Photo-induced sequence defined macromolecules via hetero bifunctional synthons

Zydziak, N., Feist, F., Huber, B., Mueller, J. O., & Barner-Kowollik, C. (2015) Photo-induced sequence defined macromolecules via hetero bifunctional synthons. Chemical Communications, 51(10).

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We report the first photochemical protocol for the generation of sequence defined macromolecules employing two hetero bifunctional photoreactive synthons, exploiting the orthogonal nature of photochemical - via the use of caged dienes - and thermally driven ligation protocols. We demonstrate that the iterative alternating synthon addition to an initial bifunctional core under irradiation at ambient temperature enables the generation of a macromolecule with up to 10 units (M = 3231.58 g mol-1, Crossed D sign = 1.00). The resulting macromolecules are monodisperse and feature absolute chain end fidelity. The unit-by-unit construction of the macromolecule is evidenced by Nuclear Magnetic Resonance Spectroscopy, Electrospray Ionization Mass Spectrometry and Size Exclusion Chromatography. The fundamental principle demonstrated herein paves the way for employing photochemical strategies for the design of sequence defined polymers. © The Royal Society of Chemistry 2015.

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ID Code: 99452
Item Type: Journal Article
Refereed: Yes
Additional Information: Cited By :14
Export Date: 5 September 2016
Correspondence Address: Barner-Kowollik, C.; Soft Matter Synthesis Laboratory, Institut für Biologische Grenzflächen, Karlsruhe Institute of Technology (KIT), Hermann-von-Helmholtz-Platz 1, Germany
References: Lutz, J.-F., Ouchi, M., Liu, D.R., Sawamoto, M., (2013) Science, 341, p. 1238149; Badi, N., Lutz, J.-F., (2009) Chem. Soc. Rev., 38, pp. 3383-3390; Vandenbergh, J., Reekmans, G., Adriaensens, P., Junkers, T., (2013) Chem. Commun., 49, pp. 10358-10360; Gody, G., Maschmeyer, T., Zetterlund, P.B., Perrier, S., (2014) Macromolecules, 47, pp. 639-649; Gody, G., Maschmeyer, T., Zetterlund, P., Perrier, S., (2013) Nat. Commun., 4, p. 2505; Zhang, Q., Anastasaki, A., Li, G.-Z., Haddleton, A.J., Wilson, P., Haddleton, D.M., (2014) Polym. Chem., 5, pp. 3876-3883; Boyer, C., Zetterlund, P.B., Whittaker, M.R.J., (2014) J. Polym. Sci., Part A: Polym. Chem., 52, pp. 2083-2098; Anastasaki, A., Nikolaou, V., Pappas, G.S., Zhang, Q., Wan, C., Wilson, P., Davis, T.P., Haddleton, D.M., (2014) Chem. Sci., 5, pp. 3536-3542; Srichan, S., Kayunkid, N., Oswald, L., Lotz, B., Lutz, J.-F., (2014) Macromolecules, 47, pp. 1570-1577; Zamfir, M., Lutz, J.-F., (2012) Nat. Commun., 3, p. 1138; Srichan, S., Mutlu, H., Badi, N., Lutz, J.-F., (2014) Angew. Chem., Int. Ed., 53, pp. 9231-9235; Roy, R.K., Lutz, J.-F., (2014) J. Am. Chem. Soc., 136, pp. 12888-12891; Schmidt, B.V.K.J., Barner-Kowollik, C., (2013) Nat. Chem., 5, pp. 990-992; Ida, S., Ouchi, M., Sawamoto, M., (2010) J. Am. Chem. Soc., 132, pp. 14748-14750; Edwardson, T.G.W., Carneiro, K.M.M., Serpell, C.J., Sleiman, H.F., (2014) Angew. Chem., Int. Ed., 53, pp. 4567-4571; Rosenbaum, D.M., Liu, D.R., (2003) J. Am. Chem. Soc., 125, pp. 13924-13925; Niu, J., Hili, R., Liu, D.R., (2013) Nat. Chem., 5, pp. 282-292; Espeel, P., Carrette, L.L.G., Bury, K., Capenberghs, S., Martins, J.C., Du Prez, F.E., Madder, A., (2013) Angew. Chem., Int. Ed., 52, pp. 13261-13264; Lewandowski, B., De Bo, G., Ward, J.W., Papmeyer, M., Kuschel, S., Aldegunde, M.J., Gramlich, P.M.E., Leigh, D.A., (2013) Science, 339, pp. 189-193; Trinh, T.T., Oswald, L., Chan-Seng, D., Lutz, J.-F., (2014) Macromol. Rapid Commun., 35, pp. 141-145; Solleder, S.C., Meier, M.A.R., (2014) Angew. Chem., Int. Ed., 53, pp. 711-713; Kolb, H.C., Finn, M.G., Sharpless, K.B., (2001) Angew. Chem., Int. Ed., 40, pp. 2004-2021; Barner-Kowollik, C., Du Prez, F.E., Espeel, P., Hawker, C.J., (2001) Angew. Chem., Int. Ed., 50, pp. 60-62; Göstl, R., Hecht, S., (2014) Angew. Chem., Int. Ed., 53, pp. 8784-8787; Gruendling, T., Oehlenschlaeger, K.K., Frick, E., Glassner, M., Schmid, C., Barner-Kowollik, C., (2011) Macromol. Rapid Commun., 32, pp. 807-812; 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; Winkler, M., Müller, J.O., Oehlenschläger, K.K., Montero De Espinosa, L., Meier, M.A.R., Barner-Kowollik, C., (2012) Macromolecules, 45, pp. 5012-5019; Glassner, M., Oehlenschlaeger, K.K., Welle, A., Bruns, M., Barner-Kowollik, C., (2013) Chem. Commun., 49, pp. 633-635; Pauloehrl, T., Delaittre, G., Winkler, V., Welle, A., Bruns, M., Börner, H.G., Greiner, A.M., Barner-Kowollik, C., (2012) Angew. Chem., Int. Ed., 51, pp. 1071-1074
Keywords: alkadiene, hetero bifunctional synthon, polymer, unclassified drug, Article, chemical composition, chemical structure, covalent bond, electrospray mass spectrometry, environmental temperature, gel permeation chromatography, irradiation, macromolecule, molecular weight, photoreactivity, proton nuclear magnetic resonance
DOI: 10.1039/c4cc08756a
ISSN: 13597345
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 02:57

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