Effect of a =X-NH-Fragment, (X = C, N), on Z/E Isomerization and ON/OFF Functionality of Isatin Arylhydrazones, ((Arylamino)Methylene)Indolin-2-Ones and Their Anions

• Published in: Molecules (Basel, Switzerland) Vol. 25; no. 13; p. 3082
• Main Authors: Tisovský, Pavol, Csicsai, Klaudia, Donovalová, Jana, Šandrik, Róbert, Sokolík, Róbert, Gáplovský, Anton
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 06.07.2020; MDPI
• Subjects: ((arylamino)methylene)indolin-2-ones; Anions - chemistry; anions of isatin arylhydrazones; Chromatography, High Pressure Liquid; Equilibrium; hydrazo-azo tautomerization; Hydrazones - chemical synthesis; Hydrazones - chemistry; Indoles - chemistry; Isatin - chemistry; kinetics; Magnetic Resonance Spectroscopy; Molecular Structure; ON/OFF switches; Photochemistry; photoisomerization; Solvents; Spectrophotometry, Ultraviolet; Stereoisomerism; photoisomerization; hydrazo-azo tautomerization; ((arylamino)methylene)indolin-2-ones; ON/OFF switches; kinetics; anions of isatin arylhydrazones
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules25133082

The subject of this work was the study of thermally and photochemically stimulated Z ↔ E isomerization and hydrazo ↔ azo tautomerism of Z- and E-isomers of isatin arylhydrazones and ((arylamino)methylene)indolin-2-ones and their anions. Using NMR, UV-Vis spectroscopy, kinetic measurements, and HPLC, we studied the relationship of structure, (Z- and E-isomers), of these compounds and hydrazo=azo tautomerism. The ON/OFF functionality of these compounds and their anions using light to stimulate switching between ON and OFF states was investigated. We pointed out the characterization of the effect of =N- and =CH- structural fragments and aryl structure on ON and OFF states of isatin arylhydrazones and ((arylamino)methylene)indolin-2-ones.