Self-assembly involving hydrogen bonds. Spectral properties and structure of supramolecular complexes of bis-aza-18-crown-6-containing dienones with alkanediammonium salts

Fomina, M. V.; Kurchavov, N. A.; Freidzon, Alexandra Ya.; Nuriev, V. N.; Ведерников, А. И.; Strelenko, Yuri A.; Gromov, S. P.

doi:10.1016/j.jphotochem.2020.112801

Cited by 8 publications

(7 citation statements)

References 35 publications

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“…The optimized geometries were taken from the PBE0/6-31+G(d,p)/DPCM calculation. Previously, we have shown that for dienones, solvent effects are important to properly reproduce the structures and conformation energies.…”

Section: Methodsmentioning

confidence: 99%

Structure–Property Relationships of Dibenzylidenecyclohexanones

et al. 2022

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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.

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Section: Methodsmentioning

confidence: 99%

Structure–Property Relationships of Dibenzylidenecyclohexanones

et al. 2022

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“…The optimized geometries were taken from the B3LYP/6-31 + G(d,p)/DPCM calculation. Previously [ 33 ], we have shown that, for dienones, the solvent effects are important to properly reproduce the structures and conformation energies.…”

Section: Methodsmentioning

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

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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.

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“…The formation of complex 1∙2 leads to almost complete quenching of fluorescence of 1 , which supports the hypothesized charge-transfer nature of this complex. Previously, we studied the complex formation of 1 with a number of diammonium cations NH 3 + (CH 2 ) n NH 3 + with polymethylene chain length n = 2–12 ( Fomina et al, 2020 ). A pseudocyclic complex was found to form in the case of the 1,12-dodecanediammonium ion 3 .…”

Section: Resultsmentioning

confidence: 99%

“…Compounds 1 , 2 and 1,12-dodecanediammonium diperchlorate (compound 3 ) were prepared according to known procedures (refs: Fomina et al, 2020 ; Gromov et al, 1999 ; Gromov et al, 2009 , respectively).…”

Section: Methodsmentioning

confidence: 99%

A novel fluorescent sensor for diammonium and metal ions based on a supramolecular charge-transfer complex of bis(aza-18-crown-6)-containing dienone

Gromov,

Fomina,

Zdorovenko

et al. 2023

Front. Chem.

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A bis(aza-18-crown-6)-containing 2,5-di(benzylidene)cyclopentanone and a bis(ammoniopropyl) derivative of 1,2-di(4-pyridyl)ethylene in MeCN were found to form a supramolecular charge-transfer complex, which can act as an “off–on” fluorescent sensor for the Ca2+ and 1,12-dodecanediammonium ions. The molecular structure of this complex in solution was studied by density functional theory calculations.

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Self-assembly involving hydrogen bonds. Spectral properties and structure of supramolecular complexes of bis-aza-18-crown-6-containing dienones with alkanediammonium salts

Cited by 8 publications

References 35 publications

Structure–Property Relationships of Dibenzylidenecyclohexanones

Structure–Property Relationships of Dibenzylidenecyclohexanones

Synthesis, Structure and Photochemistry of Dibenzylidenecyclobutanones

A novel fluorescent sensor for diammonium and metal ions based on a supramolecular charge-transfer complex of bis(aza-18-crown-6)-containing dienone

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