Design and Synthesis of Triblock Copolymers for Creating Complex Secondary Structures by Orthogonal Self-Assembly

Altintas, O., Artar, M., Ter Huurne, G., Voets, I. K., Palmans, A. R. A., Barner-Kowollik, C., & Meijer, E. W. (2015) Design and Synthesis of Triblock Copolymers for Creating Complex Secondary Structures by Orthogonal Self-Assembly. Macromolecules, 48(24).

View at publisher

Abstract

We herein report the synthesis and characterization of ABC-type triblock copolymers containing two complementary association motifs and investigate their folding into well-defined polymeric nanoparticles under diluted conditions via intramolecular orthogonal hydrogen bonding. The precursor ABC-type triblock copolymers are prepared via reversible addition-fragmentation chain transfer (RAFT) polymerization bearing primary alkyl bromide on A, protected alkyne on B, and protected hydroxyl pendant groups on the C units. The dithioester groups of the RAFT polymers are quantitatively removed by radical-induced reduction before the side-chain functionalization. The complementary motifs, i.e., Hamilton wedge (HW, A block), benzene-1,3,5-tricarboxamide (BTA, B block), and cyanuric acid (CA, C block), are incorporated into the linear triblock copolymers side chains via postfunctionalization. The self-assembly processes of the HW and CA supramolecular motifs are followed by nuclear magnetic resonance (1H NMR) spectroscopy at ambient and elevated temperature in various solvents. The helical BTA stack formation is monitored by circular dichroism (CD) spectroscopy. In addition, the final aggregates formed by these two orthogonal forces, namely HW-CA pseudo-cross-linking and BTA stacking, are characterized by static and dynamic light scattering (SLS and DLS) as well as atomic force microscopy (AFM). © 2015 American Chemical Society.

Impact and interest:

3 citations in Scopus
Search Google Scholar™
3 citations in Web of Science®

Citation counts are sourced monthly from Scopus and Web of Science® citation databases.

These databases contain citations from different subsets of available publications and different time periods and thus the citation count from each is usually different. Some works are not in either database and no count is displayed. Scopus includes citations from articles published in 1996 onwards, and Web of Science® generally from 1980 onwards.

Citations counts from the Google Scholar™ indexing service can be viewed at the linked Google Scholar™ search.

