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Synthesis and solution studies on azaphthalocyanines with quaternary aminoethyl substituents
Author(s) -
Uslu Kobak Rabia Z,
Gül Ahmet
Publication year - 2009
Publication title -
coloration technology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.297
H-Index - 49
eISSN - 1478-4408
pISSN - 1472-3581
DOI - 10.1111/j.1478-4408.2008.00171.x
Subject(s) - chemistry , magnesium , trifluoroacetic acid , derivative (finance) , metal , inorganic chemistry , metal ions in aqueous solution , hydrochloride , methyl iodide , iodide , transition metal , ultraviolet , medicinal chemistry , organic chemistry , catalysis , physics , quantum mechanics , financial economics , economics
A pyrazinedinitrile derivative carrying dimethylaminoethylsulphanyl groups at positions 5 and 6 was synthesised from 2‐dimethylaminoethanethiol hydrochloride and 2,3‐dicarbonitrile‐5,6‐dichloropyrazine. The dicarbonitrile gave magnesium azaphthalocyanine (MgAzaPc) when reacted with magnesium propoxide in propanol. The conversion of the MgAzaPc to a metal‐free derivative was achieved by treatment with trifluoroacetic acid. Incorporation of transition metal ions into the inner core of azaphthalocyanine was accomplished by treatment of the metal‐free derivative with metal acetates, i.e. Zn(OAc) 2 , Co(OAc) 2 . These azaphthalocyanines were converted into water‐soluble quaternised products by reaction with methyl iodide. Aggregation phenomena were followed for magnesium azaphthalocyanine with quaternisable dimethylamino substituents within a specific range of pH. The compounds were characterised by Fourier transform–infrared, proton nuclear magnetic resonance, mass and ultraviolet–visible spectral data.