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

Burganov, Timur I.; Katsyuba, Sergey A.; Vakhonina, Tatyana A.; Sharipova, Anastasiya V.; Fominykh, Olga D.; Balakina, Marina Yu.

doi:10.1021/acs.jpcc.7b10543

Cited by 13 publications

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References 34 publications

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“…The application of density functional theory (DFT) calculations made it possible to study the effect of stacked dimer formation on the quadratic NLO response of azochromophores . The joint approach combining DFT calculations and vibrational and electronic absorption spectroscopy provided detailed information about the supramolecular organization of azochromophore Disperse Orange ( DO3 ), its solutions, and blends of composite material based on the poly(methyl methacrylate) polymer with various chromophore content . However, the theoretical study of the effect of formation of elongated head‐to‐tail aggregates of azochromophores was missing.…”

Section: Introductionmentioning

confidence: 93%

Effect of dimer formation via hydrogen bonding on static and dynamic nonlinear optical characteristics of chromophores

Shalin

Fominykh

Balakina

2019

Int J of Quantum Chemistry

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The effect of head-to-tail azochromophore dimer formation on the values of static and dynamic first hyperpolarizability is studied on the basis of calculations performed at M06-2X/aug-cc-pVDZ and ωB97X-D/aug-cc-pVDZ computational levels; the results are compared with those obtained at second-order Moller-Plesset pertubation theory (MP2)/aug-cc-pVDZ. Azochromophores DO3 and AAB-DCV, participating in the dimer formation, contain nitro-or dicyanovinylene acceptor moieties. The structure of the studied dimers is obtained at the B3LYP-D3/6-31++G (d,p) level with basis set superposition error (BSSE) correction. Dynamic first hyperpolarizabilities are calculated at radiation frequencies of 0.65 eV, 0.918 eV and 1.165 eV. The essential effect of dimer formation is demonstrated: it results in almost a 3.5 times increase of the first hyperpolarizability. In the series D1-D2-D3, β(2ω) values at 0.65 eV increase in a way similar to the static case: β(2ω) for D2 and D3 are 1.5 and 1.8 times higher than that for D1. The notable resonance enhancement of β(2ω) for the studied hydrogen-bonded dimers is demonstrated at radiation frequency of 1.165 eV. K E Y W O R D S azochromophore, chromophore dimer, hydrogen bonding, static and dynamic first hyperpolarizability 1 | INTRODUCTION The formation of supramolecular aggregates of organic push-pull chromophores and its effect on the nonlinear optical (NLO) response presents a relatively new direction in the field of new polymer NLO materials development. The establishment of supramolecular structure-property relation-ships can provide new insight into the design of such materials. [1,2] Various types of supramolecular aggregates were indicated in both experimental and theoretical research. [3,4] The first one is the chromophore clusters of the "head-to-tail" type, in which electron donor groups of one chromophore interact with the electron acceptor groups of the other one via hydrogen bonds (H-bonds); such an arrangement results in the essential enhancement of the NLO response with cooperative effect. [3][4][5][6][7][8][9] Another type of chromophores self-organization is represented by the π-stacked structures with either codirected or antiparallel dipole moments of chromophores; [3,4,[10][11][12][13] the latter case is characterized by vanishing NLO activity due to chromophores' centrosymmetric arrangement. In the codirected structures, the chromophores are shown to be mutually shifted, such that the shift degree determines the NLO characteristics of such structures. For the clusters with strongly shifted chromophores, a moderate increase of the molecular NLO response is predicted. [11,12] Atomistic modeling of chromophore-containing polymer materials allowed us to show the possibility of the formation of chromophore clusters of a different structure: both head-to-tail and stacked dimers. [14][15][16] The application of density functional theory (DFT) calculations made it possible to study the effect of stacked dimer formation on the quadratic NLO response of azochromophores. [12] The...

