Synthesis and characterisation of a selection of phthalocyanines covalently bonded to water-soluble polymers and a ferrocenyl fragment

[摘要] English: This thesis is concerned with the synthesis of phthalocyanine derivatives and their anchoring ontowater-soluble polyaspartamides to produce compounds that may have biomedical applications,especially in the photodynamic therapy of cancer. The anchoring of a ferrocenyl fragment, whichitself is an anti-neoplastic entity, onto both the polymer and a phthalocyanine entity was alsoaccomplished utilizing biodegradable amide bonds. The electrochemical behaviour of selectedphthalocyanines and polymer-anchored phthalocyanines is reported.Phthalocyanines containing both amine and carboxylic acid functional groups were prepared usingestablished methods. The active amine side chains of the polymers derived from aspartic acidand/or lysine were utilized to couple both ferrocenyl and phthalocyanine entities. In additionferrocenylethylamine was anchored onto a phthalocyanine containing carboxylic acid groups. Thephthalocyanine-anchored polymers showed a marked decrease in water-solubility especially whenthese had additional ferrocenyl fragments anchored onto either the polymeric backbone or onto apolymer-bound phthalocyanine.The attachment of a ferrocenylethylamine onto a polymer-bound phthalocyanine containing threefree carboxylic acid groups appears to be a sterically hindered process as only one of the carboxylicacid groups undergoes ami dation even in the presence of excess amine.

[发布机构] University of the Free State