Журнал "Макрогетероциклы"

Vladimir B. Sheinin,^a@ Alexandr S. Semeikin,^b Ekaterina L. Ratkova,^b and Tatyana V. Lubimova^b

^aInstitute of Solution Chemistry of Russian Academy of Sciences, Ivanovo, 153045, Russia

^bIvanovo State University of Chemistry and Technology, Ivanovo, 153000, Russia

^@Corresponding author E-mail: vbs@isc-ras.ru

Reaction of 5-(3’-oxyphenyl)-2,3,7,8,12,18-hexamethyl-13,17-diamylporphyrin with polyethylene glycol bis(ptoluenesulfonates) in the presence of cesium carbonate in boiling mixture of acetonitrile and DMFA leads to diporphyrin-O,O’-bis[3-(2,3,7,8,12,18-hexamethyl-13,17-diamylporphyrin-5-yl)phenyl]-pentaethylene glycol (I). The porphyrin-precursor was synthesized by condensation of 3,3’-diamyl-4,4’-dimethyldipyrrolylmethane-2,2’ with 2-formyl-3,4-dimethylpyrrole in the presence of hydrobromic acid in butanol, and following cyclization (without isolation) of intermediate biladiene-а,c dihydrobromide with 3-hydroxybezaldexyde. Values of lgKb1 (13.30±0.01) and lgKb2 (9.70±0.03) for protonation equilibriums of I were measured spectropotentiometrically in acetonitrile at 298 K. It was found that two interconnected porphyrin fragments are protonated independently.