- 4 Downloads
Nucleophilic substitution of fluorine atoms in the phenyl rings by alkoxy groups was performed in perfluorosubstituted zinc(II) octaphenylporphyrazine [ZnPAF40]. Up to 12 fluorine atoms are substituted in the reaction with sodium butoxide in boiling butanol leading to the formation of [ZnPAF40-n(OBu)n] (n = 6–12). Up to eight monosaccharide groups are introduced in the reaction with 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose (Gal´) in toluene in the presence of sodium hydride leading to the formation of [ZnPaF(40-n)(Gal´)n] (n = 6–8). It was possible to obtain a water-soluble glycoconjugated zinc(II) porphyrazine [ZnPaF(40-n)(Gal)n] after removal of the isopropylidene protecting groups by treatment with trifluoroacetic acid. Substitution products are characterized by electron absorption spectroscopy, NMR spectroscopy, and mass spectrometry. Substituting the fluorine atoms with monosaccharide residues leads to an increase in the fluorescence quantum yield from ФF = 0.19 for [ZnPAF40] to 0.29 for [ZnPA(Gal´)nF40-n] (n = 6–8).
Key wordsperfluorinated porphyrazines nucleophilic aromatic substitution galactose water soluble porphyrazines
Unable to display preview. Download preview PDF.
- 2.S. G. DiMagno, J. C. Biffinger, H. Sun, in Fluorine in Heterocyc lic Chemistry, Ed. V. G. Nenajdenko, Vol. 1, 5-Membered Heterocycles and Macrocycles, Springer, Heidel berg, 2014, p. 589–620.Google Scholar
- 3.P. A. Stuzhin, in Fluorine in Heterocyclic Chemistry, Ed. V. G. Nenajdenko, Vol. 1, 5-Membered Heterocycles and Macrocycles, Springer, Heidelberg, 2014, p. 621–681.Google Scholar
- 4.T. Goslinski, J. Piskorz, Photochem. Photobiol., 2011, 304.Google Scholar