Hydrogen-Bonded Self-assembly of Supramolecular Donor–Acceptor Complexes of (E)-Bis(18-crown-6)azobenzene with Bis(ammoniopropyl) Derivatives of Bipyridine and Dipyridylethylene in Acetonitrile

Volchkov, Valery V.; Khimich, M. N.; Melnikov, Mikhail Ya.; Egorov, Anton E.; Starostin, Roman O.; Freidzon, Alexandra Ya.; Dmitrieva, S. N.; Громов, С. П.

doi:10.1007/s10953-023-01271-6

Cited by 4 publications

(2 citation statements)

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“…Bis(arylidene)cycloalkanone compounds display solvatochromic properties [4][5][6] and can be applied, for example, for determining the polarity of a medium [7][8][9] or as pH sensors [10]. Bis(arylidene)cycloalkanones modified with ionophoric fragments [11][12][13] form a basis for photocontrolled supramolecular devices. Nanoparticles are used to modify the spectra of ketocyanine dyes [14].…”

Section: Introductionmentioning

confidence: 99%

“…The electrochemistry and positions of the a Bis(arylidene)cycloalkanone compounds were found to exhibit strong two-photon absorption properties, which could be useful for two-photon microscopy [15] and photodynamic therapy [16][17][18]. The studies found that the photophysical properties of the compounds were dependent on the size of the alicyclic ring, with larger rings leading to lower fluorescence quantum yields and shorter excited-state lifetimes [13]. Ref.…”

Section: Introductionmentioning

confidence: 99%

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Theoretical Study of Structure and Photophysics of Homologous Series of Bis(arylydene)cycloalkanones

Starostin,

Freidzon,

Gromov

2023

IJMS

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Photophysical properties of a series of bis(arylydene)cycloalkanone dyes with various donor substituents are studied using quantum chemistry. Their capacity for luminescence and nonradiative relaxation through trans–cis isomerization is related to their structure, in particular, to the donor capacity of the substituents and the degree of conjugation due to the central cycloalkanone moiety. It is shown that cyclohexanone central moiety introduces distortions and disrupts the conjugation, thus leading to a nonmonotonic change in their properties. The increasing donor capacity of the substituents causes increase in the HOMO energy (rise in the oxidation potential) and decrease in the HOMO–LUMO gap, which results in the red shift of the absorption spectra. The ability of the excited dye to relax through fluorescence or through trans–cis isomerization is governed by the height of the barrier between the Franck–Condon and S1–S0 conical intersection regions on the potential energy surface of the lowest π-π* excited state. This barrier also correlates with the donor capacity of the substituents and the degree of conjugation between the central and donor moieties. The calculated fluorescence and trans–cis isomerization rates are in good agreement with the observed fluorescence quantum yields.

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