Synthesis and solution studies on azaphthalocyanines with quaternary aminoethyl substituents

Kobak R. Z., GUEL A.

COLORATION TECHNOLOGY, vol.125, no.1, pp.22-28, 2009 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 125 Issue: 1
  • Publication Date: 2009
  • Doi Number: 10.1111/j.1478-4408.2008.00171.x
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.22-28
  • Istanbul Technical University Affiliated: Yes


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.