The Polarized Absorption Spectra of Some α-Aminoanthraquinones

Inoue, Hiroyasu; Hoshi, Toshihiko; Yoshino, Junko; Tanizaki, Yoshié

doi:10.1246/bcsj.45.1018

Cited by 72 publications

(30 citation statements)

References 8 publications

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“…The electron density for HOMO and LUMO of each species is shown in Figure 8. The calculated electron density of HOMO-LUMO transition for DO11 agrees with the computational results for aminoanthraquinones in the literature [60,63]: the amine group is the principal electron donor of the ICT, and the electron acceptors include both carbonyl groups, the center ring and the unsubstituted ring. However, while the amine group remains the principal electron donor of the ICT for all reversibly-and irreversibly-damaged species, the carbonyl group adjacent to the amine group loses its electron accepting ability even though the other electron acceptors are unchanged in their electron accepting ability.…”

Section: Computational Resultssupporting

confidence: 82%

Spectroscopic studies of the mechanism of reversible photodegradation of 1-substituted aminoanthraquinone-doped polymers

Hung

Bhuyan

Schademan

et al. 2016

The Journal of Chemical Physics

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The mechanism of reversible photodegradation of 1-substituted aminoanthraquinones doped into poly(methyl methacrylate) and polystyrene is investigated. Time-dependent density functional theory is employed to predict the transition energies and corresponding oscillator strengths of the proposed reversibly-and irreversibly-damaged dye species. Ultraviolet-visible and Fourier transform infrared (FTIR) spectroscopy are used to characterize which species are present. FTIR spectroscopy indicates that both dye and polymer undergo reversible photodegradation when irradiated with a visible laser. These findings suggest that photodegradation of 1-substituted aminoanthraquinones doped in polymers originates from interactions between dyes and photoinduced thermally-degraded polymers, and the metastable product may recover or further degrade irreversibly. INTRODUCTIONOrganic materials have a broad range of applications such as high-resolution fluorescence microscopy [1][2][3][4][5][6][7], second harmonic generation (SHG) microscopy [8][9][10][11][12], dye sensitized and polymer solar cells [13][14][15][16][17], solid state dye/organic lasers [18][19][20], and organic light emitting diodes [21,22], to name a few. Photostability of organic compounds and polymers is often a requirement for applications incorporating light-matter interaction [2-4, 6, 8, 18-20, 23-30]. When a material undergoes photodegradation, its characteristic properties deteriorate over time, which is referred to as decay; the reverse change in the characteristic properties of the material is referred to as recovery. Though photodegradation is often irreversible, the recovery process has been observed from a large variety of materials, typically involving polymers and often together with dyes, with various experimental techniques when the photodegraded materials are kept in dark for a long enough time, typically hours to days [30][31][32][33][34][35][36][37][38][39][40][41][42][43][44].Amplified spontaneous emission (ASE) of disperse orange 11 (DO11) doped in poly(methyl methacrylate) (PMMA) bulk sample was observed to fully recover in the dark about 40 hours after photodegradation when irradiated with a 532 nm second harmonic Nd:YAG picosecond laser [33]. This self-healing phenomenon was also observed in various anthraquinone derivatives doped in PMMA and polystyrene (PS) thin films [41,42] and DO11 doped in MMA-styrene copolymers thin films [42,45] probed with transmittance image microscopy and ASE. The photodegraded thin film samples are often observed to recover partially, which suggests there exists both reversible and irreversible photodegradation. The lack of evidence for linear dichroism during photodegradation measurements eliminates orientational hole burning as the mechanism causing reversible photodegra- [38,42,46,[50][51][52][53][54], they have failed to elucidate the underlying mechanism.Several hypotheses of the mechanism responsible for reversible photodegradation in DO11/PMMA have been proposed, including intramolecular proton transfer and ...

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Section: Computational Resultssupporting

confidence: 82%

Spectroscopic studies of the mechanism of reversible photodegradation of 1-substituted aminoanthraquinone-doped polymers

Hung

Bhuyan

Schademan

et al. 2016

The Journal of Chemical Physics

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“…orgunic solvents The uv and visible absorption spectra of AAQ dyes (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19) in ethanol display six absorption bands A, B,C, D, E,andFlocatednear210,230,245,275, 308, and 4.50-560nm respectively. The band A suffers a blue shift as the polarity of the solvent increases and disappears in HCl solution.…”

Section: Results and Discussion I Electronic Absorption Spectra In mentioning

confidence: 99%

“…It was previously assigned to n-n* transitions (17). Inoue et al (10) assigned this band as due to intramolecular CT from the amino group to the carbonyl group without indicating the type of this CT. El-Ezaby et al (8) observed this band in the spectra of hydroxy-anthraquinone dyes and attributed it to C T (from the effect of solvent on its position). To give a precise assignment of the band F, the energy of this band may be calculated theoretically and experimentally for the dyes 1 and 2 containing one amino group.…”

Section: Results and Discussion I Electronic Absorption Spectra In mentioning

confidence: 99%

“…The remainder of the investigated dyes (7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19), as listed below, were carefully prepared for the first time 'Author to whom all correspondence should be addressed. ZRevision received September 11, 1981. absorption spectra were recorded in nine Spec.…”

Section: Experimental M E Preparation and Purijcationmentioning

confidence: 99%

“…The effect of solvents on the absorption spectra of hydroxy-and aminoanthraquinone dyes have also been studied (6)(7)(8). In addition, the electronic absorption spectra of anthraquinone and its amino derivatives have been studied (3,9,10) by means of the polarized absorption spectra on stretched PVA sheets and by means of theoretical calculations.…”

Section: Introductionmentioning

confidence: 99%

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Spectral behaviour and solvent effects of some aminoanthraquinone dyes

Etaiw¹,

Sekkina²,

El-Hefnawey³

et al. 1982

Can. J. Chem.

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The electronic absorption spectrum of each of nineteen AAQ dyes has been studied in nine different organic solvents. The acid dissociation constants of dyes containing OH, COOH, or SO3H groups have also been determined experimentally. The spectra in ethanol display five bands in the uv region and one in the visible region (450–560 nm). This band is assigned to CT transitions of the type l–aπ which result from the interaction of the lone pair of the nitrogen atom with the phenyl ring of the carbonyl group. The CT nature of the band was supported theoretically and by the effect of solvent on band position.

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