Synthesis of sulfanyl porphyrazines with bulky peripheral substituents – Evaluation of their photochemical properties and biological activity

Sulfanyl Porphyrazines with Morpholinylethyl Periphery—Synthesis, Electrochemistry, and Photocatalytic Studies after Deposition on Titanium(IV) Oxide P25 Nanoparticles

“…The only difference between the UV–Vis spectra of 4 and 5 was noted in the region between 450 and 550 nm, where, for Pz 4, only a weak absorption maximum at 497 nm appeared. A similar effect was noted before for sulfanyl porphyrazines with peripheral phthalimide motifs [ 38 ].…”

“…Symmetrical octa-substituted sulfanyl porphyrazines, unlike their unsymmetrical derivatives, usually present low singlet oxygen generation quantum yields, and therefore their biological activities are limited [ 32 , 33 ]. Recently, many symmetrical and unsymmetrical magnesium(II) and zinc(II) sulfanyl porphyrazines with bulky dendrimeric periphery were synthesized and evaluated in terms of their suitability for photodynamic therapy (PDT) [ 34 , 35 , 36 , 37 , 38 ]. In addition, some sulfanyl porphyrazines and phthalocyanines with morpholinyl moieties were studied as photosensitizers for PDT and photodynamic antimicrobial chemotherapy (PACT) and revealed promising potential [ 39 , 40 , 41 ].…”

A Synergistic Effect of Phthalimide-Substituted Sulfanyl Porphyrazines and Carbon Nanotubes to Improve the Electrocatalytic Detection of Hydrogen Peroxide

“…A magnesium(II) porphyrazine containing phthalimide substituents ( 1 ) and its free-base analog ( 2 ) were synthesized using a three-step published procedure [ 39 ]. Pz 2 was metallated in DMF with iron(II) bromide and cobalt(II) chloride hexahydrate to give iron(II) sulfanyl porphyrazine 3 and cobalt(II) sulfanyl porphyrazine 4 , respectively ( Scheme 1 ).…”

“…Cobalt(II) porphyrazine 4 showed a more intense, sharp Q-band with a maxima at 643–646 nm and log ε values of 4.59–4.94 ( Table S2 in the Supplementary Information ). It is worth noting that the introduction of the cobalt(II) cation in the porphyrazine core produced a significant Q-band hypsochromic shift of about 25–30 nm compared with the previously elaborated magnesium(II) and zinc(II) analogues [ 39 ].…”

“…2,3,7,8,12,13,17,18-Octakis[( N -ethylphthalimide)thio]porphyrazinato magnesium(II) ( Pz1 ) and 2,3,7,8,12,13,17,18-octakis[( N -ethylphthalimide)thio]porphyrazine ( Pz2 ) were synthesized using a previously published procedure [ 39 ].…”