Synthesis and characterization of novel 5-monocarbohydrate-10,20-bis-aryl-porphyrins

Abstract

The synthesis of derivatives bearing glucose or galactose units linked by an acrylate spacer to one free meso position of a bis-aryl-porphyrin macrocycle was developed and characterized by standard spectroscopic techniques. The new mono-substituted gluco- and galacto-porphyrin derivatives 5–8 present an alternative to the widespread tetra-aryl porphyrin functionalization. Singlet oxygen studies showed a comparable singlet oxygen production with TPP. Furthermore, the less bulky architectures here synthesized present an opportunity to enhance the PDT and PDI capabilities of glycoporphyrins with a simple synthetic modification at one of the meso positions.