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First Generation and Trapping of a Dehydrometallophthalocyanine Starting from Triazole‐Functionalized Zinc Phthalocyanine
Author(s) -
Vagin Sergei I.,
Frickenschmidt Antje,
Kammerer Bernd,
Hanack Michael
Publication year - 2005
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200500705
Subject(s) - zinc , chemistry , adduct , phthalocyanine , anthracene , mass spectrometry , amination , combinatorial chemistry , derivative (finance) , spectroscopy , furan , elemental analysis , photochemistry , organic chemistry , catalysis , physics , chromatography , quantum mechanics , financial economics , economics
Direct 1 N ‐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 1 H and 13 C‐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.