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ISSN 1998-9539

Synthesis and Investigation of Basicity of Diporphyrin with Polyethylenoxide Spacer

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


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:


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.

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