Synthesis of Substituted Phthalocyanines with Bulky Substutients

Charles University in Prague, Faculty of Pharmacy in Hradec Králové Department of pharmaceutical chemistry and drug control Candidate Mgr. Ivana Zajícová Consultant Doc. PharmDr. Petr Zimčík Ph.D Title of Thesis Synthesis of substituted phthalocyanines with bulky substutients Synthesis of symmetric phthalocyanines and naphthalocyanines containing bulky substituent (tert- butylsulfanyl and later pentan-3-ylsulfanyl group) in their structure was aim of my master thesis. The precursors, 6,7-bis(tert-butylsulfanyl)naphthalene-2,3-dicarbonitrile and two 3,6-disubstituted phthalonitriles were prepared as starting materials. Synthesis of 3,4,12,13,21,22,30,31-octakis(tert- butylsulfanyl)naphthalocyaninato zinc(II) complex proceeded without any problems using diazabicycloundecene and zinc acetate in butanol. However, cyclotetramerization of precursor to octakis- 1,4,8,11,15,18,22,25-(tert-butylsulfanyl)phthalocyaninato zinc(II) complex was problematic. I could not find a suitable method of synthesis. As an alternative to this compound I tried to prepare analogue containing flexible pentane-3-ylsulfanyl instead of tert-butylsulfanyl group. In this case, a magnesium butoxide was used as initiator of cyclotetramerization. Magnesium complex was transformed to the zinc complex by removal of central magnesium..