Synthesis and characterization of new metal-free and nickel(II) phthalocyanines containing hexaazadioxa macrobicyclic moieties

Abstract

Novel symmetrically tetrasubstituted metal-free and metallophthalocyanines (5) and (6) which contain four hexaazadioxamacrobicycles on peripheral positions, have been synthesized. Macrobicyclic compound 3 and has been prepared by reaction of (1,3,6,9,11,14- hexaazatricyclo[12.2.1.1^6,9])octadecane (1) with 1,2-bis(2-iodoethoxy)-4,5-dibromobenzene (2). Compound 4 has been synthesized by reaction of compound 3 with CuCN in dry DMF. The target symmetrical phthalocyanines were separated by column chromatography and characterized by elemental analyses, ¹H, ¹³C–NMR, IR, UV–Visible and FAB mass spectroscopies.

Keywords:

• Phthalocyanines
• Macrobicycles
• Metallophthalocyanines
• Mixed-donors

Acknowledgement

This work was supported by the Research Fund of Karadeniz Technical University (Trabzon, Turkey), Project Number: 2002.111.2.6.