Red manganese phthalocyanines from highly hindered hexadecaalkoxyphthalocyanines

Highly hindered magnesium and metal-free green 1,2,3,4,8,9,10,11,15,16,17,18,22,23,24,25-hexadecaneopentoxyphthalocyanine and 1,2,3,4,8,9,10,11,15,16,17,18,22,23,24,25-hexadeca(cyclohexylmethyloxy)phthalocyanine were prepared via magnesium 1-octanolate and 3,4,5,6-tetraneopentoxyphthalonitrile or 3,4,5,6-tetra(cyclohexylmethyloxy)phthalonitrile. Treatment of the metal-free phthalocyanine with Mn(OAc)2 yielded deep red manganese(III) hexadecaalkoxy phthalocyanines. Electrochemical and spectroelectrochemical studies led to the characterization, in solution, of a series of species in a range of different manganese and phthalocyanine oxidation states.

Graphical abstractHighly hindered magnesium and metal-free green 1,2,3,4,8,9,10,11,15,16,17,18,22,23,24,25-hexadecaneopentoxyphthalocyanine and 1,2,3,4,8,9,10,11,15,16,17,18,22,23,24,25-hexadeca(cyclohexylmethyloxy)phthalocyanine were prepared via magnesium 1-octanolate and 3,4,5,6-tetraneopentoxyphthalonitrile or 3,4,5,6-tetra(cyclohexylmethyloxy)phthalonitrile. Treatment of the metal-free phthalocyanine with Mn(OAc)2 yielded deep red manganese(III) hexadecaalkoxy phthalocyanines. Electrochemical and spectroelectrochemical studies led to the characterization, in solution, of a series of species in a range of different manganese and phthalocyanine oxidation states.Figure optionsDownload full-size imageDownload as PowerPoint slide