Photo- and Metallo-responsive N-Alkyl α-Bisimines as Orthogonally Addressable Main-Chain Functional Groups in Metathesis Polymers

Greb, L., Mutlu, H., Barner-Kowollik, C., & Lehn, J. M. (2016) Photo- and Metallo-responsive N-Alkyl α-Bisimines as Orthogonally Addressable Main-Chain Functional Groups in Metathesis Polymers. Journal of the American Chemical Society, 138(4).

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Abstract

N-alkyl α-bisimines were employed as main-chain functional groups in acyclic diene metathesis (ADMET)-polymers, conferring dual responsiveness for the controlled switching of the polymeric particle shape with light and metal ions. Photochemical Z/E-isomerization leads to a significant and reversible change in hydrodynamic volume, thus introducing simple imines as novel photoswitches for light-responsive materials. Mild imine-directed CH activation by Pd(OAc)2 is demonstrated as a new single-chain nanoparticle (SCNP) folding process, enabling a controlled atom- and step-economic SCNP synthesis. The combination of light- and metallo-responsiveness in the same polymer provides the ability for orthogonal switching, a valuable tool for advanced functional material design. © 2015 American Chemical Society.

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ID Code: 99463
Item Type: Journal Article
Refereed: Yes
Additional Information: Cited By :1
Export Date: 5 September 2016
CODEN: JACSA
Correspondence Address: Barner-Kowollik, C.; Soft Matter Synthesis Laboratory, Institut für Biologische Grenzflächen, Karlsruhe Institute of Technology (KIT), Hermann-von-Helmholtz-Platz 1, Germany; email: christopher.barner-kowollik@kit.edu
Chemicals/CAS: imine, 13774-92-0
Funding Details: ERC, European Research Council
References: Liu, F., Urban, M.W., (2010) Prog. Polym. Sci., 35, p. 3; Roy, D., Cambre, J.N., Sumerlin, B.S., (2010) Prog. Polym. Sci., 35, p. 278; Stuart, M.A.C., Huck, W.T.S., Genzer, J., Muller, M., Ober, C., Stamm, M., Sukhorukov, G.B., Minko, S., (2010) Nat. Mater., 9, p. 101; Theato, P., Sumerlin, B.S., O'Reilly, R.K., Epps, T.H., III, (2013) Chem. Soc. Rev., 42, p. 7055; Abendroth, J.M., Bushuyev, O.S., Weiss, P.S., Barrett, C.J., (2015) ACS Nano, 9, p. 7746; Kikuchi, A., Okano, T., (2002) Adv. Drug Delivery Rev., 54, p. 53; Baughman, R.H., (2005) Science, 308, p. 63; Madden, J.D., (2007) Science, 318, p. 1094; Burnworth, M., Tang, L., Kumpfer, J.R., Duncan, A.J., Beyer, F.L., Fiore, G.L., Rowan, S.J., Weder, C., (2011) Nature, 472, p. 334; Irie, M., (1990) Pure Appl. Chem., 62, p. 1495; Dai, S., Ravi, P., Tam, K.C., (2009) Soft Matter, 5, p. 2513; Lehn, J.-M., (2005) Prog. Polym. Sci., 30, p. 814; Roy, N., Bruchmann, B., Lehn, J.-M., (2015) Chem. Soc. Rev., 44, p. 3786; Feringa, B.L., (2011) Molecular Switches, , Wiley-VCH: Weinheim; Kumar, G.S., Neckers, D.C., (1989) Chem. Rev., 89, p. 1915; Natansohn, A., Rochon, P., (2002) Chem. Rev., 102, p. 4139; Zhao, Y., Ikeda, T., (2009) Smart Light-responsive Materials Azobenzene-containing Polymers and Liquid Crystals, , J. Wiley & Sons: Hoboken, NJ; Hugel, T., Holland, N.B., Cattani, A., Moroder, L., Seitz, M., Gaub, H.E., (2002) Science, 296, p. 1103; Bléger, D., Liebig, T., Thiermann, R., Maskos, M., Rabe, J.P., Hecht, S., (2011) Angew. Chem., Int. Ed., 50, p. 12559; Lee, C.-L., Liebig, T., Hecht, S., Bléger, D., Rabe, J.P., (2014) ACS Nano, 8, p. 11987; Maayan, G.G., Albrecht, M., (2013) Metallofoldamers: Supramolecular Architectures from Helicates to Biomimetics, , Wiley, Chichester, UK; Lehn, J.-M., (2015) Angew. Chem., Int. Ed., 54, p. 3276; Lehn, J.M., Barboiu, M., Stadler, A.