Optical and electrochemical properties of novel fused tricyclic thiophene-15-crown-5 systems and their complexes with Mg and Ba ions

New polycyclic aromatic derivatives annulated both with thiophene and with 15-crown-5 ether moieties, crown naphthothiophenes, were synthesized via the Mallory photocyclization with the use of iodine as the mild oxidizer, while two isomeric products were readily separated by column chromatography. Their complexation with Ba2+ and Mg2+ cations was examined by both optical and electrochemical methods. Spectroelectrochemical studies indicate that the obtained compounds, depending on their structure, can be chemically stable in the oxidized state.

Automated summary

New polycyclic aromatic derivatives, crown naphthothiophenes, annulated both with thiophene and with 15-crown-5 ether moieties, were successfully synthesized via the Mallory photocyclization. Their complexation with Ba2+ and Mg2+ cations was investigated using optical and electrochemical methods, revealing the chemical stability of the compounds in the oxidized state depending on their structure.