81944-71-0Relevant academic research and scientific papers
Calix[4]crown in dual sensing functions with FRET
Lee, Seoung Ho,Sung, Kuk Kim,Ju, Han Bok,Suh, Hyun Lee,Yoon, Juyoung,Lee, Kilsung,Jong, Seung Kim
, p. 8163 - 8167 (2005)
A new calix[4]crown chemosensor based on dual sensing probes reveals Pb2+ ion selectivity over other metal ions, which arises from a hypsochromic shift of azo units in UV spectrum as well as a fluorescence enhancement of pyrenyl parts in fluore
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.
Solvatochromism of new substituted 4-[(E)-(4-nitrophenyl)diazenyl]phenolate dyes
de Melo, Carlos E.A.,Nicoleti, Celso R.,Nandi, Leandro G.,Schneider, Felipe S.S.,da S. Oliboni, Robson,Caramori, Giovanni F.,Machado, Vanderlei G.
, (2020/01/30)
Studies on the reverse solvatochromism of dyes in pure solvents are of interest to gain a better understanding of the nature of this phenomenon. In this paper, a series of nine compounds, exhibiting phenol and 4-nitrophenyl groups linked with an azo conjugated bridge, was synthesized and characterized. These compounds were deprotonated to generate solvatochromic phenolate dyes. The azo bridge makes the phenol more acidic, in comparison with the related compounds exhibiting a CH[dbnd]CH or CH[dbnd]N bridge in their molecular structure, indicating the electron withdrawing character of the azo bridge. The solvatochromism of the dyes was investigated in 29 solvents and their intense colors in solution were attributed to π-π* electronic transitions, with an intramolecular charge transfer from the phenolate towards the 4-nitroaryl group. The probes exhibited a reversal in their solvatochromism, in a similar fashion to the behavior verified with related dyes presenting CH[dbnd]CH or CH[dbnd]N as the conjugated bridge; however, the azo dyes are much less sensitive to solvent polarity changes. Multiparametric analysis showed that the azo dyes are very sensitive to the acidity of the medium, but still to a lesser degree than the corresponding imine and stilbene dyes, due to the electronegativity of the azo group. The reverse solvatochromism of the dyes is dictated by the electron-donor phenolate and by the electron-acceptor 4-nitroaryl groups, independently of the conjugated bridge, of the additional nitro group and of the nature of substituents in the 2,6-positions of the phenolate groups. Thus, the solvatochromic reversal verified represents a committed step involving the interaction of the nitro and phenolate groups in the probe with the molecules of structurally different solvents.
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.
Novel Phenyldiazenyl Fibrate Analogues as PPAR α/γ/δ Pan-Agonists for the Amelioration of Metabolic Syndrome
Giampietro, Letizia,Laghezza, Antonio,Cerchia, Carmen,Florio, Rosalba,Recinella, Lucia,Capone, Fabio,Ammazzalorso, Alessandra,Bruno, Isabella,De Filippis, Barbara,Fantacuzzi, Marialuigia,Ferrante, Claudio,MacCallini, Cristina,Tortorella, Paolo,Verginelli, Fabio,Brunetti, Luigi,Cama, Alessandro,Amoroso, Rosa,Loiodice, Fulvio,Lavecchia, Antonio
supporting information, p. 545 - 551 (2019/03/19)
The development of PPARα/γ dual or PPARα/γ/δ pan-agonists could represent an efficacious approach for a simultaneous pharmacological intervention on carbohydrate and lipid metabolism. Two series of new phenyldiazenyl fibrate derivatives of GL479, a previously reported PPARα/γ dual agonist, were synthesized and tested. Compound 12a was identified as a PPAR pan-agonist with moderate and balanced activity on the three PPAR isoforms (α, γ, δ). Moreover, docking experiments showed that 12a adopts a different binding mode in PPARγ compared to PPARα or PPARδ, providing a structural basis for further structure-guided design of PPAR pan-agonists. The beneficial effects of 12a were evaluated both in vitro, on the expression of PPAR target key metabolic genes, and ex vivo in two rat tissue inflammatory models. The obtained results allow considering this compound as an interesting lead for the development of a new class of PPAR pan-agonists endowed with an activation profile exploitable for therapy of metabolic syndrome.
Activation volumes for: Cis -to- trans isomerisation reactions of azophenols: A clear mechanistic indicator?
Garcia-Amorós, Jaume,Stopa, Grzegorz,Stochel, Grazyna,Van Eldik, Rudi,Martínez, Manuel,Velasco, Dolores
, p. 1286 - 1292 (2018/01/17)
The thermal cis-to-trans isomerisation reaction of a series of hydroxy-substituted azo derivatives was studied kinetico-mechanistically as a function of temperature and pressure in order to investigate the possible role of the solvent in controlling the isomerisation mechanism, viz. inversion versus rotation. The variation of the observed first order rate constants for kinetic runs carried out at different temperatures and pressures was used to determine the thermal activation parameters ΔH? and ΔS?, and the pressure activation parameter ΔV?. In addition, some experiments with deuterated species or solvents were also performed. The reported results could be interpreted as indicative of a changeover from an inversion mechanism for non-polar solvents to a rotational mechanism for polar solvents, capable of hydrogen bonding, for some of the systems studied. However, the operation of a rotational mechanism in all studied cases can account more consistently for the data observed.
Templated assembly of photoswitch Azobenzene (4-(4-nitrophenylazoyl)-phenol) by functionalization of multi-walled carbon nanotube for solar energy storage applications
Telgerafchi, Armaghan Ehsani,Mehranpour, Milad,Nazockdast, Hossein
, p. 113 - 116 (2018/07/31)
In order to provide global energy applications, solar energy resources will desire remarkable advances in solar energy technologies. In this paper, the novel synthesis of the functionalization of Multi-wall Carbon Nanotube(MWCNT) with Azobenzene molecule (4-(4-nitrophenylazoyl)-phenol) by esterification method was approached. The covalent bond of carbonyl was revealed in FTIR Test (Fourier-Transform Infrared Spectroscopy). Templating Azobenzene molecules on the side wall of MWCNT increased the stored energy per Azobenzene molecule and created hybrid Solar Thermal Fuels (STF). The DSC Test (Differential Scanning Calorimetry) showed that Solar Thermal Fuels composed of a photoswitchable molecules indicates significantly increased energy storage capabilities over the generation of a nano-templated structure.
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.]
