1435-60-5Relevant articles and documents
UV spectroscopic studies and charge transfer properties of azobenzene-containing cyclopentadienyliron complexes of arenes: A combined experimental and density functional theoretical study
Li, Guang Lei,Liu, Ji Qiang,Zhao, Bao Dong,Wang, Tao
, p. 287 - 291 (2013)
This study investigates the UV-Vis absorption and fluorescence emission of newly synthesized (η6-4-(4-nitrophenylazo) phenoxyl benzene) (η5-cyclopentadienyl) iron hexafluorophosphate (Fc-azo). Quantum chemical calculations of the orbital energy, geometrical structure, absorption spectra, and first hyperpolarizability (β) values of the Fc-azo were carried out using density functional (DFT/B3LYP and TD-DFT) methods. Comparisons between hydroxyl azobenzene compound and Fc-azo were made. Results showed that the observed spectra were in good agreement with the calculated values. The positive solvatochromism of the UV-Vis absorption of Fc-azo upon the increase in solvent polarity from the experiment and the calculated HOMO and LUMO energies showed that charge transfer occurred within the molecule. Moreover, the change in electron distribution led to the improved β for Fc-azo.
Ionic liquid 1-(3-trimethoxysilylpropyl)-3-methylimidazolium nitrite as a new reagent for the efficient diazotization of aniline derivatives and in situ synthesis of azo dyes
Valizadeh,Amiri,Shomali,Hosseinzadeh
, p. 495 - 501 (2011)
A new ionic liquid 1-(3-trimethoxysilylpropyl)-3-methylimidazolium nitrite was synthesized. This ionic liquid was used as a convenient nitrosonium source in diazotization of arylamines into their corresponding diazonium salts which were converted into their related azo dyes via the in situ azo-coupling with aniline derivatives or phenolic compounds. The diazotization of anilines in this ionic liquid and subsequent azo-coupling generated the related azo dyes in good to excellent yields at 0-5 °C in short reaction times via a simple experimental procedure.
Nonlinear optical effects in polymeric azoesters
Nadtoka, Oksana,Krupka, Oksana,Luk, Jerome,Syromyatnikov, Volodymyr,Sahraoui, Bouchta,Smokal, Vitaliy
, p. 302 - 309 (2008)
The methacrylic monomers containing azobenzene moiety with flexible alkyl spacers of different lengths and groups of different nature are synthesized, and their physicochemical properties were determined by electronic absorption, 1H NMR spectroscopy, and element analysis. In the present work, the homopolymers built with the use of the free radical polymerization of methacrylic monomers incorporating an azobenzene side-group have been synthesized and structurally characterized. The results of photochemical and optical activities of the corresponding polymers are presented. Third-order nonlinear optical (NLO) properties of the azopolymer solutions are studied by the degenerate four wave mixing (DFWM) method.
Stimuli responsive materials supported by orthogonal hydrogen and halogen bonding or i···alkene interaction
Frangville, Pierre,Gelbcke, Michel,Kumar, Shiv,Meyer, Franck,Van Hecke, Kristof
, (2021/12/24)
Smart materials represent an elegant class of (macro)-molecules endowed with the ability to react to chemical/physical changes in the environment. Herein, we prepared new photo responsive azobenzenes possessing halogen bond donor groups. The X-ray structures of two molecules highlight supramolecular organizations governed by unusual noncovalent bonds. In azo dye I-azo-NO2, the nitro group is engaged in orthogonal H···O···I halogen and hydrogen bonding, linking the units in parallel undulating chains. As far as compound I–azo–NH–MMA is concerned, a non-centrosymmetric pattern is formed due to a very rare I···π interaction involving the alkene group supplemented by hydrogen bonds. The Cambridge Structural Database contains only four structures showing the same I···CH2=C contact. For all compounds, an19F-NMR spectroscopic analysis confirms the formation of halogen bonds in solution through a recognition process with chloride anion, and the reversible photo-responsiveness is demonstrated upon exposing a solution to UV light irradiation. Finally, the intermediate I–azo–NH2 also shows a pronounced color change due to pH variation. These azobenzenes are thereby attractive building blocks to design future multi-stimuli responsive materials for highly functional devices.
Two-Phase Electrochemical Generation of Aryldiazonium Salts: Application in Electrogenerated Copper-Catalyzed Sandmeyer Reactions
Goljani, Hamed,Tavakkoli, Zahra,Sadatnabi, Ali,Nematollahi, Davood
supporting information, p. 5920 - 5924 (2020/08/12)
The electrochemical generation of aryldiazonium salts from nitroarenes in a two-phase system (ethyl acetate/water) was reported for the first time. Some compounds including azo, azosulfone, and arylazides were prepared in good yields with good purity. Cathodically generated aryldiazoniums and anodically produced copper(Ι) ions were used to perform Sandmeyer reactions. To improve the method, an H-type self-driving cell equipped with a Zn rod as an anode was introduced and used for two-phase aryldiazonium production.
