Sprecher
Beschreibung
Synthesis and investigation of Nile Red- and aurone-labeled methacrylate derivatives as novel solvatochromic probes for polymer analysis
Sören Steup1, Jonah Decker2, Sergey I. Druzhinin2, Daria V. Berdnikova1, Holger Schönherr2, Heiko Ihmels1*
1 Organic Chemistry II, Department of Chemistry and Biology and Research Center of Micro and Nanochemistry and (Bio)Technology (Cμ), University of Siegen
2 Physical Chemistry I, Department of Chemistry and Biology and Research Center of Micro and Nanochemistry and (Bio)Technology (Cμ), University of Siegen
Fluorosolvatochromic dyes are known for their ability to change their emission properties in response to the polarity of respective solvent, thus providing valuable insight into local polarity and dynamics of the surrounding solvent shell. In this context, Nile Red is widely used as solvatochromic dye in cell biology, for example, to detect and characterize membranes.[1] Likewise, it may be applied for the fluorimetric analysis of polymers brushes. For this purpose, however, it has to be covalently incorporated into the polymers, which may be accomplished by the attachment to the corresponding monomer units.
In this study, we present the functionalization of methacrylate monomers with Nile Red and selected aurone derivatives. Specifically, we investigated the properties of the resulting dye conjugates for the application as solvatochromic probes for the detection of local polarity and mobility of the environment, both as monomer and when incorporated into a polymer. In particular, the aurones proved to be a valuable fluorophore because of their properties as dual-state emission (DSE) fluorophores.[2]
Literature:
[1] G. Ballarin, M. Biasiotto, A. Reisbitzer, M. Hegels, M. Bolte, S. Krauß, D. V. Berdnikova, RSC Med. Chem. 2024, 15, 3092.
[2] D. V. Berdnikova, S. Steup, M. Bolte, M. Suta, Chem. Eur. J. 2023, 29, e202300356.