In the present paper, the syntheses, spectroscopic characterization, aggregation behaviours and photocatalytic properties of phthalocyanine compounds were searched. Octa-substituted phthalocyanines (Zn-II (Pc-Zn), Mg-II (Pc-Mg) and Pb-II (Pc-Pb)) with eight peripheral (E)-3-(3-hydroxyphenyl)-1-(2,4,5-trimethoxyphenyl)prop-2-en-1-one groups were synthesized by cyclotetramerization. The spectral properties of these compounds were carried out that used widespread spectroscopic techniques. Later on, aggregation properties of synthesized phthalocyanines were examined in polar and apolar solvents. In addition to this, the photocatalytic activities of new synthesized metallophthalocyanines containing various central metal ions (zinc (II), magnesium (II) and lead (II)) were investigated. Three different metal centered phthalocyanines have been prepared for the photodegradation of 4-nitrophenol. In the photodegradation reactions that carried out in the photoreactor for 1 h without using any oxidant, 4-nitrophenol compound was completed with 90% (for Pb-II (Pc-Pb)), 56% (for Zn-II (Pc-Zn)) and 12% (for Mg-II (Pc-Mg)) conversion from toxic species to non-harmful species and unknown intermediates. The turnover numbers were determined as 1500 for Pb-II (Pc-Pb), 933 for Zn-II (Pc-Zn).