Add time:07/17/2019         Source:sciencedirect.com

Two chlorin derivatives bearing (trifluoromethyl)phenyl substituents at meso positions were synthesized via 1,3-dipolar cycloaddition. These pyrrolidine-fused chlorins are characterized by 1H, 13C NMR spectroscopy, mass spectrometry, UV-Vis absorption and fluorescence spectroscopy. The obtained compounds revealed UV-Vis spectra typical of chlorins. Fluorescence quantum yields were calculated to be ca. 0.2 and ca. 0.3 in DMF and DMSO, respectively, for both compounds. The chlorin bearing 3,5-bis(trifluoro-methyl)phenyl substituent in meso positions (0.69 in DMF, 0.57 in DMSO) revealed a stronger singlet oxygen formation ability than that with 4-(trifluoromethyl)phenyl moieties (0.50 in DMF, 0.45 in DMSO). Both compounds were found to be stable under irradiation in DMF. Nevertheless, irradiation of both compounds in DMSO solution caused their phototransformation. As the studied compounds are insoluble in aqueous media, they were incorporated in lipid vesicles. Photodynamic bacteria inactivation experiments showed log reduction of bacterial growth for Enterococcus faecalis at 4.84; Staphylococcus aureus at 4.09; Escherichia coli at 2.23. No activity of both macrocycles was noticed against Pseudomonas aeruginosa and fungi: Candida albicans and Trichophyton mentagrophytes.

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