A mild and efficient approach to functional single-chain polymeric nanoparticles via photoinduced Diels-Alder ligation

Altintas, O., Willenbacher, J., Wuest, K. N. R., Oehlenschlaeger, K. K., Krolla-Sidenstein, P., Gliemann, H., & Barner-Kowollik, C. (2013) A mild and efficient approach to functional single-chain polymeric nanoparticles via photoinduced Diels-Alder ligation. Macromolecules, 46(20).

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Abstract

We present a new ambient temperature synthetic approach for the preparation of single-chain polymeric nanoparticles (SCNPs) under mild conditions using a UV-light-triggered Diels-Alder (DA) reaction for the intramolecular cross-linking of single polymer chains. Well-defined random copolymers with varying contents of styrene (S) and 4-chloromethylstyrene (CMS) were synthesized employing a nitroxide-mediated radical polymerization (NMP) initiator functionalized with a terminal alkyne moiety. Postpolymerization modification with 4-hydroxy-2,5-dimethylbenzophenone (DMBP) and an N-maleimide (Mal) derivative led to the functional linear precursor copolymers. The intramolecular cross-linking was performed by activating the DMBP groups via irradiation with UV light of 320 nm for 30 min in diluted solution (cPolymer = 0.017 mg mL-1). The ensuing DA reaction between the activated DMBP and the Mal groups resulted in well-defined single-chain polymeric nanoparticles. To control the size of the SCNPs, random copolymers with varying CMS contents (i.e., different functional group densities (FGD)) were employed for the single-chain collapse. Additionally, monotethered nanoparticles were prepared via the copper-catalyzed azide-alkyne cycloaddition between the alkyne bearing copolymer with the highest FGD and an azide-terminated poly(ethylene glycol) (PEG) prior to UV-induced cross-linking. The formation of SCNPs was followed by size exclusion chromatography (SEC), nuclear magnetic resonance (NMR) spectroscopy, dynamic light scattering (DLS), and atomic force microscopy (AFM). © 2013 American Chemical Society.