-M., (2015) Angew. Chem., Int. Ed., 54, p. 3276; Altintas, O., Barner-Kowollik, C., (2012) Macromol. Rapid Commun., 33, p. 958; Altintas, O., Barner-Kowollik, C., (2016) Macromol. Rapid Commun.; Huo, M., Wang, N., Fang, T., Sun, M., Wei, Y., Yuan, J., (2015) Polymer, 66, p. A11; 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; Mavila, S., Eivgi, O., Berkovich, I., Lemcoff, N.G., (2015) Chem. Rev.; 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, p. 4168; Perez-Baena, I., Loinaz, I., Padro, D., Garcia, I., Grande, H.J., Odriozola, I., (2010) J. Mater. Chem., 20, p. 6916; Pomposo, J.A., (2014) Polym. Int., 63, p. 589; 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; Huerta, E., Stals, P.J.M., Meijer, E.W., Palmans, A.R.A., (2013) Angew. Chem., Int. Ed., 52, p. 2906; Willenbacher, J., Altintas, O., Trouillet, V., Knöfel, N., Monteiro, M.J., Roesky, P.W., Barner-Kowollik, C., (2015) Polym. Chem., 6, p. 4358; Willenbacher, J., Altintas, O., Roesky, P.W., Barner-Kowollik, C., (2014) Macromol. Rapid Commun., 35, p. 45; Sanchez-Sanchez, A., Arbe, A., Colmenero, J., Pomposo, J.A., (2014) ACS Macro Lett., 3, p. 439; Sanchez-Sanchez, A., Arbe, A., Kohlbrecher, J., Colmenero, J., Pomposo, J.A., (2015) Macromol. Rapid Commun., 36, p. 1592; Jeong, J., Lee, Y.-J., Kim, B., Kim, B., Jung, K.-S., Paik H.-j., (2015) Polym. Chem., 6, p. 3392; Mavila, S., Diesendruck, C.E., Linde, S., Amir, L., Shikler, R., Lemcoff, N.G., (2013) Angew. Chem., Int. Ed., 52, p. 5767; Mavila, S., Rozenberg, I., Lemcoff, N.G., (2014) Chem. Sci., 5, p. 4196; Guragain, S., Bastakoti, B.P., Malgras, V., Nakashima, K., Yamauchi, Y., (2015) Chem. - Eur. J., 21, p. 13164; McCarty, C.G., (2010) Carbon-Nitrogen Double Bonds (1970), p. 363. , John Wiley & Sons, Ltd. Chichester, UK; Koten, G.V., Vrieze, K., (1982) Advances in Organometallic Chemistry, 21, p. 151. , Stone, F. G. A. Robert, W. Academic Press: New York, Vol; Greb, L., Lehn, J.-M., (2014) J. Am. Chem. Soc., 136, p. 13114; Greb, L., Eichhöfer, A., Lehn, J.-M., (2015) Angew. Chem., 127, p. 14553; Greb, L.; Eichhöfer, A.; Lehn, J. M. Submitted, 2015Caram, J.A., Piro, O.E., Castellano, E.E., Mirífico, M.V., Vasini, E.J., (2006) J. Phys. Org. Chem., 19, p. 229; Kubota, M., Covarrubias, D., Pye, C., Fronczek, F.R., Isovitsch, R., (2013) J. Coord. Chem., 66, p. 1350; Mutlu, H., De Espinosa, L.M., Meier, M.A.R., (2011) Chem. Soc. Rev., 40, p. 1404; Atallah, P., Wagener, K.B., Schulz, M.D., (2013) Macromolecules, 46, p. 4735; Wagner, H.L., (1985) J. Phys. Chem. Ref. Data, 14, pp. 1101-1106. , The relation V = 0.4KMn(a+1), where K = 0.01363 and a = 0.7 are the Mark-Houwink parameters for PS in THF, is used; see; Pickett, S.D., Sternberg, M.J.E.J., (1993) J. Mol. Biol., 231, p. 825; Kawakatsu, T., (2004) Statistical Physics of Polymers: An Introduction, , Springer: Berlin/New York; Baldwin, R.L.J., (2007) J. Mol. Biol., 371, p. 283; Cope, A.C., Siekman, R.W.J., (1965) J. Am. Chem. Soc., 87, p. 3272; Powers, D.C., Geibel, M.A.L., Klein, J.E.M.N., Ritter, T.J., (2009) J. Am. Chem. Soc., 131, p. 17050; Lyons, T.W., Sanford, M.S., (2010) Chem. Rev., 110, p. 1147; Jin, Y., Wang, Q., Taynton, P., Zhang, W., (2014) Acc. Chem. Res., 47, p. 1575; Lehn, J.-M., (2013) Hierarchical Macromolecular Structures: 60 Years after the Staudinger Nobel Prize I, 261, p. 155. , Percec, V. Springer International Publishing: Berlin/Heidelberg, Vol
Keywords: Chains, Chemical activation, Design, Functional materials, Metal ions, Metals, Nitrogen compounds, Palladium, Synthesis (chemical), Acyclic diene metathesis, C-h activation, Controlled switching, Folding process, Hydrodynamic volumes, Light-responsive materials, Polymeric particles, Reversible change, Polymers, alkadiene, alkyl group, functional group, imine, nanoparticle, transition element, Article, atom, chemical reaction, complex formation, hydrodynamics, isomerization, molecular weight, nuclear magnetic resonance spectroscopy, particle size, photochemistry, photon correlation spectroscopy, polymerization, process design, size exclusion chromatography
DOI: 10.1021/jacs.5b12198
ISSN: 00027863
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: 23 Sep 2016 03:12

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