Red shifts in the spectra of anthracene derivatives

Veljković, S.R.

doi:10.1039/tf9575301181

Cited by 10 publications

(5 citation statements)

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“…Setting I e ≈ I g , N. G. Bakhshiev et al [6] determined the change in the polarizability ∆α eg for a number of compounds according to relation (3). For anthracene, it was 15 Å 3 for a O = 6 Å, which is also consistent with the value 16.7 Å 3 obtained by the Stark spectroscopy method [11].…”

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confidence: 67%

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Dispersion interactions, electronic absorption spectra of anthracenes in polar glassy media at 77–300 K, and the change in polarizability upon excitation

Pavlovich

2007

J Appl Spectrosc

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The effect of dispersion interactions on the electronic spectra of organic compounds is analyzed within second-order perturbation theory. A formula is obtained which makes is possible to determine the change in the polarizability of the molecules upon excitation, ∆α eg , using data on the effect of the bulk polarizability P n of the solvent on the position of the electronic spectrum. It is shown that when the solutions are cooled, the long-wavelength shift of the absorption spectra for the studied anthracenes in alcohols is mainly due to dispersion interactions and is caused by an increase in P n . The possibility of using the new formula for ∆α eg is demonstrated for anthracenes as an example. It is found that for anthracene, 1-chloroanthracene, 9,10-dichloroanthracene, 9,10-dibromoanthracene, 9,10-diiodoanthracene ∆α eg is 16.5, 16.9, 17.2, 18.6, and 20.2 Å 3 respectively.

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confidence: 67%

“…Temperature dependence of the integrated absorption for DIA in ethanol (1), isobutanol(2), and isopropanol(3). The solid line is the linear approximation of the experimental data (1), obtained in the absence of scattering.…”

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confidence: 99%

Dispersion interactions, electronic absorption spectra of anthracenes in polar glassy media at 77–300 K, and the change in polarizability upon excitation

Pavlovich

2007

J Appl Spectrosc

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“…In the case of 9cyanoanthracene the wave length shift is in the opposite direction from anthracene and its other derivatives, i.e., the red shift is inversely proportional to the polar-izability of the solvent. This was ascribed (165) to a polar-polar interaction between solvent and 9-cyanoanthracene; such interaction would cancel out dispersion force interactions and hence the observed effect. On the other hand, 9-oximinoanthracene which contains the polar oximino group does not show the same fluorescence solvent effect observed for the cyano compound and it is possible that in this case hydrogen bonding takes place between solute and solvent (165).…”

Section: Anthracene and Derivativesmentioning

confidence: 95%

“…The fluorescence red shift in different solvents was examined more recently (165) for anthracene and several substituted anthracenes in 19 different solvents. The shifts were ascribed, as concluded earlier by Forster (53, p. 135), to dispersion forces.…”

Section: Anthracene and Derivativesmentioning

confidence: 99%

Effects of the Environment on the Fluorescence of Aromatic Compounds in Solution.

Duuren¹

1963

Chem. Rev.

130

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“…(4) and the residual effect of intersystem crossing activation processes at T = 77 K. Anthracene and its meso-substituted derivatives have point symmetry D 2h and variable dipole moments. Therefore, it was expected that nonspecific interactions would be the main reason for the shift of absorption spectra of anthracenes upon changing the solvent [16][17][18]. The bathochromic shift of the spectral bands for anthracene and its halogenated derivatives, including DIA, upon cooling glassified alcohol solutions is clearly evident [4].…”

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Absorptivity and fluorescence properties of 9,10-diiodoanthracene in solutions

et al. 2008

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The molar extinction coefficient, oscillator strength, natural fluorescence lifetime, and fluorescence quantum yield have been determined for 9,10-diiodoanthracene in ethanol at 20 o C. The temperature effect on the quantum yield was studied in the range 120-300 K. The fluorescence lifetime was measured at 77 K. During glassification of ethanol, the fluorescence intensity of 9,10-diiodoanthracene increases by more than 50 times due to the activation nature of the intersystem crossing from the S 1 ( 1 B 2u + ) state. The activation energy and pre-exponential factor for the probability of the intersystem S 1 ( 1 B 2u + ) L T n ( 3 B 3u + )-crossing are found. The long-wavelength shift of the absorption spectrum with increasing bulk polarizability of the solvent is interpreted as evidence of changes in the nonspecific interactions.Introduction. 9,10-Diiodoanthracene (DIA) is one of the least studied halogenated anthracenes. Its synthesis and certain spectral-luminescence properties of its solutions have been reported [1][2][3]. The influence of temperature on absorption spectra in glassified solvents (alcohols) has been investigated [4]. Combination scattering, absorption, and fluorescence spectra of crystals under hydrostatic pressure have been published [5]. Its tendency to undergo photodecomposition, which is especially strong in solvents such as hexane and CCl4, and its low solubility in alcohols create definite experimental difficulties. This probably explains the few publications dedicated to the optical properties of DIA. The basic spectral-luminescence properties of anthracene and its halogenated derivatives are well known and have been reviewed [6,7] and included in handbooks [8]. The goal of our work was to expand the list of anthracenes in tables by adding DIA to them. The investigations are timely because DIA can be used as an effective synthesizer of singlet oxygen. DIA also provides an example of a compound with a clearly evident internal heavy-atom effect. The positions of the absorption and fluorescence bands, the molar extinction coefficient, the fluorescence quantum yield at room temperature, and the fluorescence lifetime at 77 K were obtained directly from measurements and by processing the data. The natural fluorescence lifetime, oscillator strength, and activation energy and pre-exponential factor that characterize intersystem crossing from the S 1 -state were calculated using formulas described in known models.Experimental. Absorption spectra were measured on a Cary 500 spectrophotometer; fluorescence spectra, on a SOLAR SFL-1211A spectrofluorimeter (Minsk). Solutions were not degassed. The quantum yield was determined by a relative method. The standard was a solution of 3,6-diamino-N-methylphthalimide (sublimed) in ethanol with a yield of 0.46 [9]. A custom cryostat stabilized the temperature to within ±1 K as measured by a nichrome-copper thermocouple accurate to ±0.5 K. The fluorescence decay kinetics were measured by correlated photon counting using a TCC900 computer module (Edinburgh Instr...

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Red shifts in the spectra of anthracene derivatives

Cited by 10 publications

References 0 publications

Dispersion interactions, electronic absorption spectra of anthracenes in polar glassy media at 77–300 K, and the change in polarizability upon excitation

Dispersion interactions, electronic absorption spectra of anthracenes in polar glassy media at 77–300 K, and the change in polarizability upon excitation

Effects of the Environment on the Fluorescence of Aromatic Compounds in Solution.

Absorptivity and fluorescence properties of 9,10-diiodoanthracene in solutions

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