A photophysical and theoretical study of styrylanthracenes

Bartocci, G.; Masetti, F.; Mazzucato, U.; Spalletti, Anna; Orlandi, Giorgio; Poggi, Gabriella

doi:10.1039/f29888400385

Cited by 49 publications

(34 citation statements)

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“…In this study, known compounds 9-[(E)-2-phenylethenyl]anthracene PEA 1, and 9-[(E)-2-(2-naphthalenyl)ethenyl]anthracene NEA 2, (Scheme 1), were used for singlet oxygen 1 O 2 ( 1 Δg) trapping and their biological photodynamic effect on cellular cultures of L. tarentolae promastigotes was also examined. The photophysical properties of the compounds have been previously determined (24)(25)(26). The emission band near 500 nm has been assigned to fluorescence, and quantum yields have been determined to be about 0.5 for PEA 1 and about 0.6 for NEA 2 in acetonitrile.…”

Section: Resultsmentioning

confidence: 99%

9-[(E)-2-phenylethenyl]anthracene and 9-[(E)-2-(naphthalen-2-yl)ethenyl]anthracene as traps for singlet oxygen: photosensitized oxidation and photodynamic effect on Leishmania tarentolae parasites

et al. 2016

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Section: Resultsmentioning

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9-[(E)-2-phenylethenyl]anthracene and 9-[(E)-2-(naphthalen-2-yl)ethenyl]anthracene as traps for singlet oxygen: photosensitized oxidation and photodynamic effect on Leishmania tarentolae parasites

et al. 2016

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“…It was taken into consideration that these aza DAE can exist as s trans and s cis conformers (rotamers) (Scheme 3). It is known that the energy difference between the two conformers is small for 2SA, with the s trans con former (denoted as rotamer B) being somewhat more stable than the s cis conformer (denoted as rotamer A) and having a short wavelength and more intense absorption spectrum in comparison with the latter [4]. We experimentally observed the luminescence (lumi nescence excitation) spectra of aza DAE to depend upon the excitation (detection) wavelength, a fact that indicates the presence of conformers; however, the phenomenon of conformational isomerization was not investigated in detail.…”

Section: Quantum Chemical Calculationsmentioning

confidence: 99%

“…The property that is man ifested on passing from the neutral to the protonated form of 2SQ, the α effect has been mentioned above. 2 Styrylanthracene exhibits another interesting prop erty, the "one way" cis-trans photoisomerization reaction, when only the cis isomer is reactive (cistrans photoisomerization quantum yield is ϕ ct > 0), while the trans isomer does not undergo photoisomer ization (ϕ tc ~ 0) [4][5][6]. In the case of combination of the 2SQ and 2SA properties in 2SBQ, it might be expected that the trans isomer of 2SBQ would be pho toinert in the neutral form (as 2SA) and photoactive in the protonated form (as 2SQ) and, hence, the photo dynamic equilibrium would be shifted towards the trans isomer in the neutral form and towards the cis isomer in the protonated form.…”

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“…As has been mentioned above, 2SA (analogue of 2SBQ and 3SA) is character ized by the one way photoisomerization reaction. The quantum yield ϕ tc is 10 -4 -10 -3 [4], and the quantum yield of the reverse reaction is ϕ ct = 0.58-0.63 [4,6]; moreover, since the s trans conformer alone enters the reaction, it has ϕ ct ~1 and reaction proceeds via the adiabatic route [6]. The cis isomer of 2SA (s cis con former) undergoes photocyclization, ϕ cd = 0.10.…”

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Spectral and photochemical properties of isomeric styrylbenzoquinolines

Будыка

Поташова

2013

High Energy Chem

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Photochemical properties of the annelated 2 styrylquinoline (2SQ) derivatives 2 styryl benzo[g]quinoline (2SBQ) and 3 styrylbenzo[f]quinoline (3SBQ) and 3 styrylacridine (3SA) have been investigated by experimental and quantum chemical methods. It has been found that the trans isomer of 3SBQ undergoes the photoisomerization reaction with a quantum yield of ϕ tc = 0.19, which increases to 0.44 for the protonated form, with the fluorescence quantum yield decreasing from 0.74 to 0.09. In contrast, the trans isomers of 2SBQ and 3SA are photochemically inert in both neutral and protonated forms, ϕ tc < 10 -3 . Quantum chemical calculation by the PM3 method show that the difference in photochemical properties of 2SBQ and 3SBQ is due to the difference in the structure of frontier molecular orbitals, which, in turn, results in the difference of the shape of the potential energy surface of excited S 1 states. Comparison of the properties of 2SBQ and 3SBQ with those of 2SQ reveals size and topological effects in the photochemistry of aza dia rylethylenes.

