NİTROVİNİL AREN BİLEŞİKLERİNE SUBSTİTÜYE DİPİROLMETAN VE TRİPİRAN BİLEŞİKLERİNİN KATILMA TEPKİMELERİ VE ÜRÜNLERİN ELEKTROKİMYASI

Abstract

Tripyrrane and bilane compounds are important building blocks in the synthesis of porphyrin and porphyrin-like macrocyclic compounds. These compounds form as by products in the synthesis of dipyrromethanes and their isolation from the reaction mixture requires very long chromatographic processes. Heteroatom-bearing dipyrromethane and tripyrrane compounds are very few in the literature. Selective synthesis of non-symmetric oxatripyrrane and thiatripyrrane compounds is important in synthetic organic chemistry, as known oxatripyrrane and thiatripyrrane compounds are generally symmetrical. In this work, addition reactions of meso-substituted dipyrromethane to nitrovinyl arenes in ether and in the presence of I2 catalyst have been carried out and non-symmetrical oxatripyrrane and thiatripyrrane compounds were obtained in moderate to high yields. In these reactions, symmetrical dioxabilane and dithiabilane compounds have formed as side products. Non-symmetrical oxabilane and thiabilane compounds were obtained as main product with moderate yields by the addition of 5,10-diphenyltripyrrane to nitrovinyl arenes in ether and in the presence of I2 catalyst. Synthesized products were characterized by 1H NMR, 13C NMR and HRMS techniques. Electropolymerization of oxatripyrrane, thiatripyrrane, dioxabilane and dithiabilane compounds were carried out and the electrochemical properties of the modified surfaces were investigated.