15,porphine was obtained by three-stage synthesis from tetraphenylporphyrin under conditions of supramolecular control of regioselectivity of nitration and sulfonation reactions. In acidic medium (pH ≈ 2) the trianion H 2 P(PhNH 2 )(PhSO 3 -) 3 is protonated at the porphyrin platform and the amino group to form the aqua complex of the zwitterion [H 4 P 2+ (PhNH 3 )(PhSO 3 H)(PhSO 3 -) 2 ](H 2 O) 2 , which is self-assembled into porphyrin nanotubes (PNTs), the outer surface of which is covered with positively charged groups -PhNH 3 + , and the inner surface with electroneutral groups -PhSO 3 H. By the action of nitrous acid, stable diazotized PNTs were obtained. Supramolecular self-assembly inhibits the azo coupling reaction of H 4 P 2+ (PhN 2 + )(PhSO 3 H) (PhSO 3 -) 2 tectons with H-acid in an acidic medium. H-Conjugate was obtained by azo coupling in an alkaline medium (pH ≈ 10), where diazotized PNTs are destroyed with formation of the diazocompound H 2 P(PhN 2
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