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

Oehlenschlaeger, K. K., Guimard, N. K., Brandt, J., Mueller, J. O., Lin, C. Y., Hilf, S., Lederer, A., Coote, M. L., Schmidt, F. G., & Barner-Kowollik, C. (2013) Fast and catalyst-free hetero-diels-alder chemistry for on demand cyclable bonding/debonding materials. Polymer Chemistry, 4(16).

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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. © 2013 The Royal Society of Chemistry.

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ID Code: 99356
Item Type: Journal Article
Refereed: Yes
Additional Information: Cited By :17
Export Date: 5 September 2016
Correspondence Address: Coote, M.L.; ARC Centre of Excellence for Free-Radical Chemistry and Biotechnology, Research School of Chemistry, Australian National University, Canberra, ACT 0200, Australia; email:
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Keywords: Ab initio molecular orbital calculation, Hetero-diels-Alder, On-demand systems, On-line NMR spectroscopy, One-pot reaction, Polymerization reaction, Reversible bonding, UV-vis spectroscopy, Calculations, Catalysts, Directive antennas, Experiments, Nuclear magnetic resonance spectroscopy, Orbital calculations, Ultraviolet visible spectroscopy, Organic polymers
DOI: 10.1039/c3py00476g
ISSN: 17599954
Divisions: Current > Schools > School of Chemistry, Physics & Mechanical Engineering
Current > Institutes > Institute for Future Environments
Current > QUT Faculties and Divisions > Science & Engineering Faculty
Deposited On: 22 Sep 2016 04:50
Last Modified: 29 Sep 2016 23:52

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