Synthesis of 4-methylthiophenyl silicon phthalocyanines axially substituted with carboxylic acids for MOF materials

Abstract

Two new peripherally substituted with 4 and 8 electron-donating 4-methylthiophenyl silicon phthalocyanines, (ArS)4SiPc 1 and (ArS)8SiPc 2, axially substituted with carboxylic acids have been synthesized using microwave irradiation in a very good yield. The new compounds have been characterized by 1H-NMR, UV-vis, fluorescence, differential pulse voltammograms, and HR-MALDI-TOF mass spectrometry. An study of the stability of the axial chlorinated SiPcs in the function of the number of thiophenyl substituents indicates than (ArS)8SiPcCl2 10 degradates faster, to its corresponding unreactive dihydrosilicon phthalocyanine derivative (ArS)8SiPc(OH)2 11, than (ArS)4SiPcCl2. The new SiPcs are excellent candidates as photoactive linkers for the construction of MOF materials.