Energy transfer, fluorescence and photoisomerization of styrylquinoline–naphthol dyads with dioxypolymethylene bridges

Будыка, М. Ф.; Sadykova, K. F.; Гавришова, Т. Н.

doi:10.1016/j.jphotochem.2012.05.016

Cited by 11 publications

(7 citation statements)

References 42 publications

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“…The photophysical and photochemical properties of the dyads are studied in comparison with those of the individual model components, MeSQ and 3-methoxynapthol-2 MeNp, Scheme 12. Similar to the above-studied dyads, in the styrylquinoline-naphthol dyads, the dyad absorption spectrum does not depend on the bridge length and is a sum of the spectra of the constituting SQ and Np fragments, Table 2 [58]. As a representative of the series, the absorption spectrum of the dyad SQ3Np is depicted in Fig.…”

Section: Photonics Of Styrylquinoline-naphthol Dyadsstyrylquinoline mentioning

confidence: 54%

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Photonics of styrylquinoline dyads

Будыка¹

2015

Organic Photonics and Photovoltaics

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Three types of bichromophoric styrylquinoline (SQ) dyads are discussed in the review: bisstyrylquinoline dyads, styrylquinoline-merocyanine dyads, and styrylquinoline-naphthol dyads, in comparison with the corresponding model monochromophoric compounds. A variety of photochemical and photophysical processes is observed in the dyads: photoluminescence, reversible and kinetic-driven one-way photoisomerization, [2+2]photocycloaddition with formation of a single rctt-isomer of the cyclobutane derivative, Forster resonance energy transfer (FRET) where the SQ chromophore can act as an energy donor or acceptor. Operation of the dyads as photoswitches and molecular logic gates is also considered.

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Section: Photonics Of Styrylquinoline-naphthol Dyadsstyrylquinoline mentioning

confidence: 54%

“…In styrylquinoline-naphthol dyads SQnNp (n = 2 -5), the SQ fragment is linked by dioxypolymethylene bridge -O-(CH 2 )n-O-with fragment of 2-naphthole (Np) [54][55][56][57][58]. Two fragments in the dyads SQnNp possess opposite acidbase properties.…”

Section: Photonics Of Styrylquinoline-naphthol Dyadsstyrylquinoline mentioning

confidence: 99%

Photonics of styrylquinoline dyads

Будыка¹

2015

Organic Photonics and Photovoltaics

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“…However, the dissociation of the naphthol hydroxy group in the excited state was strongly hindered because of strong intramolecular hydrogen bonding between the hydroxy and alkoxy groups and mesomeric effect of the alkoxy group in the 3-position of the naphthalene ring. In particular, the pK a * value increased to 6.6 against pK a * 2.8 for unsubstituted 2-naphthol [12].…”

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“…6-Hydroxynaphthalene-2-carboxylic acid derivatives are precursors of liquid crystals [9,10]. Bifunctional compounds comprising two non-conjugated 2-styrylquinoline and 2-naphthol chromophore subsystems attract interest as model substrates for studying various photophysical and photochemical processes, including energy transfer [11,12] and photoinduced proton transfer. It is known that styrylquinoline is a photobase and that naphthol is a photoacid: excitation to the singlet state (S 1 ) enhances the basicity of styrylquinoline [13] and acidity of naphthol [14].…”

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Synthesis and acid-base properties of bifunctional compounds based on 2-styrylquinoline and 6-hydroxynaphthalene-2-carboxylic acid

et al. 2015

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The reaction of 6-hydroxynaphthalene-2-carboxylic acid with 2-{(E)-2-[4-(ω-bromoalkoxy)phenyl]-ethenyl}quinolines gave ω-{4-[(E)-2-(quinolin-2-yl)ethenyl]phenoxy}alkyl 6-hydroxynaphthalene-2-carboxylates possessing both photoacid and photobase properties. The acidities of the naphthol fragment in the ground (pK a ) and singlet excited states (pK a *) of 3-{4-[(E)-2-(quinolin-2-yl)ethenyl]phenoxy}propyl 6-hydroxynaphthalene-2-carboxylate are pK a 9.0 and pK a * 2.4, and of the quinoline fragment, pK a 4.6, pK a * 12.6, respectively.

