Simple One-pot Synthesis of Triazine-porphyrins

A series of substituted triazine-tetraphenylporphyrins were synthesized from the reaction of 5-[4-(3,5-dichloro-triazine-1-oxygen)] phenyl-10,15,20-triphenylporphyrin with amines or alcohols. A new simple one-pot synthetic method from the reaction of the tetraphenylporphyrin with hydroxyl group and 2,4,6-trichloro-1,3,5-triazine and other nucleophiles was studied. The researches show that amines or alcohols substitute selectively the one of two chlorine atoms in 5-[4-(3 5-dichloro-triazine-1-oxygen)] phenyl-10, 15 20-triphenylporphyrin under different conditions to yield the substituted triazine-tetraphenylporphyrins. The structures of the substituted triazine-tetraphenylporphyrins depend on the nucleophilicity, stereochemistry of the nucleophiles and the reaction temperatures. Seven new triazine-porphyrin compounds were synthesized from the reaction of 5-(4-hydroxyl) phenyl-10, 15 20-triphenylporphyrin with 2,4,6-trichlorotriazine, amines or alcohols. Their structures were charactered with H-1 NMR, MS, UV-Vis and elemental analysis.