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Helical Self‐Assembly of Optically Active Glycoconjugated Phthalocyanine J ‐Aggregates
Author(s) -
Bächle Felix,
MaichleMössmer Cäcilia,
Ziegler Thomas
Publication year - 2019
Publication title -
chempluschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.801
H-Index - 61
ISSN - 2192-6506
DOI - 10.1002/cplu.201900381
Subject(s) - phthalocyanine , chemistry , supramolecular chemistry , phthalonitrile , zinc , photochemistry , j aggregate , solvent , spectroscopy , cycloaddition , organic chemistry , crystal structure , molecule , catalysis , physics , quantum mechanics
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 ϵ max >10 5 M −1 cm −1 and absorption maxima λ max >680 nm, which make them attractive photosensitizers for Photodynamic Therapy (PDT).