Journal
MOLECULES
Volume 20, Issue 10, Pages 18367-18386Publisher
MDPI
DOI: 10.3390/molecules201018367
Keywords
glycoconjugated phthalocyanine; MEM; CuAAC
Funding
- Buck-Stiftung
- Deutsche Forschungsgemeinschaft
- University of Tubingen
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In continuation of our work on glycoconjugated phthalocyanines, two new water soluble, non-ionic zinc(II) phthalocyanines have been prepared and fully characterized by means of H-1-NMR, C-13-NMR, MALDI-TOF, ESI-TOF, UV-Vis spectroscopy, emission spectroscopy and fluorescence lifetime measurements. The carbohydrate-containing phthalonitrile precursors were synthesized through a copper-catalyzed azide-alkyne cycloaddition (CuAAC). The 2-methoxyethoxymethyl protecting group (MEM) was used to protect the carbohydrate moieties. It resisted the harsh basic cyclotetramerization conditions and could be easily cleaved under mild acidic conditions. The glycoconjugated zinc(II) phthalocyanines described here have molar extinction coefficents epsilon(max) > 10(5) m(-1) cm(-1) and absorption maxima > 680 nm, which make them attractive photosensitizers for photo-dynamic therapy.
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