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

Molecules. 2020 Jul 6;25(13):3082. doi: 10.3390/molecules25133082.

Abstract

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.

Keywords: ((arylamino)methylene)indolin-2-ones; ON/OFF switches; anions of isatin arylhydrazones; hydrazo-azo tautomerization; kinetics; photoisomerization.

MeSH terms

  • Anions / chemistry*
  • Chromatography, High Pressure Liquid
  • Hydrazones / chemical synthesis
  • Hydrazones / chemistry*
  • Indoles / chemistry*
  • Isatin / chemistry*
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Photochemistry
  • Spectrophotometry, Ultraviolet
  • Stereoisomerism

Substances

  • Anions
  • Hydrazones
  • Indoles
  • indolin-2-one
  • Isatin