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Synthesis of phthalocyanines with one sulfonic acid, carboxylic acid, or amino group
Author(s) -
Kliesch Holger,
Weitemeyer Andrea,
Müller Silke,
Wöhrle Dieter
Publication year - 1995
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.1995199507168
Subject(s) - chemistry , sulfonic acid , zinc , group (periodic table) , amino acid , lithium (medication) , glycine , nuclear magnetic resonance spectroscopy , polymer chemistry , stereochemistry , medicinal chemistry , organic chemistry , biochemistry , medicine , endocrinology
Monofunctional phthalocyanines 7a,b , one bearing a sulfo and the other one a carboxyl group, were synthesized by lithium alkoxyde‐catalyzed statistical tetramerization of 4‐(4‐ tert ‐butylphenoxy)‐1,2‐benzenedicarbonitrile ( 3c ) with 1,2‐dicyanobenzenes 3a,b carrying a carboxyl or sulfo group. Tribenzonaphthoporphyrazines 9a,b with one carboxyl or amino group were prepared under similar reaction conditions by tetramerization of 3,6‐dihexyloxy‐1,2‐benzenedicar‐bonitrile with 6‐amino‐ or 6‐carboxy‐2,3‐naphthalenedicar‐bonitrile 6b,6a . The zinc(II)‐containing macrocycles 7a, b, 9a, b obtained in yields of 11–20% were purified by column chromatography and characterized by UV/Vis, mass, and 1 H‐NMR spectroscopy.