Protonation Equilibriums of Porphin, 5,10,15,20-Tetraphenylporphin, 5,10,15,20-Tetrakis(4’-sulfonatophenyl)­porphin in Methanol

Abstract

Ключевые слова: Тетра(сульфонатофенил)порфин, протонирование, pH-управляемый рецептор, J-агрегаты.

The Direct Synthesis of 2-N-Methyl-5,10,15,20-tetrakis-(4′-sulfophenyl)-2-aza-21-carbaporphyrin J-Aggregates

“…The excess of sulfuric acid was neutralized with aqueous ammonia until J-aggregates dissolution, the color has changed from dark-red to green as a result of tetraanion H 2 МеIP(PhSO 3 -) 4 formation (6) (Figure 2,d). A part of tetraanions solution was evaporated in water bath until green color disappearance and J-aggregates reprecipitation (7). After the ammonium sulfate solution decantation the crude J-aggregates were isolated.…”

Features of Inverted Tetrasulfophenylporphyrin Protonation. Crucial Role of Hydrogen Bonds

“…According to second Etter's Rule, [33] IMHB that close sixmembered cycles have an advantage over intermolecular hydrogen bonds and will block intracyclic atoms from interaction with solvents and anions, as well as in porphyrins, where bifurcated IMHB protects the reaction centers of Н 2 Р and Н 3 Р + platforms from intermolecular interactions with polar solvents and anions. [34][35][36][37][38][39] The singularity of aromatic tetrapyrrole platforms is the presence of the conventional meso-plane C5C10C15C20, which is only slightly deformed even with a strong distortion of the macrocycle. As a result of intramolecular hydrogen repulsion (IMHR) internal CH-proton escapes from the meso-plane at 0.59 nm, and the inverted (1) ring unfolds at 21.53 degrees ( Table 2).…”

Supramolecular Regioselectivity of meso-Phenylporphyrin Sulfonation. Synthesis of 5,10,15-Tris(4’-sulfophenyl)porphine

“…The driving force of meso-phenylporphyrins dissolution in sulphuric acid is the formation of supramolecular complexes of doubly protonated porphyrinic platform Н 4 Р 2+ which is an anion receptor [12][13][14][15] with two hydrosulfate anions (1).…”