Synthesis and characterization of new phthalocyanine compounds containingmixed-donor substituted macrocyclic groups

In this work, new phthalocyanine compounds containing mixed-donor substituted macrocyclic groups were synthesized . For this purpose, 2,2?-[1,1?-binafthalene-2,2?-diyl bis(oxy)]diethanol (1) was synthesized by the reaction of 1,1?-binafthalene-2,2?-diol with 2-chloroethanol. 6,7,22,23-tetrahydrobenzo[e]dinaphtho[1,2-m:2?,1?-k][1,4,7,10] tetraoxa cyclotetradecine-2,3-dicarbonitrile (2) was synthesized to get dinitrile derivative by the reaction of 2,2?-[1,1?-binafthalene-2,2?-diylbis(oxy)]diethanol (1) with 4,5-dichloro-1,2-dicyanobenzene.6,7,9,10,25,26,28,29-oktahydrobenzo[h]dinaphtho[1,2-s:2?,1?-?] [1,4,7,13, 16,7,10]tetraoxadithiacyloicosine-2,3-dicarbonitrile (7)was prepared under suitable reaction conditions by the reaction of 2,2?-[1,1?-binafthalene-2,2?-diylbis (oxy)]diethanol (1) with 1,2-bis-(2-iodoethylmercapto)-4,5-dicyanobenzene. The metal-free phthalocya- nine (3) by cyclotetramerization of dinitrile derivatives (2), was accomplished in dry n-pentanol at reflux temperature under nitrogen in a Schlenk tube. The complexes of metal phthalocyanine, cobalt (II) phthalocyanines (4) and (8), copper (II) phthalocyanines (5) and (9), zinc (II) phthalocyanine (6), nickel (II) phthalocyanine (10); were prepared by the reaction of (2) and (7) to get dinitrile derivative complexes by order of the , anhydrous zinc (II) acetate, anhydrous copper (II) chloride, anhydrous cobalt (II) chloride, anhydrous nickel (II) chloride salts and 2-(dimethylamino)ethanol (DMAE) by using microwave have been synthesized. The structures of all these original compounds were idendified by using, elemental analysis, 1H-NMR, 13C-NMR, IR, mass and UV-vis spectrocopic data.