Przemysl Chemiczny, Vol.94, No.5, 781-783, 2015
Synthesis and characterization of a purine-phthalocyanine conjugate as a potential photosensitizer
6-Methylthiopurine was substituted at the N9 position with BrCH2CH2OH in HCONMe2 at 65 degrees C and etherified with 3-nitrophthalonitrile in Me2SO at 40 degrees C. The phthalonitrile derivative and 3,6-bis[3-(ethoxycarbonyl)propoxy]-1,2-benzenedicarbonitrile were subjected to the macrocyclization in presence of 1,8-diazabicyclo[5.4.0]undec-7-ene and Zn(OAc)(2) in n-pentanol at 110 degrees C to yield a green zinc(II) {1,4,8,11,15,18-hexakis-bis[3-(pentoxycarbonyl)propoxy]-22-[1,9-dihydro-6H-purin-6-on-9-yl)ethoxy]phthalocyanine pigment and a known zinc(II){1,4,8,11,15,18,22,25-octakis[(3-pentoxycarbonyl)propoxyl phthalocyanine as a by-product. The purine-phthalocyanine conjugate was characterized by mass spectrometry, UV-VIS spectroscopy and various NMR techniques.