Publications Repository - Gdańsk University of Technology

The preparation and characterization of products of the chemical and photochemical rearrangements of a 19-membered o,o'-azoxybenzocrown were presented. In photochemical rearrangement, besides expected product i.e. 19-membered o-hydroxy-o,o'-azobenzocrown (19-o-OH), obtained under defined conditions with 75% yield, also other macrocyclic products were isolated and identified, namely: 19-membered p-hydroxy-o,o'-azobenzocrown (19-p-OH), 21-membered o'-hydroxy-o,p'-azobenzocrown (21-o'-OH) and 19-membered macrocycle containing 5-membered ring bearing an aldehyde group (19-al). The structures of two atypical products of the photochemical rearrangement - 21-o'-OH and 19-al - were determined in the solid state by the X-ray method and in solution using NMR spectroscopy. Tautomeric equilibrium of the formed hydroxyazobenzocrowns and its change depending on acidity/basicity of the environment and alkali and alkaline earth metal cations complexation were studied using UV-Vis spectrophotometry, spectrofluorimetry and 1H NMR spectroscopy.

Authors

• dr hab. inż. Ewa Wagner-Wysiecka link open in new tab ,
• Paulina Szulc link open in new tab ,
• prof. dr hab. inż. Elżbieta Luboch link open in new tab ,
• prof. dr hab. inż. Jarosław Chojnacki link open in new tab ,
• dr inż. Katarzyna Szwarc-Karabyka link open in new tab ,
• dr inż. Natalia Łukasik link open in new tab ,
• Miłosz Murawski link open in new tab ,
• Michał Kosno link open in new tab