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ID Code: 99337
Item Type: Journal Article
Refereed: Yes
Additional Information: Cited By :37
Export Date: 5 September 2016
CODEN: MAMOB
Correspondence Address: Barner-Kowollik, C.; Preparative Macromolecular Chemistry, Institut für Technische Chemie und Polymerchemie, Karlsruhe Institute of Technology (KIT), Engesserstr. 18, 76128 Karlsruhe, Germany; email: christopher.barner-kowollik@kit.edu
References: Caruso, F., Hyeon, T., Rotello, V., (2012) Chem. Soc. Rev., 41, pp. 2545-2561; Rao, J.P., Geckeler, K.E., (2011) Prog. Polym. Sci., 36, pp. 887-913; Sanchez-Sanchez, A., Pérez-Baena, I., Pomposo, J.A., (2013) Molecules, 18, pp. 3339-3355; Jackson, A.W., Fulton, D.A., (2013) Polym. Chem., 4, pp. 31-45; Altintas, O., Barner-Kowollik, C., (2012) Macromol. Rapid Commun., 33, pp. 958-971; Aiertza, M., Odriozola, I., Cabañero, G., Grande, H.-J., Loinaz, I., (2012) Cell. Mol. Life Sci., 69, pp. 337-346; Ouchi, M., Badi, N., Lutz, J.F., Sawamoto, M., (2011) Nat. Chem., 3, pp. 917-924; Chao, D., Jia, X., Tuten, B., Wang, C., Berda, E.B., (2013) Chem. Commun., 49, pp. 4178-4180; Wen, J., Yuan, L., Yang, Y., Liu, L., Zhao, H., (2013) ACS Macro Lett., 2, pp. 100-106; Dobish, J.N., Hamilton, S.K., Harth, E., (2012) Polym. Chem., 3, pp. 857-860; Ormategui, N., Garcia, I., Padro, D., Cabanero, G., Grande, H.J., Loinaz, I., (2012) Soft Matter, 8, pp. 734-740; Schmidt, B.V.K.J., Fechler, N., Falkenhagen, J., Lutz, J.-F., (2011) Nat. Chem., 3, pp. 234-238; Wang, P., Pu, H., Jin, M., (2011) J. Polym. Sci., Part A: Polym. Chem., 49, pp. 5133-5141; Zhu, B., Qian, G., Xiao, Y., Deng, S., Wang, M., Hu, A., (2011) J. Polym. Sci., Part A: Polym. Chem., 49, pp. 5330-5338; Perez-Baena, I., Loinaz, I., Padro, D., García, I., Grande, H.J., Odriozola, I., (2010) J. Mater. Chem., 20, pp. 6916-6916; Beck, J.B., Killops, K.L., Kang, T., Sivanandan, K., Bayles, A., MacKay, M.E., Wooley, K.L., Hawker, C.J., (2009) Macromolecules, 42, pp. 5629-5635; De Luzuriaga, A.R., Ormategui, N., Grande, H.J., Odriozola, I., Pomposo, J.A., Loinaz, I., (2008) Macromol. Rapid Commun., 29, pp. 1156-1160; He, J., Tremblay, L., Lacelle, S., Zhao, Y., (2011) Soft Matter, 7, pp. 2380-2386; Murray, B.S., Fulton, D.A., (2011) Macromolecules, 44, pp. 7242-7252; Tuten, B.T., Chao, D., Lyon, C.K., Berda, E.B., (2012) Polym. Chem., 3, pp. 3068-3071; Gillissen, M.A.J., Terashima, T., Meijer, E.W., Palmans, A.R.A., Voets, I.K., (2013) Macromolecules, , 10.1021/ma4006846; Stals, P.J.M., Gillissen, M.A.J., Nicolay, R., Palmans, A.R.A., Meijer, E.W., (2013) Polym. Chem., 4, pp. 2584-2597; Hosono, N., Gillissen, M.A.J., Li, Y., Sheiko, S.S., Palmans, A.R.A., Meijer, E.W., (2013) J. Am. Chem. Soc., 135, pp. 501-510; Altintas, O., Lejeune, E., Gerstel, P., Barner-Kowollik, C., (2012) Polym. Chem., 3, pp. 640-651; Appel, E.A., Dyson, J., Del Barrio, J., Walsh, Z., Scherman, O.A., (2012) Angew. Chem., Int. Ed., 51, pp. 4185-4189; Gillissen, M.A.J., Voets, I.K., Meijer, E.W., Palmans, A.R.A., (2012) Polym. Chem., 3, pp. 3166-3174; Mes, T., Van Der Weegen, R., Palmans, A.R.A., Meijer, E.W., (2011) Angew. Chem., Int. Ed., 50, pp. 5085-5089; Altintas, O., Rudolph, T., Barner-Kowollik, C., (2011) J. Polym. Sci., Part A: Polym. Chem., 49, pp. 2566-2576; Terashima, T., Mes, T., De Greef, T.F.A., Gillissen, M.A.J., Besenius, P., Palmans, A.R.A., Meijer, E.W., (2011) J. Am. Chem. Soc., 133, pp. 4742-4745; Altintas, O., Gerstel, P., Dingenouts, N., Barner-Kowollik, C., (2010) Chem. Commun., 46, pp. 6291-6293; Foster, E.J., Berda, E.B., Meijer, E.W., (2009) J. Am. Chem. Soc., 131, pp. 6964-6966; Seo, M., Beck, B.J., Paulusse, J.M.J., Hawker, C.J., Kim, S.Y., (2008) Macromolecules, 