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Molecules 2015, 20(10), 18367-18386; doi:10.3390/molecules201018367

Synthesis and Spectroscopic Evaluation of Two Novel Glycosylated Zinc(II)-Phthalocyanines

Institute of Organic Chemistry, Universität Tübingen, Auf der Morgestelle 18, Tübingen 72076, Germany
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Author to whom correspondence should be addressed.
Academic Editor: Giuseppe Mele
Received: 23 September 2015 / Revised: 5 October 2015 / Accepted: 6 October 2015 / Published: 9 October 2015
(This article belongs to the Special Issue Tetrapyrroles, Porphyrins and Phthalocyanines)
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Abstract

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 1H-NMR, 13C-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 εmax > 105 m−1 cm−1 and absorption maxima λ > 680 nm, which make them attractive photosensitizers for photo-dynamic therapy. View Full-Text
Keywords: glycoconjugated phthalocyanine; MEM; CuAAC glycoconjugated phthalocyanine; MEM; CuAAC
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Bächle, F.; Hanack, M.; Ziegler, T. Synthesis and Spectroscopic Evaluation of Two Novel Glycosylated Zinc(II)-Phthalocyanines. Molecules 2015, 20, 18367-18386.

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