title: Synthesis and Spectroscopic Evaluation of Two Novel Glycosylated Zinc(II)-Phthalocyanines.
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.
authors.affiliation: Institute of Organic Chemistry, Universität Tübingen, Auf der Morgestelle 18, Tübingen 72076, Germany. felix.baechle@uni-tuebingen.de.
authors.forename: Felix
authors.initials: F
authors.lastname: Bächle
authors.affiliation: Institute of Organic Chemistry, Universität Tübingen, Auf der Morgestelle 18, Tübingen 72076, Germany. hanack@uni-tuebingen.de.
authors.forename: Michael
authors.initials: M
authors.lastname: Hanack
authors.affiliation: Institute of Organic Chemistry, Universität Tübingen, Auf der Morgestelle 18, Tübingen 72076, Germany. thomas.ziegler@uni-tuebingen.de.
authors.forename: Thomas
authors.initials: T
authors.lastname: Ziegler
mesh_terms: D000480:Alkynes / Q000737:chemistry; D001386:Azides / Q000737:chemistry; D002384:Catalysis; D002413:Cations, Divalent; D056831:Coordination Complexes / Q000138:chemical synthesis / Q000737:chemistry*; D003300:Copper / Q000737:chemistry; D061565:Cycloaddition Reaction; D006001:Glycoconjugates / Q000138:chemical synthesis / Q000737:chemistry*; D006031:Glycosylation; D007211:Indoles / Q000737:chemistry*; D054833:Isoindoles; D009682:Magnetic Resonance Spectroscopy; D009570:Nitriles / Q000737:chemistry; D017319:Photosensitizing Agents / Q000138:chemical synthesis / Q000737:chemistry*; D012995:Solubility; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; D014867:Water / Q000737:chemistry; D015032:Zinc / Q000737:chemistry*
chemical_list: D000480:Alkynes; D001386:Azides; D002413:Cations, Divalent; D056831:Coordination Complexes; D006001:Glycoconjugates; D007211:Indoles; D054833:Isoindoles; D009570:Nitriles; D017319:Photosensitizing Agents; D014867:Water; D003300:Copper; D015032:Zinc; C013647:phthalocyanine
keywords: CuAAC; MEM; glycoconjugated phthalocyanine