Synthesis of Porphyrins β-Tetrasubstituted by Flexible Hydrocarbon Chains

The free base 2,4-bis-(1′-dodecynyl)-deuteroporphyrin IX dioctylester, 6a, its Zn(II)complex, Zn-6a, its Cu(II)complex, Cu-6a, its Ni(II)complex, Ni-6a and a number of related compounds have been prepared. The synthesis of 6a involves as key steps the palladium-catalyzed coupling of β-diiodoporphyrin with dodecyne, and the acid-catalyzed esterification of the two propionic acid groups of deuteroporphyrin with n-octanol.