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Spectral and luminescent properties and photoisomerization of substituted styrylbenzoquinolines

Будыка

Гавришова

et al. 2015

High Energy Chem

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Derivatives of 2 styrylquinoline (2SQ), due to their photochemical activity, are used to simulate the action of photonic molecular switches and logic gates [1][2][3][4][5]. Photoisomerization quantum yields of these com pounds can reach values of 0.5 and above, but their disadvantage is relatively small fluorescence quantum yields (ϕ fl ), not exceeding a few hundredths [6]. To address this shortcoming, it is necessary to pass to het erodiarylethylenes, which possess pronounced fluo rescent properties (ϕ fl > 0.1), but it is important that the photoactivity of the compounds, that is, ability to photoisomerization, should persist. For example, when passing from 2SQ to the bis quinoline derivative of distyrylbenzene the ϕ fl value increases significantly (up to 0.63), but the quantum yield of the trans-cis photoisomerization reaction of the first double bond EE → ZE decreases steeply (down to 0.03), and the trans-cis photoi somerization reaction of the second double bond ZE → ZZ does not occur [7].It is known that the angular annulation of the quin oline nucleus, that is, passing from 2SQ to 3 styryl benzo[f]quinoline (3SBQ), leads to a significant increase in the fluorescence quantum yield up to 0.74, with the quantum yield of trans-cis photoisomeriza tion retaining a fairly high value (ϕ tc = 0.19), and the quantum yield of the reverse reaction of cis-trans pho toisomerization ϕ ct = 0.38 [8].Note that photoswitchable fluorophores are "real chemical basis" of one of the methods of ultrahigh res olution fluorescent microscopy ("nanoscopy") [9-11], for the development of which the Nobel Prize in Chemistry was awarded in 2014.To find out photochromes of the class of heterodi arylethylenes, being also fluorophores, that is, satisfy ing the conditions ϕ tc > 0.1 and ϕ fl > 0.1, we studied in this work a number of 3SBQ derivatives: trans 3 (3 methoxystyryl)benzo[f]quinoline (3MSBQ), trans 3 (4 methoxystyryl)benzo[f]quinoline (4MSBQ), and trans 3 (4 methoxycarbonylstyryl)benzo[f]quinoline (4MCSBQ) (Scheme 1): N N PHOTOCHEMISTRY Abstract-The spectral, luminescent, and photochemical properties of 3 styrylbenzo[f]quinoline (3SBQ)derivatives containing methoxy and methoxycarbonyl groups have been studied. All of these compounds luminesce in the region of 380-480 nm with quantum yields up to 0.74 and undergo reversible photoisomer ization with quantum yields of 0.2-0.5. It has been found that compounds with a methoxy group at the meta position and a methoxycarbonyl group at the para position of the styryl moiety are unstable photochromes and also undergo other photochemical reactions side relative to photoisomerization. The absorption spectra of the two 3SBQ s conformers calculated by the density functional theory (DFT) method (TD B3LYP/6 31G*) describe well the experimental spectrum. The analysis of the structures of molecular orbitals and tran sitions between them has made it possible to explain the observed effects of substituents on the absorption spectrum of 3SBQ.

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Energy transfer, fluorescence and photoisomerization of styrylquinoline–naphthol dyads with dioxypolymethylene bridges

Cited by 11 publications

References 42 publications

Photonics of styrylquinoline dyads

Photonics of styrylquinoline dyads

Synthesis and acid-base properties of bifunctional compounds based on 2-styrylquinoline and 6-hydroxynaphthalene-2-carboxylic acid

Spectral and luminescent properties and photoisomerization of substituted styrylbenzoquinolines

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