Photo- and PH-switchable fluorescent diarylethenes based on 2,3-diarylcyclopent-2-en-1-ones with dialkylamino groups

Ширинян, Валерий З.; Lonshakov, Dmitry V.; Lvov, Andrey G.; Kavun, Alexey M.; Yadykov, Anton V.; Krayushkin, M. M.

doi:10.1016/j.dyepig.2015.09.027

Cited by 15 publications

(6 citation statements)

References 48 publications

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“…The literature data 14 and our own studies 8,12,13,15 indicate the promise of this phototransformation. The reaction can be used to synthesize a wide variety of polyaromatic (heteroaromatic) compounds with different functional groups.…”

Section: ■ Introductionmentioning

confidence: 61%

Photochemical Rearrangement of Diarylethenes: Reaction Efficiency and Substituent Effects

et al. 2017

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In recent years, great synthetic potential of the photorearrangement of diarylethenes leading to naphthalene derivatives via a cascade process of photocyclization/[1,n]-H shift/cycloreversion has been demonstrated. In this work, first a multifaceted study of the influence of various factors on the efficiency of the photorearrangement of diarylethenes of furanone series containing benzene and oxazole derivatives as aryl residues has been carried out. The efficiency of this phototransformation (quantum yields) and the effect of methoxy substituents in the phenyl moiety have been studied. Despite the multistage process, the quantum yields of the photorearrangement are rather high (0.34-0.49). It has been found that the efficiency of photocyclization of diarylethenes increases with the introduction of electron-donating methoxy groups in the phenyl moiety. Using the DFT calculations, we have been able to estimate in the photoinduced isomer the distance between hydrogen atom and carbon atom to which it migrates in the result of the sigmatropic shift. For all studied diarylethenes, this value was 2.67-2.73 Å, which is less than the sum of van der Waals radii of carbon and hydrogen atoms (2.9 Å).

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Section: ■ Introductionmentioning

confidence: 61%

Photochemical Rearrangement of Diarylethenes: Reaction Efficiency and Substituent Effects

et al. 2017

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“…Previously, the titled compound was considered as E-isomer (E-D1-o in Scheme 1). 15 Electronic absorption spectra of solutions were recorded using the spectrophotometers Agilent 8453 (Agilent Technologies, USA) and Cary 50 (Varian, USA). Light sources for stationary photolysis experiments were light-emitting diodes (Edinburgh Instruments, UK) and a high-pressure mercury lamp with a set of glass filters for selecting the desired spectral region.…”

Section: Methodsmentioning

confidence: 99%

“…These molecules feature strong fluorescence in the initial state, while UV or blue light irradiation causes reversible reduction of the emission intensity. 15 The ICT (intramolecular charge transfer) excited state was shown to be responsible for the luminescence properties, which determines the strong dependence of emission vs. solvent polarity. 16 The most exciting property is a complex photoswitching, comprising the predominant E -/ Z -isomerization of the arylidene core in polar solvents and 6π-electrocyclization in non-polar media.…”

Section: Introductionmentioning

confidence: 99%

Multifunctional fluorescent diarylethene: time-resolved study of photochemistry

Semionova

Pozdnyakov

Grivin

et al. 2023

Phys. Chem. Chem. Phys.

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“…Diarylethene V and its analogues, with the ability for easy chemical modification of the cyclopentenone bridge, have been proposed by our group . This feature allows control of the spectral properties and thermal stability, the efficiency of photocyclization, and also ability to obtain photochromes with modulated fluorescence . The ethene bridge modification approach was also used in several other works …”

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confidence: 90%

Aerobic Dimerization of Ethyl 4-Thienyl-3-ketobutanoate toward a Modifiable Photochromic Diarylethene Precursor

Lvov

Milevsky²,

Yanina

et al. 2017

Org. Lett.

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A unique chemical transformation, the base-induced aerobic dimerization of ethyl 4-(2,5-dimethylthiophen-3-yl)-3-ketobutanoate leading to photochromic diarylethene with a 4-hydroxy-4-methylcyclopent-2-ene-1-one as an ethene bridge, is described. This compound is easily subjected to various chemical modifications and can be used as a new diarylethene precursor to produce photoactive compounds with desired properties and functions.

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Photo- and PH-switchable fluorescent diarylethenes based on 2,3-diarylcyclopent-2-en-1-ones with dialkylamino groups

Cited by 15 publications

References 48 publications

Photochemical Rearrangement of Diarylethenes: Reaction Efficiency and Substituent Effects

Photochemical Rearrangement of Diarylethenes: Reaction Efficiency and Substituent Effects

Multifunctional fluorescent diarylethene: time-resolved study of photochemistry

Aerobic Dimerization of Ethyl 4-Thienyl-3-ketobutanoate toward a Modifiable Photochromic Diarylethene Precursor

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