Tetrapyrazinoporphyrazines with different number of peripheral pyridyl rings: Synthesis, photophysical and photochemical properties

Zinc azaphthalocyanines with thiophen-2-yl, 5-methylthiophen-2-yl and pyridin-3-yl peripheral substituents: Additive substituent contributions to singlet oxygen production

“…These results, and other studies [12,13] strongly indicate that substituent effects, such as Q-band positions and singlet oxygen quantum yields, may be additive functions of the peripheral substituents on AzaPc. Therefore, in this work, we have investigated ZnAzaPc with thiophen-2-yl, 5-methylthiophen-2-yl and pyridin-3-yl substituents and tried to reveal the relationships that may influence the photophysical properties of AzaPcs.…”

“…This gives a calculated value F D ¼ 0.563 for 10 in good agreement with observed F D ¼ 0.585 for this compound. These and previous results [10,12,27] indicate that any peripheral substituent on ZnAzaPc will make a specific contribution to the singlet oxygen production of the complex, and such contributions are additive. However, other factors, e.g.…”

Dicyanomethylene Substituted Benzothiazole Squaraines: The Efficiency of Photodynamic Therapy In Vitro and In Vivo

“…The singlet oxygen ( 1 O 2 ) generation from the squaraines upon irradiation was studied using 1,3-diphenylisobenzofuran (DPBF) as the 1 O 2 indicator( Yuan et al, 2015 , Zimcik et al, 2009 ). DPBF reacts irreversibly with 1 O 2 which causes a decrease in the intensity of the DPBF absorption band at 418 nm.…”

Tetrapyrazinoporphyrazines and their metal derivatives. Part I: Synthesis and basic structural information

“…Further, their properties (e.g., lipophilicity) needs to differ somehow to enable separation of congeners by column chromatography. Separation of the mixture is performed either in the form of metal complexes [52,178,232,234,243] if the differences in the R f values between congeners are sufficiently big or in the form of metal free TPyzPzs [132,162,164,167]. Metal complexes are usually strongly tailing on silica, but this is not the case of metal free TPyzPz that, on the other hand, may suffer from lower solubility [166].…”

“…Closer investigation lead to the conclusion that the susceptible species in the reaction is the precursor, pyrazine-2,3-dicarbonitrile, and not the final macrocycle [229]. To avoid this side reaction, a number of TPyzPzs bearing alkylsulfanyl substituents were prepared using the template method with zinc acetate in DMF (yields 7-44%) [138, 155, Page 21 of 66 A c c e p t e d M a n u s c r i p 156,178,232] or with Zn(quinoline) 2 Cl 2 as the cyclotetramerization agent (48% yield of [TPyz117bPzZn]) [176]. From a number of different alkylsulfanyl substituents, the bulky tBuS groups seem to be the most promising for deep investigation, since they largely reduce the aggregation not only in organic solvents [144] but even when the octa(tert-butylsulfanyl) derivative [TPyz73PzZn] was incorporated into lipid bilayer of unilamellar liposomes [233].…”