Derivatization and in situ metallation of phthalocyanines using click chemistry

Dialkyl (3,4-dicyanophenyl)propargylmalonates were prepared by the reaction of propargyl bromide and the potassium salt of dialkyl-3,4-dicyanophenylmalonates. A cyclotetramerization reaction was achieved in pentanol in the presence of DBU without protective/deprotective chemistry, affording the peripherally tetrasubstituted alkynyl phthalocyanines. Subsequently, in situ metallation and ‘clicking’ were employed for the first time as an efficient and quantitative route to tetratriazole-functionalized phthalocyanines.

Graphical abstractAlkynyl phthalocyanines were synthesized without protective/deprotective chemistry. Subsequently, in situ metallation and ‘clicking’ were employed for the first time as an efficient and quantitative route to tetratriazole-functionalized phthalocyanines.Figure optionsDownload full-size imageDownload as PowerPoint slide