The new metal-free, zinc, magnesium, indium ball-type phthalocyanines and their hybrids with graphene oxide: Synthesis, investigation of photophysical, photochemical properties and theoretical studies

Abstract

In this study, four ball-type phthalocyanines (BTPc-H2-4, BTPc-Zn-5, BTPc-Mg-6, BTPc-In-7) were synthesized from 3,3 ',((3,5-di-tert-butyl-1,2-phenylene)bis(oxy)diphthalonitrile in a single reaction step. Non-covalent balltype phthalocyanine (BTPc)-graphene oxide (GO) hybrids (BTPc-GO) were prepared by simple sonication method. The structures were confirmed by elemental analysis, ultraviolet-visible (UV-Vis), fourier-transform infrared (FT-IR), proton nuclear magnetic resonance (1H NMR), MALDI-TOF MS spectroscopies, elemental analysis and scanning electron microscope (SEM). The photophysical and photochemical properties of ball-type phthalocyanines were investigated in dimethyl sulfoxide (DMSO) and tetrahydrofuran (THF). In this way, the contribution of solution polarity to these properties was compared. The contribution of GO was examined by examining the singlet oxygen quantum yields of BTPc-GO hybrids in DMSO. In addition, the structural properties of ball-type phthalocyanines were examined through theoretical studies and the effect of structural properties on experimentally determined band gaps was examined. Interestingly, we also report that ball-type thalocyanines are both photostable and exhibit extremely high singlet oxygen quantum yields. In addition, we can state that hybrids of these compounds with GO also show the ability to increase the singlet oxygen quantum yield, depending on the degree of interaction.