Solvatochromism, Acidochromism and Photochromism of the 2,6-Bis(4-hydroxybenzylidene) Cyclohexanone Derivative

Homocianu, Mihaela; Serbezeanu, Diana; Vlad‐Bubulac, Tăchiță

doi:10.3390/ijms24065286

Cited by 2 publications

(1 citation statement)

References 34 publications

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“…This property makes bis(arylidene)cycloalkanones useful in the development of photoresponsive materials and devices, such as molecular switches and optical data storage. 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.…”

Section: Introductionmentioning

confidence: 99%

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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Section: Introductionmentioning

confidence: 99%

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

Starostin,

Freidzon,

Gromov

2023

IJMS

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show abstract

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

Starostin¹,

Freidzon²,

Gromov³

2023

Preprint

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Photophysical properties of a series of bis(arylydene)cycloalkanone dyes with various donor substituentns are studied by 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 (raise of 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.

show abstract

Solvatochromism, Acidochromism and Photochromism of the 2,6-Bis(4-hydroxybenzylidene) Cyclohexanone Derivative

Cited by 2 publications

References 34 publications

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

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

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

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