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

Molecules

Felix B์hle²  Michael Hanack²  Thomas Ziegler¹ 

[1] Institute of Organic Chemistry, Universität Tübingen, Auf der Morgestelle 18, Tübingen 72076, Germany;

关键词: glycoconjugated phthalocyanine;    MEM;    CuAAC;   

DOI  :  10.3390/molecules201018367

来源: mdpi

【 摘 要 】

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 ε_max > 10⁵ m⁻¹ cm⁻¹ and absorption maxima λ > 680 nm, which make them attractive photosensitizers for photo-dynamic therapy.

【 授权许可】

CC BY   
© 2015 by the authors; licensee MDPI, Basel, Switzerland.