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Photo-Reversibility of Cinnamylidene Acetic Acid Derived Crosslinks in Poly(ε-caprolactone) Networks

Published online by Cambridge University Press:  18 May 2015

Florian Störmann ,
Christian Wischke  and
Andreas Lendlein
Florian Störmann
Affiliation:
Helmholtz-Zentrum Geesthacht, Institute of Biomaterial Science and Berlin-Brandenburg Center for Regenerative Therapies, Kantstraße 55, 14513 Teltow, Germany. University of Potsdam, Institute of Chemistry, 14469 Potsdam, Germany.
Christian Wischke
Affiliation:
Helmholtz-Zentrum Geesthacht, Institute of Biomaterial Science and Berlin-Brandenburg Center for Regenerative Therapies, Kantstraße 55, 14513 Teltow, Germany.
Andreas Lendlein
Affiliation:
Helmholtz-Zentrum Geesthacht, Institute of Biomaterial Science and Berlin-Brandenburg Center for Regenerative Therapies, Kantstraße 55, 14513 Teltow, Germany. University of Potsdam, Institute of Chemistry, 14469 Potsdam, Germany.
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Abstract

Photoswitchable polymeric materials comprise moieties that undergo light-induced chemical reactions or conformational alteration. The reversibility of photo-responsive molecular switches has an influence on material functions observed on the macroscopic level such as reversibility of shape switching, especially with regard to the number of cycles. Cinnamylidene acetic acid (CAA) has received attention due to its reversible dimerization by [2+2] cycloaddition reactions. In the present study, possible side-reactions during photo-scission of the CAA dimers as netpoints in poly(ε-caprolactone) based materials were studied by fluorescence spectroscopy, HPLC and 1H,1H-COSY. Liberation of fluorescent fragments, which have their origin in the various dimer structures, could only be found in small amounts, while a non-identified species seems to be generated during dimerization and photo-scission. The results furthermore suggest that CAA-based switches in PCL-networks do not provide full reversibility of netpoint formation under the examined conditions, due to non-selective side-reactions, which could lead to an attenuation of the macroscopic effect in multiple photo-cycles. In perspective, the design of CAA derivatives with enhanced photo-reversibility should be targeted.

Keywords

polymerphotochemicalstructural
Type
Articles
Information
MRS Online Proceedings Library (OPL) , Volume 1718: Symposium B – Multifunctional Polymeric and Hybrid Materials , 2015 , pp. 49 - 54
Copyright
Copyright © Materials Research Society 2015 

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References

REFERENCES

Hoogen, N. and Nuyken, O., J. Polym. Sci. Part A: Polym Chem. 38, 1903 (2000).3.0.CO;2-Q>CrossRefGoogle Scholar
Jin, Q., Liu, G., Ji, J., Eur, Polym. J. 46, 2120 (2010).CrossRefGoogle Scholar
Andreopoulos, F.M., Beckman, E.J. and Russel, A.J., Biomaterials 18, 1343 (1998).CrossRefGoogle Scholar
Ling, J., Rong, M.Z., Zhang, M.Q., Polymer 53, 2691 (2012).CrossRefGoogle Scholar
Lendlein, A., Jiang, H., Jünger, O. and Langer, R., Nature 434, 879 (2005).CrossRefGoogle Scholar
Pilate, F., Mincheva, R., De Winter, J., Gerbaux, P., Wu, L., Todd, R., Raquez, J-M., Dubois, P., Chem. Mater. 26, 5860 (2014).CrossRefGoogle Scholar
Creed, D., Griffin, A.C., Gross, J.R.D., Heyle, C.E. and Venkataram, K., Mol. Cryst. Liq. Cryst. 155, 57 (1988).Google Scholar
Green, B.S., Lahav, M. and Schmidt, G.M.J., J. Chem. Soc. (B) 1971, 1552 (1971).Google Scholar
Andreopoulos, F.M., Beckman, E.J. and Russel, A.J., J. Polym. Sci. Part A: Polym. Chem. 38, 1466 (2000).3.0.CO;2-8>CrossRefGoogle Scholar
Utada, A.S., Chu, L.-Y., Fernandez-Nieves, A., Link, D.R., Holtze, C. and Weitz, D.A., MRS Bull. 32, 702 (2007).CrossRefGoogle Scholar
Poutaraud, A., Latouche, G., Martins, S., Meyer, S., Merdinoglu, D. and Cerovic, Z.G., J. Agric. Food Chem. 55, 4913 (2007).CrossRefGoogle Scholar
Takahashi, H., Sakuragi, M., Hasegawa, M. and Takahashi, H., J. Polym. Sci.: Part A-1 10, 1399 (1972).CrossRefGoogle Scholar
Kaiser, T., Grossi, L. and Fischer, H., Helv. Chim. Acta. 61, 223 (1978).CrossRefGoogle Scholar