Helical Self-Assembly of Optically Active Glycoconjugated Phthalocyanine J-Aggregates

Abstract

Four galactoconjugated zinc(II) phthalocyanines (Pcs) have been prepared and fully characterized. The carbohydrate-containing phthalonitrile precursors of the Pcs were synthesized through a copper-catalysed azide-alkyne cycloaddition (CuAAC). The Pcs show a remarkable aggregation behaviour in solution, depending on the nature of the solvent, the temperature and the substitution position on the phthalocyanine. Solvent-dependent CD-spectroscopy experiments show that these Pcs aggregate as chiral helices in solution. Crystal structure data of a phthalocyanine bearing two carbohydrate units substantiate the properties shown by CD spectroscopy. Furthermore, the 1,2,3-triazole moieties of the Pcs play a decisive role in the formation of supramolecular aggregates. The glycoconjugated zinc(II) phthalocyanines described here show molar extinction coefficients ϵmax>105 M−1 cm−1 and absorption maxima λmax>680 nm, which make them attractive photosensitizers for Photodynamic Therapy (PDT).