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“…However, 1-(9-anthryl)-2-phenylethene(9-APE) executes efficient cis → trans photoisomerization but do not undergo reverse trans → cis photoisomerization. [1][2][3][4][5][6] The excitation energy is extensively localized in the large anthracene moiety so that the transoid geometry corresponds to energy minima in the excited potential energy surface. The energy barrier to C=C bond twisting is too high for t-9-APE to undergo trans → cis photoisomerization.…”

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Photochemistry of Anthrylethene Derivatives Containing Heteroaromatic Ring : Pyrrole and Indole Derivatives

2004

Bulletin of the Korean Chemical Society

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Diarylethenes are generally known to perform reversible photochemical cis-trans isomerization. However, 1-(9-anthryl)-2-phenylethene(9-APE) executes efficient cis → trans photoisomerization but do not undergo reverse trans → cis photoisomerization.1-6 The excitation energy is extensively localized in the large anthracene moiety so that the transoid geometry corresponds to energy minima in the excited potential energy surface. The energy barrier to C=C bond twisting is too high for t-9-APE to undergo trans → cis photoisomerization.Intramolecular charge transfer (ICT) could provide a way to lower the activation barrier to twisting of ethene bond in anthrylethene derivatives. Introduction of heteroaromatic ring into anthrylethene increases the dipole moment of the compound to initiate the excited state ICT processes.Nitrogen-heteroaromatic derivatives of 9-APE containing pyridine, 8,9 pyrazine, 10 or quinoline ring 11,12 in place of phenyl ring perform trans → cis photoisomerization as well as cis → trans photoisomerization, depending on the medium. In comparison with parent 9-APE, the aza substitution changes the donor-acceptor properties of the molecules. [8][9][10][11][12] Pyridine is referred to as an electron-deficient heterocycle and has some analogy with a benzene ring that carries an electron-withdrawing substituent. As pyridine, pyrazine, or quinoline ring acts as an electron acceptor, intramolecular charge transfer processes should affect on the excited state properties of nitrogen-heteroaromatic derivatives of 9-APE. As reported in our previous papers, 1-(9-anthryl)-2-(n-pyridyl)ethenes(n-APyE, n=2 or 4) 8 and 1-(9-anthryl)-2-(n-quinolyl)ethenes(n-AQE, n=2 or 4), 12 mono-aza analogues of 9-APE, show efficient trans → cis photoisomerization in polar solvent, and 1-(9-anthryl)-2-pyrazinylethene(APzE), 10 a di-aza analogue of 9-APE, exhibits transAEcis photoisomerization even in nonpolar solvent.On the other hand, pyrrole is referred to as an electron-rich heterocycle and has some analogy with a benzene ring that carries an electron-donating substituent. In this paper, we prepared 9-APE derivatives containing electron-rich pyrrole or indole ring and investigated their excited-state properties in comparison with electron-deficient pyridine derivative 4-APyE.Absorption and fluorescence spectra of t-2-APyrE, t-2-AIE, and t-2-AMIE in cyclohexane and acetonitrile are shown in Figure 1. Table 1 summarizes absorption and fluorescence data of t-2-APyrE, t-2-AIE, and t-2-AMIE along with those of t-9-APE and t-4-APyE. Absorption spectral shape and its maxima are not nearly influenced by the solvent polarity for all the compounds studied.In contrast to the absorption spectra, fluorescence maxima and quantum yields are strongly dependent on the solvent polarity as well as the kind of the heteroaromatic ring introduced into 9-APE. For a hydrocarbon t-9-APE, the fluorescence wavelength maxima and fluorescence quantum yields remain unchanged in the solvents of different polarity. However, a pyridine derivative t-4-APyE (s...

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A photophysical and theoretical study of styrylanthracenes

Cited by 49 publications

References 0 publications

9-[(E)-2-phenylethenyl]anthracene and 9-[(E)-2-(naphthalen-2-yl)ethenyl]anthracene as traps for singlet oxygen: photosensitized oxidation and photodynamic effect on Leishmania tarentolae parasites

9-[(E)-2-phenylethenyl]anthracene and 9-[(E)-2-(naphthalen-2-yl)ethenyl]anthracene as traps for singlet oxygen: photosensitized oxidation and photodynamic effect on Leishmania tarentolae parasites

Spectral and photochemical properties of isomeric styrylbenzoquinolines

Photochemistry of Anthrylethene Derivatives Containing Heteroaromatic Ring : Pyrrole and Indole Derivatives

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