Novel Linear Bis-Crown Receptors with Cross-Conjugated and Conjugated Central Cores

Вацадзе, С. З.; Gromov, S. P.

doi:10.6060/mhc171142v

Cited by 14 publications

(7 citation statements)

References 65 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In the case of dienones, it is especially important to explore their conformational behavior in solutions, which is important for prediction and determination of the structures of supramolecular systems based on bis-crown-containing dienones. 24 Therefore, we studied the structural characteristics of ( E , E )-dienones 1d and 2 using various NMR techniques.…”

Section: Results and Discussionmentioning

confidence: 99%

“…It is not always possible to compare NMR data, characterizing the structure of molecules in solution with crystallographic data for the whole series, since the crystals of high quality are not available for all compounds. In the case of dienones, it is especially important to explore their conformational behavior in solutions, which is important for prediction and determination of the structures of supramolecular systems based on bis-crown-containing dienones . Therefore, we studied the structural characteristics of ( E , E )-dienones 1d and 2 using various NMR techniques.…”

Section: Results and Discussionmentioning

confidence: 99%

“…23 Within the framework of the project on the design of photoswitchable supramolecular systems, we started a comprehensive targeted investigation of cross-conjugated dienones containing ionophoric substituents such as crown ethers. 24 The idea of this study was to generate hybrid molecules combining two functional components: an ionophoric group capable of coordination to metal ions, ammonium ions, or other analytes and a photoswitchable group providing control of the coordination by exposure to external light. For a more in-depth understanding of the photochemical reactions that take place, it is necessary to study in detail the properties and physicochemical characteristics of model compounds.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Structure–Property Relationships of Dibenzylidenecyclohexanones

et al. 2022

Self Cite

View full text Add to dashboard Cite

A series of symmetrical dibenzylidene derivatives of cyclohexanone were synthesized with the goal of studying the physicochemical properties of cross-conjugated dienones (ketocyanine dyes). The structures of the products were established and studied by X-ray diffraction, NMR spectroscopy, and electronic spectroscopy. All products had the E , E -geometry. The oxidation and reduction potentials of the dienones were determined by cyclic voltammetry. The potentials were shown to depend on the nature, position, and number of substituents in the benzene rings. A linear correlation was found between the difference of the electrochemical oxidation and reduction potentials and the energy of the long-wavelength absorption maximum. This correlation can be employed to analyze the properties of other compounds of this type. The frontier orbital energies and the vertical absorption and emission transitions were calculated using quantum chemistry. The results are in good agreement with experimental redox potentials and spectroscopic data.

show abstract

Section: Results and Discussionmentioning

confidence: 99%

Section: Results and Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Structure–Property Relationships of Dibenzylidenecyclohexanones

et al. 2022

Self Cite

View full text Add to dashboard Cite

show abstract

“…The NMR data are rarely compared with the structures of compounds known from a crystallographic analysis because it is impossible to obtain high-quality crystals for the whole series. In the case of dienones, the determination of their conformational behavior in solutions is especially important for the prediction and determination of the structures of supramolecular systems based on bis-crown-containing dienones [ 32 ]. Therefore, we studied the structural characteristics of ( E , E )-dienones 1c and 2 using various NMR techniques.…”

Section: Resultsmentioning

confidence: 99%

“…With the purpose of developing photoswitchable supramolecular systems, we started a comprehensive study of cross-conjugated dienones containing crown-ether moieties as ionophore substituents [ 32 , 33 ]. This research is meant to design hybrid molecules combining two functional moieties: an ionophore able to bind metal and ammonium cations and guest molecules, and a photoswitchable moiety needed for controlled binding, using light as an energy source.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Structure and Photochemistry of Dibenzylidenecyclobutanones

et al. 2022

Self Cite

View full text Add to dashboard Cite

A series of symmetrical dibenzylidene derivatives of cyclobutanone were synthesized with the goal of studying the physicochemical properties of cross-conjugated dienones (ketocyanine dyes). The structures of the products were established and studied by X-ray diffraction and by NMR and electronic spectroscopy. All the products had E,E-geometry. The oxidation and reduction potentials of the dienones were determined by cyclic voltammetry. The potentials were shown to depend on the nature, position, and number of substituents in the benzene rings. A linear correlation was found between the difference of the electrochemical oxidation and reduction potentials and the energy of the long-wavelength absorption maximum. This correlation can be employed to analyze the properties of other compounds of this type. Quantum chemistry was used to explain the observed regularities in the electrochemistry, absorption, and fluorescence of the dyes. The results are in good agreement with the experimental redox potentials and spectroscopy data.

show abstract