Nipagin-Functionalized Porphyrazine and Phthalocyanine—Synthesis, Physicochemical Characterization and Toxicity Study after Deposition on Titanium Dioxide Nanoparticles P25

Abstract

Aza-porphyrinoids exhibit distinct spectral properties in UV-Vis, and they are studied in applications such as photosensitizers in medicine and catalysts in technology. The use of appropriate peripheral substituents allows the modulation of their physicochemical properties. Phthalocyanine and sulfanyl porphyrazine octa-substituted with 4-(butoxycarbonyl)phenyloxy moieties were synthesized and characterized using UV-Vis and NMR spectroscopy, as well as mass spectrometry. A comparison of porphyrazine with phthalocyanine aza-porphyrinoids revealed that phthalocyanine macrocycle exhibits higher singlet oxygen generation quantum yields, reaching the value of 0.29 in DMF. After both macrocycles had been deposited on titanium dioxide nanoparticles P25, the cytotoxicities and photocytotoxicities of the prepared materials were studied using a Microtox® acute toxicity test. The highest cytotoxicity occurred after irradiation with a red light for the material composed of phthalocyanine deposited on titania nanoparticles.

Synthesis, Electrochemical and Photochemical Properties of Sulfanyl Porphyrazine with Ferrocenyl Substituents

“…The fluorescence studies performed for the DMF and DMSO solutions of Pz 4 did not reveal any emission properties. The literature data indicated that emission quenching by sulfur atoms combined with the porphyrazine core could be a reason for the lack of fluorescence [ 29 , 30 ].…”

Titanium Dioxide-Based Photocatalysts for Degradation of Emerging Contaminants including Pharmaceutical Pollutants

“…The hybrid material was photocatalytically active and degradation of both substances was noted after irradiation with red light for 8 min [165]. In another study with nipagin-functionalized porphyrazines, phthalocyanines, and P25 TiO 2 , fluorescence and singlet oxygen quantum yields as well as photostability were assessed [166]. The measurements were conducted based on the reduction in DPBF in DMF and DMSO after irradiation with red light (665 nm).…”

“…The materials showed considerable dark toxicity-up to 80% decrease in cell viability, reaching nearly 100% after irradiation of the samples with red light. Due to this activity, the usage of these compounds in photodynamic antibacterial studies could be considered [166].…”