonding materials

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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.

Graphical abstract: Fast and catalyst-free hetero-Diels–Alder chemistry for on demand cyclable bonding/debonding materials

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Supplementary files

Article information


Submitted
14 Apr 2013
Accepted
21 May 2013
First published
23 May 2013

Polym. Chem., 2013,4, 4348-4355
Article type
Paper

Fast and catalyst-free hetero-Diels–Alder chemistry for on demand cyclable bonding/debonding materials

K. K. Oehlenschlaeger, N. K. Guimard, J. Brandt, J. O. Mueller, C. Y. Lin, S. Hilf, A. Lederer, M. L. Coote, F. G. Schmidt and C. Barner-Kowollik, Polym. Chem., 2013, 4, 4348
DOI: 10.1039/C3PY00476G

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