First generation and trapping of a dehydrometallophthalocyanine starting from triazole-functionalized zinc phthalocyanine.
Direct 1N-amination of the triazole-fused zinc phthalocyanine 2 and oxidation of the formed amino derivative 3 resulted in the generation of the very reactive intermediate, the dehydrometallophthalocyanine 4, which was not known previously. The latter was trapped in situ with different dienes, for example, furan, tetraphenylcyclopentadienone, and anthracene to form the corresponding Diels-Alder adducts. The products were characterized by 1H and 13C-dept135 NMR, and UV/Vis spectroscopy, MALDI-TOF mass spectrometry, and elemental analysis, which are fully in agreement with their structure. The developed synthetic procedure opens a simple and versatile pathway towards unsymmetrical peripheral modification of phthalocyanines, which is readily applicable to the micromol scale and is important for the design of new interesting Pc-based systems.
Vagin
Sergei I
SI
Institut für Organische Chemie, Universität Tübingen, Auf der Morgenstelle 18, 72076 Tübingen, Germany.
Frickenschmidt
Antje
A
Kammerer
Bernd
B
Hanack
Michael
M
D007211:Indoles / Q000737:chemistry*; D054833:Isoindoles; D009682:Magnetic Resonance Spectroscopy / Q000379:methods / Q000592:standards; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D010084:Oxidation-Reduction; D012015:Reference Standards; D014230:Triazoles / Q000737:chemistry*; D015032:Zinc / Q000737:chemistry*
D007211:Indoles; D054833:Isoindoles; D009942:Organometallic Compounds; D014230:Triazoles; D015032:Zinc; C013647:phthalocyanine