New glycosylated platinum(II) phthalocyanine containing ribose moiety -synthesis and photophysical properties

The synthesis and spectral characterisation of new glycoconjugated phthalonitrile connected with triazole linker via Cu(II)-mediated click reaction is reported. Treatment of azido derivative of 1-methoxy-2,3- O-isopropylidene-beta-D-ribose with 4-O-propargyloxy-substituted phthalonitrile in presence copper(II) sulfate pentahydrate and sodium L-ascorbate in tert-butanol/water gave desired glycophthalonitrile with 84% yield. This precursor underwent mixed-cyclisation with the tert-butyl-substituted phthalonitrile, to afford the mono-glycosylated A3B-type platinum(II) phthalocyanine. Upon irradiation this compound could sensitise the formation of singlet oxygen in acetone, with 0.95 quantum yield by comparative method with use of 1,3-diphenylisobenzofuran (DPBF) as scavenger. (C) 2020 Elsevier B.V. All rights reserved.