ID Code: 99419
Item Type: Journal Article
Refereed: Yes
Additional Information: Cited By :1
Export Date: 5 September 2016
CODEN: MAMOB
Correspondence Address: Palmans, A.R.A.; Laboratory of Macromolecular and Organic ChemistryNetherlands; email: a.palmans@tue.nl
Funding Details: 246829, ERC, European Research Council
Funding Details: FP7/2007?2013, ERC, European Research Council
References: Anfinsen, C.B., (1973) Science, 181, p. 223; Dobson, C.M., (2003) Nature, 426, p. 884; Branden, C.T.J., (1998) Introduction to Protein Structure, , Garland Publishing: New York; Altintas, O., Barner-Kowollik, C., (2012) Macromol. Rapid Commun., 33, p. 958; Ouchi, M., Badi, N., Lutz, J.-F., Sawamoto, M., (2011) Nat. Chem., 3, p. 917; Lutz, J.-F., Ouchi, M., Liu, D.R., Sawamoto, M., (2013) Science, 341, p. 1238149; Lyon, C.K., Prasher, A., Hanlon, A.M., Tuten, B.T., Tooley, C.A., Frank, P.G., Berda, E.B., (2015) Polym. Chem., 6, p. 181; Gonzalez-Burgos, M., Latorre-Sanchez, A., Pomposo, J.A., (2015) Chem. Soc. Rev., 44, pp. 6122-6142; Altintas, O., Barner-Kowollik, C., (2016) Macromol. Rapid Commun.; Elsabahy, M., Wooley, K.L., (2012) Chem. Soc. Rev., 41, p. 2545; Artar, M., Huerta, E., Meijer, E.W., Palmans, A.R.A., (2014) Sequence-Controlled Polymers: Synthesis, Self-Assembly, and Properties, 1170, p. 313. , In; American Chemical Society: Washington, DC, Vol; Rao, J.P., Geckeler, K.E., (2011) Prog. Polym. Sci., 36, p. 887; Sanchez-Sanchez, A., Pérez-Baena, I., Pomposo, J., (2013) Molecules, 18, p. 3339; Perez-Baena, I., Asenjo-Sanz, I., Arbe, A., Moreno, A.J., Lo Verso, F., Colmenero, J., Pomposo, J.A., (2014) Macromolecules, 47, p. 8270; Hansell, C.F., Lu, A., Patterson, J.P., O'Reilly, R.K., (2014) Nanoscale, 6, p. 4102; Willenbacher, J., Wuest, K.N.R., Mueller, J.O., Kaupp, M., Wagenknecht, H.-A., Barner-Kowollik, C., (2014) ACS Macro Lett., 3, p. 574; Willenbacher, J., Altintas, O., Roesky, P.W., Barner-Kowollik, C., (2014) Macromol. Rapid Commun., 35, p. 45; Shishkan, O., Zamfir, M., Gauthier, M.A., Borner, H.G., Lutz, J.-F., (2014) Chem. Commun., 50, p. 1570; Sanchez-Sanchez, A., Arbe, A., Colmenero, J., Pomposo, J.A., (2014) ACS Macro Lett., 3, p. 439; Frank, P.G., Tuten, B.T., Prasher, A., Chao, D., Berda, E.B., (2014) Macromol. Rapid Commun., 35, p. 249; Sanchez-Sanchez, A., Fulton, D.A., Pomposo, J.A., (2014) Chem. Commun., 50, p. 1871; Whitaker, D.E., Mahon, C.S., Fulton, D.A., (2013) Angew. Chem., Int. Ed., 52, p. 956; Tuten, B.T., Chao, D., Lyon, C.K., Berda, E.B., (2012) Polym. Chem., 3, p. 3068; Murray, B.S., Fulton, D.A., (2011) Macromolecules, 44, p. 7242; Lu, J., Ten Brummelhuis, N., Weck, M., (2014) Chem. Commun., 50, p. 6225; Willenbacher, J., Schmidt, B.V.K.J., Schulze-Suenninghausen, D., Altintas, O., Luy, B., Delaittre, G., Barner-Kowollik, C., (2014) Chem. Commun., 50, p. 7056; Stals, P.J.M., Gillissen, M.A.J., Nicolay, R., Palmans, A.R.A., Meijer, E.W., (2013) Polym. Chem., 4, p. 2584; Artar, M., Terashima, T., Sawamoto, M., Meijer, E.W., Palmans, A.R.A., (2014) J. Polym. Sci., Part A: Polym. Chem., 52, p. 12; Artar, M., Souren, E.R.J., Terashima, T., Meijer, E.W., Palmans, A.R.A., (2015) ACS Macro Lett., 4, p. 1099; Liu, Y., Pauloehrl, T., Presolski, S.I., Albertazzi, L., Palmans, A.R.A., Meijer, E.W., (2015) J. Am. Chem. Soc., 137, p. 13096; Ter Huurne, G.M., Gillissen, M.A.J., Palmans, A.R.A., Voets, I.K., Meijer, E.W., (2015) Macromolecules, 48, p. 3949; Lo Verso, F., Pomposo, J.A., Colmenero, J., Moreno, A.J., (2014) Soft Matter, 10, p. 