Synthesis and characterization of novel silane derivatives of phenothiazinium photosensitisers

Abstract

Phenothiazine based dyes are widely explored dyes for their antibacterial and photosensitising applications. Despite their amazing optical and photosensitising (theranostic) properties, their usage in nanomedicine is very low compared to other organic dyes. This is due to the lack of reactive functional groups for encapsulating them into metal oxide nanoparticles. This work describes the synthesis of three different phenothiazinium alkoxysilane derivatives by oxidative amination of 10H-phenothiazine using amino alkoxysilanes. The new derivatives were characterized using NMR, FT-IR, DSC/TGA, and mass spectral studies. Optical and photosensitising properties (absorption spectrum, photostability, and singlet oxygen quantum yield) of the silane derivatives were investigated using UV–Visible spectroscopy. These compounds are suitable for conjugation with silica in the sol-gel synthesis of silica nanoparticles and silica surface coaters, which will reduce dye leakage and improve the dye efficacy in the treatment of cancer and light activated antimicrobial surfaces.