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Abstract
New products of photo- and thermal rearrangements of 19-membered azoxybenzocrown with phenyl substituents in benzene rings in the para positions to oligooxyethylene fragments are characterized. The yields of photochemical transformations depend on the solvent. Para-hydroxyazocrown is formed with yields over 50% in propan-2-ol. Ortho-hydroxyazobenzocrown is obtained with yields up to 70% in toluene/acetic acid mixture. Macrocyclic Ph-20-ester is obtained in yield 90% under thermochemical rearrangement conditions. Structure of new hydroxyazobenzocrowns and also atypical product of rearrangements, 20-membered ester, was confirmed by X-ray diffraction analysis. Azophenol⇄quinone–hydrazone tautomeric equilibrium of new hydroxyazobenzocrowns and the influence of metal cations on tautomeric equilibrium was investigated using 1H NMR and UV-Vis spectroscopy in acetonitrile. The highest value of stability constant (logK 7.25) was obtained for strontium complex of p-hydroxyazobenzocrown. For the first time p-hydroxyazobenzocrown was used as a chromoionophore in the receptor layer of an optical sensor. Comparative analysis with data obtained previously for series 19-membered analogs have shown the influence of the presence of substituents in benzene rings for the course and products distribution of photo- and thermal rearrangement. The effect of substituents was also discussed against the tautomeric equilibrium and metal cation complexation properties.
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- Category:
- Articles
- Type:
- artykuły w czasopismach
- Published in:
-
ChemPlusChem
no. 88,
pages 1 - 18,
ISSN: 2192-6506 - Language:
- English
- Publication year:
- 2023
- Bibliographic description:
- Wagner-Wysiecka E., Szulc P., Luboch E., Chojnacki J., Laskowska D., Miklaszewska P., Sowiński P.: Do Phenyl Substituents Affect the Properties of Azobenzocrown Derivatives?// ChemPlusChem -Vol. 88,iss. 6 (2023),
- DOI:
- Digital Object Identifier (open in new tab) 10.1002/cplu.202300175
- Sources of funding:
-
- COST_FREE
- Verified by:
- Gdańsk University of Technology
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