4813; Moreno, A.J., Lo Verso, F., Sanchez-Sanchez, A., Arbe, A., Colmenero, J., Pomposo, J.A., (2013) Macromolecules, 46, p. 9748; Hosono, N., Gillissen, M.A.J., Li, Y., Sheiko, S.S., Palmans, A.R.A., Meijer, E.W., (2013) J. Am. Chem. Soc., 135, p. 501; Hosono, N., Palmans, A.R.A., Meijer, E.W., (2014) Chem. Commun., 50, p. 7990; Hosono, N., Stals, P.J.M., Palmans, A.R.A., Meijer, E.W., (2014) Chem. - Asian J., 9, p. 1099; Berda, E.B., Foster, E.J., Meijer, E.W., (2010) Macromolecules, 43, p. 1430; Foster, E.J., Berda, E.B., Meijer, E.W., (2009) J. Am. Chem. Soc., 131, p. 6964; Mes, T., Van Der Weegen, R., Palmans, A.R.A., Meijer, E.W., (2011) Angew. Chem., Int. Ed., 50, p. 5085; 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, p. 4742; Altintas, O., Gerstel, P., Dingenouts, N., Barner-Kowollik, C., (2010) Chem. Commun., 46, p. 6291; Altintas, O., Lejeune, E., Gerstel, P., Barner-Kowollik, C., (2012) Polym. Chem., 3, p. 640; Altintas, O., Krolla-Sidenstein, P., Gliemann, H., Barner-Kowollik, C., (2014) Macromolecules, 47, p. 5877; Romulus, J., Weck, M., (2013) Macromol. Rapid Commun., 34, p. 1518; Pomposo, J.A., Perez-Baena, I., Lo Verso, F., Moreno, A.J., Arbe, A., Colmenero, J., (2014) ACS Macro Lett., 3, p. 767; Ladmiral, V., Mantovani, G., Clarkson, G.J., Cauet, S., Irwin, J.L., Haddleton, D.M., (2006) J. Am. Chem. Soc., 128, p. 4823; Altintas, O., Muller, T., Lejeune, E., Plietzsch, O., Bräse, S., Barner-Kowollik, C., (2012) Macromol. Rapid Commun., 33, p. 977; Börner, H.G., Duran, D., Matyjaszewski, K., Da Silva, M., Sheiko, S.S., (2002) Macromolecules, 35, p. 3387; Lee, H.-I., Matyjaszewski, K., Yu, S., Sheiko, S.S., (2005) Macromolecules, 38, p. 8264; Chen, M., Moad, G., Rizzardo, E., (2009) J. Polym. Sci., Part A: Polym. Chem., 47, p. 6704; Khanna, K., Varshney, S., Kakkar, A., (2010) Macromolecules, 43, p. 5688; Stals, P.J.M., Cheng, C.-Y., Van Beek, L., Wauters, A.C., Palmans, A.R.A., Han, S., Meijer, E.W., (2015) Chem. Sci., , submitted; Ito, H., Arimoto, K., Sensul, H.-O., Hosomi, A., (1997) Tetrahedron Lett., 38, p. 3977; Altintas, O., Rudolph, T., Barner-Kowollik, C., (2011) J. Polym. Sci., Part A: Polym. Chem., 49, p. 2566; Altintas, O., Schulze-Suenninghausen, D., Luy, B., Barner-Kowollik, C., (2013) ACS Macro Lett., 2, p. 211; Altintas, O., Schulze-Suenninghausen, D., Luy, B., Barner-Kowollik, C., (2015) Eur. Polym. J., 62, p. 409; Altintas, O., Tunca, U., Barner-Kowollik, C., (2011) Polym. Chem., 2, p. 1146; Gillissen, M.A.J., Terashima, T., Meijer, E.W., Palmans, A.R.A., Voets, I.K., (2013) Macromolecules, 46, p. 4120; Stals, P.J.M., Gillissen, M.A.J., Paffen, T.F.E., De Greef, T.F.A., Lindner, P., Meijer, E.W., Palmans, A.R.A., Voets, I.K., (2014) Macromolecules, 47, p. 2947
Keywords: Atomic force microscopy, Block copolymers, Chains, Circular dichroism spectroscopy, Dichroism, Dynamic light scattering, Free radical polymerization, Hydrogen bonds, Ionic liquids, Light scattering, Nuclear magnetic resonance, Nuclear magnetic resonance spectroscopy, Self assembly, Linear triblock copolymers, Polymeric nanoparticles, Post-functionalization, Reversible addition-fragmentation chain transfer polymerization, Self assembly process, Side-chain functionalization, Static and dynamic light scattering, Synthesis and characterizations, Synthesis (chemical)
DOI: 10.1021/acs.macromol.5b01990
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: 26 Sep 2016 00:35

Export: EndNote | Dublin Core | BibTeX

Repository Staff Only: item control page