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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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. © 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: mcoote@rsc.anu.edu.au
References: Billiet, S., Hillewaere, X.K.D., Teixeira, R.F.A., Du Prez, F.E., (2013) Macromol. Rapid Commun., 34, pp. 290-309; Guimard, N.K., Oehlenschlaeger, K.K., Zhou, J., Hilf, S., Schmidt, F.G., Barner-Kowollik, C., (2012) Macromol. Chem. Phys., 213, pp. 131-143; Sheridan, R.J., Bowman, C.N., (2013) Polym. Chem., , 10.1039/c1032py20960h; Paulöhrl, T., Inglis, A.J., Barner-Kowollik, C., (2010) Adv. Mater., 22, pp. 2788-2791; Zhou, J., Guimard, N.K., Inglis, A.J., Namazian, M., Lin, C.Y., Coote, M.L., Spyrou, E., Barner-Kowollik, C., (2012) Polym. Chem., 3, pp. 628-639; Chen, X., Wudl, F., Mal, A.K., Shen, H., Nutt, S.R., (2003) Macromolecules, 36, pp. 1802-1807; Kotha, S., Banerjee, S., Patil, M.P., Sunoj, R.B., (2006) Org. Biomol. Chem., 4, pp. 1854-1856; Amamoto, Y., Kamada, J., Otsuka, H., Takahara, A., Matyjaszewski, K., (2011) Angew. Chem., Int. Ed., 50, pp. 1660-1663; Froimowicz, P., Frey, H., Landfester, K., (2011) Macromol. Rapid Commun., 32, pp. 468-473; Deng, G., Tang, C., Li, F., Jiang, H., Chen, Y., (2010) Macromolecules, 43, pp. 1191-1194; Pepels, M., Filot, I.A.W., Klumperman, B., Goossens, H., (2013) Polym. Chem., , 10.1039/c3py00087g; Vogt, A.P., Sumerlin, B.S., (2009) Soft Matter, 5, pp. 2347-2351; Bai, N., Saito, K., Simon, G.P., (2013) Polym. Chem., 4, pp. 724-730; Gandini, A., Silvestre, A., Coelho, D., (2013) Polym. Chem., 4, pp. 1364-1371; Inglis, A.J., Nebhani, L., Altintas, O., Schmidt, F.G., Barner-Kowollik, C., (2010) Macromolecules, 43, pp. 5515-5520; Murphy, E.B., Bolanos, E., Schaffner-Hamann, C., Wudl, F., Nutt, S.R., Auad, M.L., (2008) Macromolecules, 41, pp. 5203-5209; Chen, X., Dam, M.A., Ono, K., Mal, A., Shen, H., Nutt, S.R., Sheran, K., Wudl, F., (2002) Science, 295, pp. 1698-1702; Zhang, Y., Broekhuis, A.A., Picchioni, F., (2009) Macromolecules, 42, pp. 1906-1912; Adzima, B.J., Kloxin, C.J., Bowman, C.N., (2010) Adv. Mater., 22, pp. 2784-2787; Wouters, M., Craenmehr, E., Tempelaars, K., Fischer, H., Stroeks, N., Van Zanten, J., (2009) Prog. Org. Coat., 64, pp. 156-162; Gandini, A., Belgacem, M.N., (1997) Prog. Polym. Sci., 22, pp. 1203-1379; Bowman, C.N., Kloxin, C.J., (2012) Angew. Chem., Int. Ed., 51, pp. 4272-4274; Syrett, J.A., Mantovani, G., Barton, W.R.S., Price, D., Haddleton, D.M., (2010) Polym. Chem., 1, pp. 102-106; Reutenauer, P., Buhler, E., Boul, P.J., Candau, S.J., Lehn, J.M., (2009) Chem.-Eur. J., 15, pp. 1893-1900; Glassner, M., Delaittre, G., Kaupp, M., Blinco, J.P., Barner-Kowollik, C., (2012) J. Am. Chem. Soc., 134, pp. 7274-7277; Sinnwell, S., Inglis, A.J., Davis, T.P., Stenzel, M.H., Barner-Kowollik, C., (2008) Chem. Commun., pp. 2052-2054; Vyas, D.M., Hay, G.W., (1971) J. Chem. Soc., Chem. Commun., pp. 1411-1412; Vyas, D.M., Hay, G.W., (1971) Can. J. Chem., 49, pp. 3755-3758; Vyas, D.M., Hay, G.W., (1975) J. Chem. Soc., Perkin Trans. 1, pp. 180-186; Bähr, G., Schleitzer, G., (1955) Chem. Ber., 88, pp. 1771-1777; Simmons, H.E., Blomstrom, D.C., Vest, R.D., (1962) J. Am. Chem. Soc., 84, pp. 4756-4771; Bähr, G., Schleitzer, G., (1957) Chem. Ber., 90, pp. 438-443; Maciejewski, A., Steer, R.P., (1993) Chem. Rev., 93, pp. 67-98; Gilchrist, T.L., Wood, J.E., (1992) J. Chem. Soc., Chem. Commun., pp. 1460-1461; Guimard, N.K., Ho, J., Brandt, J., Lin, C.Y., Namazian, M., Mueller, J.O., Oehlenschlaeger, K.K., Barner-Kowollik, C., (2013) Chem. Sci., , 10.1039/c3sc50642h
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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