Isatin-1,8-Naphthalimide Hydrazones: A Study of Their Sensor and ON/OFF Functionality

Tisovský, Pavol; Horváth, Miroslav; Csicsai, Klaudia; Donovalová, Jana; Filo, Juraj; Cigáň, Marek; Sokolík, Róbert; Addová, Gabriela; Gáplovský, Anton

doi:10.3390/molecules24030397

Cited by 8 publications

(5 citation statements)

References 27 publications

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“…At the same time, the intensity of absorption around 400 nm decreases. The same changes with the change in concentration were observed in the case of isatin naphthylimide hydrazones [ 11 ] and isatin 4-nitrophenyl-hydrazone [ 12 ].…”

Section: Resultssupporting

confidence: 61%

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

et al. 2020

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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.

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Section: Resultssupporting

confidence: 61%

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

et al. 2020

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“…The same change in UV-Vis spectra of the Z -isomers was also observed at 80 °C in DMF (Figure 2a). Such behavior during photolysis was also observed in the case of other isatin arylhydrazones with strongly deactivated aryl [13,17].…”

Section: Resultsmentioning

confidence: 58%

ON/OFF Photostimulation of Isatin Bipyridyl Hydrazones: Photochemical and Spectral Study

et al. 2019

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Four novel isatin hydrazones containing bipyridyl fragments were synthesized as potential ON/OFF switches. Hydrazone Z-isomers exhibit high thermal stability. The characteristic photochemical reaction for all studied hydrazones is the Z–E isomerization in CHCl3. After irradiation of hydrazones 1 and 2 in dimethylformamide (DMF), the photoreaction products are tautomers. When using light with the appropriate wavelength, the photo-tautomerization reaction is reversible. In these conditions, studied hydrazones have ON/OFF switch properties. In the case of hydrazones 1 and 2, by alternating heat and light stimulation it is possible to control the isomerization process reversibly. In the presence of fluoride ions, NH hydrogen from the studied hydrazones is cleaved, and the corresponding anions are formed. The resulting anions of Z-isomers are changed to the corresponding E-isomer at room temperature.

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“…The process of hydrazo‐azo tautomerization depends on their structure and affects the course of geometric isomerization. Tautomerization of hydrazones in their nonanionic form can be observed only for E ‐isomers [10] . The Z ‐isomers do not tautomerize under these conditions.…”

Section: Methodsmentioning

confidence: 90%

“…Tautomerization of hydrazones in their nonanionic form can be observed only for E-isomers. [10] The Zisomers do not tautomerize under these conditions. Isatin arylhydrazones and anil-like compounds are found in a more stable Z hydrazo form.…”

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confidence: 96%

A New Strategy for the Preparation of E Isomers of Hydrazones and Anil‐Like Compounds: Thermally Stimulated Isomerization of Z Isomers of Anions

et al. 2021

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A new, simple method for the preparation of E‐isomers of hydrazones and anil‐like compounds from Z‐isomers of these compounds has been developed. In DMF, the Z‐isomers of these compounds in the presence of tetrabutylammonium fluoride (TBAF) or tetrabutylammonium acetate (TBAA) gave the corresponding N anions of the Z‐isomers, which are isomerized to the N anions of the E‐isomers even at room temperature. Upon addition of a protic solvent (H2O, or CH3OH) to this reaction mixture, the N anion of the E‐isomer was immediately quantitatively converted to the E‐isomer of the corresponding nonionic compound, which can be readily isolated by methods commonly used in the synthesis.

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Isatin-1,8-Naphthalimide Hydrazones: A Study of Their Sensor and ON/OFF Functionality

Cited by 8 publications

References 27 publications

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

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

ON/OFF Photostimulation of Isatin Bipyridyl Hydrazones: Photochemical and Spectral Study

A New Strategy for the Preparation of E Isomers of Hydrazones and Anil‐Like Compounds: Thermally Stimulated Isomerization of Z Isomers of Anions

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