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Authors
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Oehlenschleger, K. ; Guimard, N. ; Brandt, J. ; Müller, J. ; Lin, C. Y. ; Hilf, S. ; Lederer, A. ; Coote, M. ; Schmidt, F. G. ; Barner-Kowollik, C.
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Title
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Fast and catalyst-free hetero-diels-alder chemistry for on demand cyclable bonding/debonding materials
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Date
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23.05.2013
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Number
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38502
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Abstract
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A new dithioester possessing a cyano Z-group (cyano dtihioester (CDTE)) has been synthesized via a 2-step, one-pot reaction. The cyano-substituted dithioester has been found to undergo ultra fast reversible hetero-Diels-Alder (HDA) reactions at ambient temperature, without the need of a catalyst, as demonstrated by ESI-MS and UV-Vis experiments. To apply the bonding/debonding on demand system to material 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 and switching of the polymer systems was 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.
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Publisher
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Polymer Chemistry
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Wikidata
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Citation
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Polymer Chemistry 2013 (2013) 4348-4355
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DOI
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https://doi.org/10.1039/C3PY00476G
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Tags
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