New amphiphilic platinum(II) phthalocyanine with peracetylated β-galactose moiety - Synthesis and photophysical properties

The synthesis of new glycoconjugated phthalonitrile connected with galactose moiety by triazole spacer via Cu (II)-mediated click reaction is reported. Reaction of azido derivatives of. beta-D-galactopyranose tetraacetate with 4-O-propargyloxy-substituted phthalonitrile in presence copper(II) sulfate pentahydrate and sodium L-ascorbate in tert-butanol/water gave desired glycophthalonitrile with 79% yield. Obtained phthalonitrile underwent mixed-cyclisation with the 4-tert-butyl-substituted phthalonitrile, to afford the mono-glycosylated platinum(II) phthalocyanine. Upon irradiation these compounds could sensitise the formation of singlet oxygen in acetone, with 0.90 quantum yield by method with use of 1,3-diphenylisobenzofuran (DPBF) as scavenger.

Automated summary

This study reports the synthesis of new glycoconjugated phthalonitrile connected with a galactose moiety via Cu (II)-mediated click reaction. The obtained compound can further react to form mono-glycosylated platinum(II) phthalocyanine, which can sensitize the formation of singlet oxygen under irradiation conditions.