Access to Multiblock Copolymers via Supramolecular Host-Guest Chemistry and Photochemical Ligation

Hirschbiel, A. F., Konrad, W., Schulze-Sünninghausen, D., Wiedmann, S., Luy, B., Schmidt, B. V. K. J., & Barner-Kowollik, C. (2015) Access to Multiblock Copolymers via Supramolecular Host-Guest Chemistry and Photochemical Ligation. ACS Macro Letters, 4(10).

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We combine supramolecular host-guest interactions of β-cyclodextrin (CD) with light-induced Diels-Alder reactions of 2-methoxy-6-methylbenzaldehyde (photoenol, PE) for the formation of multiblock copolymers. Via the synthesis of a new bifunctional chain transfer agent (CTA) and subsequent reversible addition-fragmentation chain transfer (RAFT) polymerization, we introduce a supramolecular recognition unit (tert-butyl phenyl) and a photoactive unit (photoenol) to a polymer chain in order to obtain an α,ω-functionalized polymeric center block, having orthogonal recognition units at each chain end. Multiblock copolymers are formed via the light-induced reaction of the photoenol with a maleimide-functionalized polymer chain and the supramolecular self-assembly of the tert-butyl phenyl group with the β-CD end group of a third polymer chain. By employing the fast and efficient photoinduced Diels-Alder reaction in combination with supramolecular host-guest interactions, a novel method for macromolecular modular ligation is introduced. © 2015 American Chemical Society.

