The effect of irradiation by ultraviolet light on ureido‐pyrimidinone based biomaterials |
| |
| Authors: | Björne B. Mollet Yoko Nakano Pieter C. M. M. Magusin A. J. H. Spiering Jef A. J. M. Vekemans Patricia Y. W. Dankers E. W. Meijer |
| |
| Affiliation: | 1. Institute for Complex Molecular Systems, Eindhoven University of Technology, The Netherlands;2. Laboratory for Chemical Biology, Department of Biomedical Engineering, Eindhoven University of Technology, The Netherlands;3. Department of Chemistry, University of Cambridge, United Kingdom;4. Laboratory of Macromolecular and Organic Chemistry, Department of Chemical Engineering and Chemistry, Eindhoven University of Technology, The Netherlands |
| |
| Abstract: | Supramolecular polymers based on ureido‐pyrimidinone (UPy) represent a promising class of biocompatible materials for medical applications. Here, the chemical modification effect of UV irradiation, used to sterilize these materials, is studied. Besides anticipated crosslinking effects, UV irradiation causes telechelic UPy‐polymers to become fluorescent. UPy‐model compounds confirm a relation between UV‐induced changes and the UPy‐moiety. UV‐induced fluorescence and IR‐spectral changes are (partially) reversible by heat and/or solvent treatment. The results indicate the presence of at least two distinct UV‐induced molecular species. UPy‐model compounds with specific tautomeric forms directly relate fluorescence to UPy‐enol tautomers. Photo‐enolization is hypothesized to occur via an excited‐state intermolecular double proton transfer. Changes in UPy‐tautomeric equilibrium and crosslinking are factors that influence the dynamics of UPy‐based materials. Identification and understanding of such factors will aid in the successful application of these materials, for example as biomaterial in tissue engineering applications. © 2015 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2016 , 54, 81–90 |
| |
| Keywords: | biomaterials crosslinking fluorescence FT‐IR irradiation photoreactive effects supramolecular structures tautomerization ureido‐pyrimidinone |
|
|
