Synthesis of a naphthalocyanine-like dye: The first report on Zn(II)-1,6-methano[10]annulenecyanine

Abstract

The synthesis of the new dye 1,6-methano[10]annulenecyanine is described. For this purpose, the 3,4-dicyano-1,6-methano[10]annulene and 3,4-carboxyimide-1,6-methano[10]annulene buildings blocks were synthesized in six to eight steps. In both cases, these building blocks were then cyclotetramerized to furnish a new Zn(II)-1,6-methano[10]annulenecyanine which presents a strong red-shifted absorption band at 800 nm and high solubility in common organic solvents.