Synthesis and characterization of new metal-free and metallophthalocyanines containing macrobicyclic moieties

The synthesis and characterization of novel metal-free and cobalt phthalocyanine, peripherally symmetrically derived from 2,3,6,7,10,11,13,14-octahydro-5H,9H-4,12-(propanothiopropano)-1,8,15,23,4,12-benzotetrathiodiazacycloheptadecane-17,18-dicarbonitrile (4) which was prepared by the reaction of 1,9-diaza-5,13-dithiocyclohexadecane (3) and 1,2-bis(2-iodoethylmercapto)-4,5-dicyanobenzene (2) was carried out. The novel compounds were characterized by using elemental analysis, 1H, 13C NMR, IR, UV–vis and MS techniques.

Graphical abstractNew metal-free phthalocyanine (H2Pc) and cobalt phthalocyanine (CoPc) containing four peripheral mixed donor macrobicyclic moieties has been prepared by a cyclotetramerisation reaction of macrobicyclic dinitrile (4).Figure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Different synthetic approaches concerning (2) was investigated and the novel route was found. ► The synthesis of compound (4) containing N2S4 macrobicyclic moiety has been accomplished. ► Novel phthalocyanines bearing peripheral N2S4 macrobicyclic moieties were synthesized.