41, pp. 6413-6418; Sanchez-Sanchez, A., Akbari, S., Etxeberria, A., Arbe, A., Gasser, U., Moreno, A.J., Colmenero, J., Pomposo, J.A., (2013) ACS Macro Lett., 2, pp. 491-495; Bertin, P.A., Gibbs, J.M., Shen, C.K.F., Thaxton, C.S., Russin, W.A., Mirkin, C.A., Nguyen, S.T., (2006) J. Am. Chem. Soc., 128, pp. 4168-4169; Xu, F.J., Yang, W.T., (2011) Prog. Polym. Sci., 36, pp. 1099-1131; Matyjaszewski, K., (2012) Macromolecules, 45, pp. 4015-4039; Shipp, D.A., (2011) Polym. Rev., 51, pp. 99-103; Rosen, B.M., Percec, V., (2009) Chem. Rev., 109, pp. 5069-5119; Braunecker, W.A., Matyjaszewski, K., (2007) Prog. Polym. Sci., 32, pp. 93-146; Moad, G., Rizzardo, E., Thang, S.H., (2008) Acc. Chem. Res., 41, pp. 1133-1142; Goldmann, A.S., Glassner, M., Inglis, A.J., Barner-Kowollik, C., (2013) Macromol. Rapid Commun., 34, pp. 810-849; Yang, D., Feng, C., Hu, J., (2013) Polym. Chem., 4, pp. 2384-2394; Tunca, U., (2013) Macromol. Rapid Commun., 34, pp. 38-46; Altintas, O., Vogt, A.P., Barner-Kowollik, C., Tunca, U., (2012) Polym. Chem., 3, pp. 34-45; Kempe, K., Krieg, A., Becer, C.R., Schubert, U.S., (2012) Chem. Soc. Rev., 41, pp. 176-191; Golas, P.L., Matyjaszewski, K., (2010) Chem. Soc. Rev., 39, pp. 1338-1354; Sumerlin, B.S., Vogt, A.P., (2010) Macromolecules, 43, pp. 1-13; Becer, C.R., Hoogenboom, R., Schubert, U.S., (2009) Angew. Chem., Int. Ed., 48, pp. 4900-4908; Iha, R.K., Wooley, K.L., Nystrom, A.M., Burke, D.J., Kade, M.J., Hawker, C.J., (2009) Chem. Rev., 109, pp. 5620-5686; Nicolas, J., Guillaneuf, F., Lefay, C., Bertin, D., Gigmes, D., Charleux, B., (2013) Prog. Polym. Sci., 38, pp. 63-235; Grubbs, R.B., (2011) Polym. Rev., 51, pp. 104-137; Barner-Kowollik, C., Du Prez, F.E., Espeel, P., Hawker, C.J., Junkers, T., Schlaad, H., Van Camp, W., (2011) Angew. Chem., Int. Ed., 50, pp. 60-62; 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, pp. 762-766; Glassner, M., Oehlenschlaeger, K.K., Gruendling, T., Barner-Kowollik, C., (2011) Macromolecules, 44, pp. 4681-4689; Winkler, M., Müller, J.O., Oehlenschlaeger, K.K., Montero De Espinosa, L., Meier, M.A.R., Barner-Kowollik, C., (2012) Macromolecules, 45, pp. 5012-5019; Altintas, O., Hizal, G., Tunca, U., (2009) Des. Monomers Polym., 12, pp. 83-98; Gacal, B., Durmaz, H., Tasdelen, M.A., Hizal, G., Tunca, U., Yagci, Y., Demirel, A.L., (2006) Macromolecules, 39, pp. 5330-5336; Altintas, O., Yankul, B., Hizal, G., Tunca, U., (2006) J. Polym. Sci., Polym. Chem., 44, pp. 6458-6465; Altintas, O., Muller, T., Lejeune, E., Plietzsch, O., Bräse, S., Barner-Kowollik, C., (2012) Macromol. Rapid Commun., 33, pp. 977-983; Rabani, E., Reichman, D.R., Geissler, P.L., Brus, L.E., (2003) Nature, 426, pp. 271-274; Cherian, E.A., Sun, F.C., Sheiko, S.S., Coates, G.W., (2007) J. Am. Chem. Soc., 129, pp. 11350-11351; Berda, E.B., Foster, E.J., Meijer, E.W., (2010) Macromolecules, 43, pp. 1430-1437; Van Roekel, H.W.H., Stals, P.J.M., Gillissen, M.A.J., Hilbers, P.A.J., Markvoort, A.J., De Greef, T.F.A., (2013) Chem. Commun., 49, pp. 3122-3124
Keywords: 4-chloromethylstyrene, Azide-alkyne cycloaddition, Intra-molecular cross-linking, Nitroxide mediated radical polymerization, Nuclear magnetic resonance(NMR), Polymeric nanoparticles, Postpolymerization modifications, Single polymer chains, Atomic force microscopy, Chains, Copolymers, Crosslinking, Cycloaddition, Dynamic light scattering, Functional groups, Hydrocarbons, Nanoparticles, Nuclear magnetic resonance spectroscopy, Polyethylene glycols, Polyethylene oxides, Styrene, Polymers
DOI: 10.1021/ma4015033
ISSN: 00249297
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 04:21

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