Vibrational analysis of [4-[(E)-phenylazo] phenyl]ethanol based on the comparison between the experimental and DFT calculated Raman spectra

Minisini, Benoît; Messager, G.; Piyanzina, Irina; Delorme, Nicolas; Bardeau, Jean‐François

doi:10.1134/s0022476614050072

Cited by 6 publications

(6 citation statements)

References 63 publications

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“…The latter spectra perfectly match the spectrum published for such a solution of ca. 10 −5 mol L −1 concentration, 36 which should correspond mainly to monomeric DO3 solvated by chloroform. Moreover, Raman spectrum quantum chemically simulated for isolated DO3 molecule perfectly matches both the published and our own spectra registered for the diluted solutions of DO3 (Figure 4).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…Raman spectra of DO3: the simulated spectra of monomer and dimers with head-to-tail (a), parallel (b), shifted parallel (c), and antiparallel (d) arrangement are scaled according to ref : ν scaled = A ν computed + B , where A = 0.9395 and B = 55.36 cm –1 . Experimental spectra of the powder sample (2) and the solution in CHCl 3 of c ∼ 10 –2 mol L –1 (1).…”

Section: Resultsmentioning

confidence: 99%

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Supramolecular Organization of Solid Azobenzene Chromophore Disperse Orange 3, Its Chloroform Solutions, and PMMA-Based Films

et al. 2018

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Quantum chemical modeling in combination with vibrational and electronic absorption spectroscopy has delivered detailed information about supramolecular organization of azochromophore 4-amino-4′-nitroazobenzene (DO3), its solutions, and blends with poly(methyl methacrylate) (PMMA) polymer of various concentrations. It is shown that the neat chromophore contains both antistacked forms and hydrogen bonded associations of the "head-to-tail" type, while separate DO3 molecules dominate in diluted solutions of DO3 in chloroform. In PMMA/DO3 films with low concentrations of the chromophore, DO3 is mainly Hbonded to CO moieties of PMMA matrix, while in the blends with high concentrations of DO3 molecules, the latter form hydrogen bonds both with PMMA and with each other. Infrared, Raman, and UV−vis spectroscopic markers of isolated DO3 molecules and various modes of their supramolecular associations are revealed.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Supramolecular Organization of Solid Azobenzene Chromophore Disperse Orange 3, Its Chloroform Solutions, and PMMA-Based Films

et al. 2018

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“…Figure a shows a change in the asymmetric CC stretching band of the nitro containing phenyl ring of DR1, which was found to exhibit the most sensitive shift of all bonds in the system through this exchange and aggregation process. This band is centered on 1390 cm −1 in the case of pure DR1, and also displays a shouldering red‐shifted by about 10 cm −1 . The Raman spectrum of the “wet” 10% PVP/DR1 displays a similar profile.…”

Section: Resultsmentioning

confidence: 93%

“…Other bands also display modest shifts, which are consistent with the changes described above. The coupling band of the stretching phenyl-nitrogen and in-plane CH deformation, assigned to the 1140 cm −1 band, [33] is blue shifted by about 3 cm −1 when comparing the dry and wet spectra of the 10% DR1/PVP and the overloaded 75% w/w. The symmetric stretching band of the nitro group also shows a similar shift, but is red shifted.…”

Section: Resultsmentioning

confidence: 99%

The Orange Side of Disperse Red 1: Humidity‐Driven Color Switching in Supramolecular Azo‐Polymer Materials Based on Reversible Dye Aggregation

Schoelch

Vapaavuori

Rollet

et al. 2016

Macromol. Rapid Commun.

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Humidity detection, and the quest for low-cost facile humidity-sensitive indicator materials is of great interest for many fields, including semi-conductor processing, food transport and storage, and pharmaceuticals. Ideal humidity-detection materials for a these applications might be based on simple clear optical readout with no power supply, i.e.: a clear color change observed by the naked eye of any untrained observer, since it doesn't require any extra instrumentation or interpretation. Here, the introduction of a synthesis-free one-step procedure, based on physical mixing of easily available commercial materials, for producing a humidity memory material which can be easily painted onto a wide variety of surfaces and undergoes a remarkable color change (approximately 100 nm blue-shift of λ ) upon exposure to various thresholds of levels of ambient humidity is reported. This strong color change, easily visible to as a red-to-orange color switch, is locked in until inspection, but can then be restored reversibly if desired, after moderate heating. By taking advantage of spontaneously-forming reversible 'soft' supramolecular bonds between a red-colored azo dye and a host polymer matrix, a reversible dye 'migration' aggregation appearing orange, and dis-aggregation back to red can be achieved, to function as the sensor.

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“…Various experimental and theoretical studies on the structure, tautomeric behavior, dyeing properties, and vibrational analysis of azo dyes [10][11][12][13][14][15][16][17][18][19] and their metal complexes [20][21][22] have been done. Due to their chemical significance and spectroscopic properties, hetarylazo dyes were studied extensively by spectroscopic and theoretical methods.…”

Section: Introductionmentioning

confidence: 99%

Hetarylazopyrazolone Dyes Based on Benzothiazole and Benzimidazole Ring Systems: Synthesis, Spectroscopic Investigation, and Computational Study

Aktan

Uyar

2017

Journal of Chemistry

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In this study, the synthesized coupling component 1-(2-benzothiazolyl)-3-methylpyrazol-5-one reacted with diazotised heterocyclic amines to afford six novel hetarylazopyrazolone dyes. These azo dyes based on benzothiazole and benzimidazole ring systems were characterized by spectral methods and elemental analyses. The solvatochromic behaviors of these dyes in various solvents were evaluated. The ground state geometries of the dyes were optimized using density functional theory (DFT). Solvent, acid-base, and substituent influences on the wavelength of the maximum absorption were examined in detail. Time-dependent density functional theory (TD-DFT) calculations were performed to obtain the absorption spectra of the dyes in various solvents and the results compared with experimental values. Besides, frontier molecular orbitals (FMO) analysis for the dyes is also described from the computational process.

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Vibrational analysis of [4-[(E)-phenylazo] phenyl]ethanol based on the comparison between the experimental and DFT calculated Raman spectra

Abstract: UDC 543.422:548.737 In this work we assessed the performance of the density functional theory (DFT) approach through a comparison study with the experimental Raman spectrum obtained for

Cited by 6 publications

References 63 publications

Supramolecular Organization of Solid Azobenzene Chromophore Disperse Orange 3, Its Chloroform Solutions, and PMMA-Based Films

Supramolecular Organization of Solid Azobenzene Chromophore Disperse Orange 3, Its Chloroform Solutions, and PMMA-Based Films

The Orange Side of Disperse Red 1: Humidity‐Driven Color Switching in Supramolecular Azo‐Polymer Materials Based on Reversible Dye Aggregation

Hetarylazopyrazolone Dyes Based on Benzothiazole and Benzimidazole Ring Systems: Synthesis, Spectroscopic Investigation, and Computational Study

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