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

[Display omitted] 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. β-d-galactopyranose tetraacetate with 4-O-propargyloxy-substituted phthalonitrile in presence cop...

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Bibliographic Details
Published in:Polyhedron 2021-09, Vol.206, p.115331, Article 115331
Main Authors: Volov, Alexander N., Volov, Nikolai A., Burtsev, Ivan D.
Format: Article
Language:English
Subjects:
Click reaction
Glycophthalocyanines
Glycophthalonitriles
Photodynamic therapy
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Summary:[Display omitted] 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. β-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.
ISSN:0277-5387
DOI:10.1016/j.poly.2021.115331