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Section: Introductionmentioning

confidence: 93%

Effect of dimer formation via hydrogen bonding on static and dynamic nonlinear optical characteristics of chromophores

Shalin

Fominykh

Balakina

2019

Int J of Quantum Chemistry

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“… 6 − 8 , 10 − 14 Both interactions among polymer chains and those involving host–guest pairs can contribute to the stabilization of the final material architecture. 7 , 11 As guest molecules, azobenzenes with a push–pull character (i.e., π-conjugated azobenzene units bearing electron-donor and electron-acceptor substituents) are attractive candidates. 7 , 8 , 10 , 12 − 15 …”

Section: Introductionmentioning

confidence: 99%

“…In this case, the macroscopic orientation of the active molecules is generally achieved by electric poling above the polymer glass transition temperature T g > T amb , and it is then frozen at ambient temperature. 6 , 7 In such systems, NLO performances such as second harmonic generation have been demonstrated. 8 , 9 Polymers containing NLO dyes are of great interest due to several advantages, such as: (i) they are cost-effective and easy to process; (ii) organic materials are easy to tailor to meet specific application requirements; and (iii) they are compatible with existing semiconductor technologies.…”

Section: Introductionmentioning

confidence: 99%

“… 7 , 11 As guest molecules, azobenzenes with a push–pull character (i.e., π-conjugated azobenzene units bearing electron-donor and electron-acceptor substituents) are attractive candidates. 7 , 8 , 10 , 12 − 15 …”

Section: Introductionmentioning

confidence: 99%

“…The DO3 dye exhibits a strong charge separation induced by its electron-withdrawing nitro group and electron-donor amino group, and it has been recently proposed for NLO applications in blends with polymers. 7 , 10 In these works, infrared (IR) and Raman vibrational spectroscopies have allowed for a deep study of the relevant role of the intermolecular interactions between the DO3 dye and the host polymer matrix.…”

Section: Introductionmentioning

confidence: 99%

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Morphology and Intramolecular Interactions in P(VDF-TrFE) Electrospun Nanofibers Doped with Disperse Orange 3 Dye: A Joint Infrared Spectroscopy and Electron Microscopy Study

et al. 2022

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In this study, we describe a host–guest system consisting of a push–pull dye, the 4-amino-4′-nitroazobenzene (Disperse Orange 3, DO3 ), mixed with the copolymer poly(vinylidene fluoride-co-trifluoroethylene) [ P(VDF-TrFE) ] as a potential candidate for nonlinear optics (NLO) applications. We developed electrospun nanofibers of the polymer/dye blend, showing a highly anisotropic molecular structure, where DO3 molecules are mostly oriented parallel to the polymer chain, running in the fiber axis direction. The technique opens a way for obtaining non-centrosymmetric ordering of the NLO chromophore without requiring further poling. The supramolecular architecture is deeply investigated through infrared vibrational spectroscopy, which allows detecting a new phase involving DO3 molecules linked together by strong directional H-bonds. Electron microscopies highlight peculiar nanofiber morphologies with a preferred localization of DO3 at the surface layers.

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Light‐Responsive Polyblend Films with Reconfigurable Surface Micropatterns as Rewritable Information Storage Media

et al. 2022

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Comprehensive Summary Stimulus‐sensitive surfaces with tunable morphologies exhibit a wide range of applications in the fields of surface science and engineering. Herein, a cost‐effective yet practical strategy is proposed to fabricate photo‐sensitive patterning surface on film/substrate wrinkle system based on an azo‐containing polyblend. By manipulating the stress field of the bilayer system globally and/or locally upon the stress relaxation triggered by the reversible cis‐trans isomerization of the azobenzene, heating/cooling triggered surface wrinkles on the polyblend films could be tailor‐made with visible‐light‐irradiation. Notably, upon selective photo‐irradiation, bespoke surface patterns may be cyclically generated or eliminated, allowing these reconfigurable patterned polyblend surfaces to be used as rewritable information storage media for non‐ink printing. The as‐prepared photo‐printed information patterns with high‐resolution are shown to be rewritable for multiple cycles and legible for over 90 d in dark ambient conditions. This study not only provides a versatile strategy for flourishing the stimulus‐sensitive systems, but also sheds light on the stress relaxation‐triggered morphological evolution of the wrinkling polyblend films.

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

Cited by 13 publications

References 34 publications

Effect of dimer formation via hydrogen bonding on static and dynamic nonlinear optical characteristics of chromophores

Effect of dimer formation via hydrogen bonding on static and dynamic nonlinear optical characteristics of chromophores

Morphology and Intramolecular Interactions in P(VDF-TrFE) Electrospun Nanofibers Doped with Disperse Orange 3 Dye: A Joint Infrared Spectroscopy and Electron Microscopy Study

Light‐Responsive Polyblend Films with Reconfigurable Surface Micropatterns as Rewritable Information Storage Media

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