Photoisomerization and Mesophase Formation in Azo-Ionic Liquids
Renier, Olivier,Bousrez, Guillaume,Stappert, Kathrin,Wilk-Kozubek, Magdalena,Adranno, Brando,Pei, Hanwen,Spielberg, Eike T.,Smetana, Volodymyr,Mudring, Anja-Verena
, p. 214 - 225 (2019/12/24)
Ionic liquids present a versatile, highly tunable class of soft functional materials. Aside from being low melting salts, they can be endowed with additional functionalities. In N-alkylimidazolium halides, which are a prominent class of ionic liquids (ILs), the imidazolium cation was linked via an ether-bridge to an azobenzene unit in order to obtain photoresponsive materials through photoinduced trans-cis isomerization. The azobenzene unit, in turn, was modified with electron-donating or -withdrawing groups such as methyl-, tert-butyl-, methoxy-, N,N-dimethylamino, and nitro groups to study their influence on the photoisomerization and phase behavior. Endowing the imidazolium additionally with a long alkyl chain allows the materials to potentially form liquid crystalline (LC) mesophases before melting into the isotropic liquid. All studied compounds qualify as ionic liquids, and all, except for the nitro-compound, show the formation of smectic mesophases melting to the isotropic liquid. The compounds with the bulkiest aliphatic substituent, the tert-butyl, shows the lowest melting point, the largest mesophase window, and an efficient photochemical trans-cis conversion (>90%). In summary, by tuning sterically and electronically the cationic part of ILs, a photoswitchable room temperature liquid crystal could be developed and design guidelines for photoresponsive ionic liquids could be obtained.
Can be alkaline dyeing of the bright yellow dispersion dye
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Paragraph 0129; 0130, (2017/12/07)
The invention discloses a bright yellow disperse dye capable of alkaline dyeing. The bright yellow disperse dye is a compound represented by a formula A, wherein R1 is -H, -CH3, -C2H5, -OCH3 or -OC2H5, and R2 is C1-C4 straight-chain or branched-chain alkyl or benzyl. The disperse dye shows a bright yellow color, can be used individually and also can be in combination use with alkali-resisting disperse dyes having other colors. The disperse dye has excellent alkali resistance and hydrogen peroxide oxidization resistance stability; the characteristic makes the disperse dye not only can be applied in general alkaline printing and dyeing processing of a polyester fiber material, but also can be applied in a scouring dyeing-bath process or a bleaching dyeing-bath process and a dispersed active one-paste printing process, and can meet the requirements of environmental protection.
Nano-CuFe2O4-supported sulfonic acid as a novel and recyclable nanomagnetic acid for diazotization of aromatic amines: efficient synthesis of various azo dyes
Nemati, Firouzeh,Elhampour, Ali,Natanzi, Mahshid B.,Sabaqian, Samaneh
, p. 1045 - 1054 (2016/05/02)
Abstract: A novel heterogeneous sulfonic acid functionalized nanomagnetic CuFe2O4 was successfully prepared and characterized by analyzing different obtained data including Fourier transform infrared spectroscopy, X-ray powder diffraction, field emission scanning electron microscopy, energy-dispersive X-ray spectroscopy, thermogravimetric analysis, dynamic light scattering and vibrating sample magnetometer. Then the novel acidic reagent was examined in synthesis of various azo-containing compounds from coupling of aryl diazonium ferrite sulfate salts with aromatic and non-aromatic compounds. The procedure starts by diazotization of aromatic amines with NaNO2 and wet CuFe2O4–SO3H and then coupling reaction of aryl diazonium ferrite sulfate salts with appropriate reagent. The prepared nano-solid acid showed high activity in synthesis of variety of aryl diazonium salts. In addition the as-prepared aryl diazonium ferrite sulfate salts are stable at room temperature for many hours and reacted efficiently in coupling reactions of aryl diazonium salts. All the azo dyes are synthesized in high yields and simple reaction conditions at room temperature. Moreover, the nanomagnetic solid acid was easily recovered from the reaction mixture and reused five runs without significant loss of activity. Graphical Abstract: [Figure not available: see fulltext.]
Phase Difference Plate, Laminated Polarizing Plate Using the Phase Difference Plate and Display Device Using the Phase Difference Plate
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Paragraph 0215-0217, (2016/11/14)
The present invention provides a phase difference plate, which inhibits the reduction of transmissivity to the minimum, has a desirable birefringent wavelength dispersion and an excellent reflecting angle of view characteristics, and a less fluctuation of dichroic ratio even under high temperature and humidity, and shows an improved optical reliability, a laminated polarizing plate using the same and a display device of viewing angle. According to the present invention, a birefringence of andDelta;n, as a phase difference plate having a characteristic of negative dispersion which becomes larger as a measuring wavelength is longer in at least some wavelength area of visible ray areas, comprises a polymerizable liquid crystal composition and a polymer formed by polymerizing one or more polymerizable dichroic dyes. In addition, provided is a phase difference plate in which a liquid crystal compound is formed with a liquid crystal film aligned with a nematic hybrid.(AA) andDelta;n of embodiment 1(BB) Ideal graph(CC) Wavelength (nm)COPYRIGHT KIPO 2016
Synthesis and characterization of azobenzene-based gold nanoparticles for photo-switching properties
Biswas, Tapan Kumar,Sarkar, Shaheen M.,Yusoff, Mashitah M.,Rahman, Md Lutfor
, p. 231 - 237 (2016/02/23)
A series of new azobenzene based thiolated liquid crystals modified with gold nanoparticles were synthesized and characterized using a different mode of delegated tools e.g. FTIR, NMR and FESEM-EDX measurements for the structural properties of synthesized compounds. Polarized optical microscopy studies have revealed all the studied compounds having liquid crystalline properties, as a typical nematic phase. These liquid crystal capped gold nanoparticles' size was determined by TEM experiment. In addition, azobenzene-based gold nanoparticles containing flexible spacers showed photochromic behavior upon UV irradiation. These molecules exhibited strong photoisomerisation behavior in solutions and their trans to cis isomerisation took about 44 s whereas the reverse process almost took place ranging from 82 to 125 min.
