Synthesis and solution studies on azaphthalocyanines with quaternary aminoethyl substituents

Autor: Ahmet Gül, Rabia Zeynep Uslu Kobak
Rok vydání: 2009
Předmět:
Zdroj: Coloration Technology. 125:22-28
ISSN: 1478-4408
1472-3581
DOI: 10.1111/j.1478-4408.2008.00171.x
Popis: 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.
Databáze: OpenAIRE