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ID Code: 99432
Item Type: Journal Article
Refereed: Yes
Additional Information: Cited By :3 Export Date: 5 September 2016 Correspondence Address: Schmidt, B.V.K.J.; Max Planck Institute of Colloids and InterfacesGermany References: Johnson, J.A., Finn, M.G., Koberstein, J.T., Turro, N.J., (2008) Macromol. Rapid Commun., 29 (1213), pp. 1052-1072; Durmaz, H., Sanyal, A., Hizal, G., Tunca, U., (2012) Polym. Chem., 3 (4), pp. 825-835; Bosman, A.W., Vestberg, R., Heumann, A., Fréchet, J.M.J., Hawker, C.J., (2003) J. Am. Chem. Soc., 125 (3), pp. 715-728; Glassner, M., Oehlenschlaeger, K.K., Gruendling, T., Barner-Kowollik, C., (2011) Macromolecules, 44 (12), pp. 4681-4689; Du, A.W., Stenzel, M.H., (2014) Biomacromolecules, 15 (4), pp. 1097-1114; Peng, L., Feng, A., Zhang, H., Wang, H., Jian, C., Liu, B., Gao, W., Yuan, J., (2014) Polym. Chem., 5 (5), pp. 1751-1759; Van Nostrum, C.F., (2011) Soft Matter, 7 (7), pp. 3246-3259; Liu, B.-W., Zhou, H., Zhou, S.-T., Zhang, H.-J., Feng, A.-C., Jiam, C.-M., Hu, J., Uuan, J.-Y., (2014) Macromolecules, 47 (9), pp. 2938-2946; Hawker, C.J., Wooley, K.L., (2005) Science, 309 (5738), pp. 1200-1205; Sumerlin, B.S., Vogt, A.P., (2010) Macromolecules, 43 (1), pp. 1-13; Kempe, K., Krieg, A., Becer, C.R., Schubert, U.S., (2012) Chem. Soc. Rev., 41 (1), pp. 176-191; Inglis, A.J., Barner-Kowollik, C., (2010) Macromol. Rapid Commun., 31 (14), pp. 1247-1266; Chong, Y.K., Le, T.P.T., Moad, G., Rizzardo, E., Thang, S.H., (1999) Macromolecules, 32 (6), pp. 2071-2074; Oehlenschlaeger, K.K., Mueller, J.O., Heine, N.B., Glassner, M., Guimard, N.K., Delaittre, G., Schmidt, F.G., Barner-Kowollik, C., (2013) Angew. Chem., Int. Ed., 52 (2), pp. 762-766; Kaupp, M., Tischer, T., Hirschbiel, A.F., Vogt, A.P., Geckle, U., Trouillet, V., Hofe, T., Barner-Kowollik, C., (2013) Macromolecules, 46 (17), pp. 6858-6872; Tasdelen, M.A., Yagci, Y., (2013) Angew. Chem., Int. Ed., 52 (23), pp. 5930-5938; Chatani, S., Kloxin, C.J., Bowman, C.N., (2014) Polym. Chem., 5 (7), pp. 2187-2201; Schmidt, B.V.K.J., Hetzer, M., Ritter, H., Barner-Kowollik, C., (2014) Prog. Polym. Sci., 39 (1), pp. 235-249; Schmidt, B.V.K.J., Hetzer, M., Ritter, H., Barner-Kowollik, C., (2013) Macromolecules, 46 (3), pp. 1054-1065; Harada, A., Takashima, Y., Nakahata, M., (2014) Acc. Chem. Res., 47 (7), pp. 2128-2140; Stadermann, J., Komber, H., Erber, M., Däbritz, F., Ritter, H., Voit, B., (2011) Macromolecules, 44 (9), pp. 3250-3259; Yan, Q., Zhang, H., Zhao, Y., (2014) ACS Macro Lett., 3 (5), pp. 472-476; Zeng, J., Shi, K., Zhang, Y., Sun, X., Zhang, B., (2008) Chem. Commun., 32, pp. 3753-3755; Hirschbiel, A.F., Schmidt, B.V.K.J., Krolla-Sidenstein, P., Blinco, J.P., Barner-Kowollik, C., (2015) Macromolecules, 48 (13), pp. 4410-4420; Weickenmeier, M., Wenz, G., Huff, J., (1997) Macromol. Rapid Commun., 18 (12), pp. 1117-1123; Schmidt, B.V.K.J., Hetzer, M., Ritter, H., Barner-Kowollik, C., (2011) Macromolecules, 44 (18), pp. 7220-7232; Skey, J., O'Reilly, R.K., (2008) Chem. Commun., 35, pp. 4183-4185; Bays, E., Tao, L., Chang, C.-W., Maynard, H.D., (2009) Biomacromolecules, 10 (7), pp. 1777-1781; Li, X., Prukop, S.L., Biswal, S.L., Verduzco, R., (2012) Macromolecules, 45 (17), pp. 7118-7127; Nyström, F., Soeriyadi, A.H., Boyer, C., Zetterlund, P.B., Whittaker, M.R., (2011) J. Polym. Sci., Part A: Polym. Chem., 49 (24), pp. 5313-5321; Schmidt, B.V.K.J., Barner-Kowollik, C., (2014) ChemCatChem, 6 (11), pp. 3060-3062; Hiltebrandt, K., Pauloehrl, T., Blinco, J.P., Linkert, K., Börner, H.G., Barner-Kowollik, C., (2015) Angew. Chem., Int. Ed., 54 (9), pp. 2838-2843; Yan, Q., Xin, Y., Zhou, R., Yin, Y., Yuan, J., (2011) Chem. Commun., 47 (34), pp. 9594-9596; Szillat, F., Schmidt, B.V.K.J., Hubert, A., Barner-Kowollik, C., Ritter, H., (2014) Macromol. Rapid Commun., 35 (14), pp. 1293-1300; Zhang, Z., Lv, Q., Gao, X., Chen, L., Cao, Y., Yu, S., He, C., Chen, X., (2015) ACS Appl. Mater. Interfaces, 7 (16), pp. 8404-8411; Schmidt, B.V.K.J., Barner-Kowollik, C., (2014) Polym. Chem., 5 (7), pp. 2461-2472
DOI: 10.1021/acsmacrolett.5b00485
ISSN: 21611653
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: 27 Sep 2016 01:41

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