- Construction of stable polymeric vesicles based on azobenzene and beta-cyclodextrin grafted poly(glycerol methacrylate)s for potential applications in colon-specific drug delivery
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Polymeric vesicles constructed from cyclodextrin- and azobenzene-grafted poly(glycidyl methacrylate)s showed excellent stability owing to the multiple host-guest complexation. Upon culturing in Na2S2O4-contained buffer sol
- Gu, Wen-Xing,Li, Qing-Lan,Lu, Hongguang,Fang, Lei,Chen, Qixian,Yang, Ying-Wei,Gao, Hui
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Read Online
- Unraveling the surface properties of PMMA/azobenzene blends as coating films with photoreversible surface polarity
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Various reports demonstrated that azobenzene derivatives are the chromophore of choice in photoresponsive surfaces showing reversible surface polarity. Hitherto the surface study of coating films based on polymer/azobenzene blends using contact angle meas
- Hisham, Shameer,Muhamad Sarih, Norazilawati,Tajuddin, Hairul Anuar,Zainal Abidin, Zul Hazrin,Abdullah, Zanariah
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p. 15428 - 15437
(2021/05/19)
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- Azobenzene derivative, solar thermal energy fuel film composite material and preparation method and application thereof
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The invention relates to an azobenzene derivative, a solar thermal energy fuel film composite material and a preparation method and application thereof, discloses a series of azobenzene derivatives, and provides a method for preparing a photo-induced phase change ready-to-use solar thermal energy fuel film through the azobenzene derivatives. The prepared solar thermal energy fuel composite film has good mechanical flexibility, photoisomerization effect and energy storage capacity. The composite film can rapidly generate cis-trans isomerization to store energy under the irradiation of an ultraviolet lamp, the stored energy is gradually increased along with the prolonging of irradiation time, the full state can be achieved within about 2 hours, the energy density can reach 200 J/g or above,and the temperature of the composite film can be continuously increased by about 5 DEG C. The charging/discharging process has very good reversibility, and no obvious attenuation exists after the energy is circularly charged/discharged for more than 5 times. The composite material has the advantages of simple preparation process, environmental friendliness, easily available materials, large heat release amount, good mechanical flexibility, strong acid and alkali corrosion resistance, good recycling performance and the like.
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Paragraph 0046-0047
(2021/03/30)
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- Photoisomerization and Mesophase Formation in Azo-Ionic Liquids
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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.
- Renier, Olivier,Bousrez, Guillaume,Stappert, Kathrin,Wilk-Kozubek, Magdalena,Adranno, Brando,Pei, Hanwen,Spielberg, Eike T.,Smetana, Volodymyr,Mudring, Anja-Verena
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p. 214 - 225
(2019/12/24)
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- Effects of Spacers on Photoinduced Reversible Solid-to-Liquid Transitions of Azobenzene-Containing Polymers
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Photoisomerization in some azobenzene-containing polymers (azopolymers) results in reversible solid-to-liquid transitions because trans- and cis-azopolymers have different glass transition temperatures. This property enables photoinduced healing and proce
- Weis, Philipp,Hess, Andreas,Kircher, Gunnar,Huang, Shilin,Auernhammer, Günter K.,Koynov, Kaloian,Butt, Hans-Jürgen,Wu, Si
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supporting information
p. 10946 - 10953
(2019/08/02)
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- Kinetic Control of a Self-Assembly Pathway towards Hidden Chiral Microcoils
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Manipulating the self-assembly pathway is essentially important in the supramolecular synthesis of organic nano- and microarchitectures. Herein, we design a series of photoisomerizable chiral molecules, and realize precise control over pathway complexity with external light stimuli. The hidden single-handed microcoils, rather than the straight microribbons through spontaneous assembly, are obtained through a kinetically controlled pathway. The competition between molecular interactions in metastable photostationary intermediates gives rise to a variety of molecular packing and thereby the possibility of chirality transfer from molecules to supramolecular assemblies.
- Guo, Yongxian,Liu, Yin,Gong, Yanjun,Xiong, Wei,Zhang, Chuang,Zhao, Jincai,Che, Yanke
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supporting information
p. 7463 - 7468
(2019/05/16)
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- Structure modification of an active azo-compound as a route to new antimicrobial compounds
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Some novel (phenyl-diazenyl)phenols 3a-g were designed and synthesized to be evaluated for their antimicrobial activity. A previously synthesized molecule, active against bacteria and fungi, was used as lead for modifications and optimization of the structure, by introduction/removal or displacement of hydroxyl groups on the azobenzene rings. The aim of this work was to evaluate the consequent changes of the antimicrobial activity and to validate the hypothesis that, for these compounds, a plausible mechanism could involve an interaction with protein receptors, rather than an interaction with membrane. All newly synthesized compounds were analyzed by 1H-NMR, DSC thermal analysis and UV-Vis spectroscopy. The in vitro minimal inhibitory concentrations (MIC) of each compound was determined against Gram-positive and Gram-negative bacteria and Candida albicans. Compounds 3b and 3g showed the highest activity against S. aureus and C. albicans, with remarkable MIC values of 10 μg/mL and 3 μg/mL, respectively. Structure-activity relationship studies were capable to rationalize the effect of different substitutions on the phenyl ring of the azobenzene on antimicrobial activity.
- Concilio, Simona,Sessa, Lucia,Petrone, Anna Maria,Porta, Amalia,Diana, Rosita,Iannelli, Pio,Piotto, Stefano
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- Method for preparing polyimide polymer with azo-pyrimidine structure unit
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The invention relates to a method for preparing a diamine monomer with an azo-pyrimidine structure and a method for preparing a polyimide polymer by adopting the diamine monomer with the azo-pyrimidine structure. The preparation method comprises the following steps: carrying out a coupling reaction on 4-substituted aniline and sodium phenate to obtain 4-hydroxy-4'-substituted azobenzene; and carrying out nucleophilic substitution on the 4-hydroxy-4'-substituted azobenzene and dibromoalkane to generate bromo-azobenzene, and reacting the bromo-azobenzene with 4,6-diamido-2-mercaptopyrimidine to obtain the diamine monomer; and carrying out condensation polymerization on the diamine monomer with dianhydride to obtain polyimide. The pyrimidine structure is introduced into the diamine monomer, so that the charge transfer complex effect of aromatic rings of polyimide is reduced, and the glass transition temperature of the polyimide is reduced; and the azo group has photo-induced anisotropy, and an azo unit is introduced into the polyimide by alkyl chains having different lengths, so that the heterogeneous degree of the azo group can be effectively regulated, and the application of the polyimide in alignment films and other optical fields can be improved to a great extent.
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Paragraph 0080
(2016/10/09)
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- Phthalocyanines with peripheral azo chromophores
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Interaction of 4-halogenated phthalonitrile with arylazophenols provided 4-R-azophenoxyphthalonitriles that have been further transformed into tetra-4-(4′-arylazophenoxy)phthalocyanines and their metal complexes. Physicochemical properties of the prepared
- Tikhomirova,Badaukaite,Shaposhnikov
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p. 2348 - 2353
(2015/11/24)
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- Azobenzene-Based Organic Salts with Ionic Liquid and Liquid Crystalline Properties
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Two sets of new azobenzene-based bromide salts are synthesized, and their thermal photochromic properties are studied. Both sets are based on the imidazolium cation. The first set (1) features a symmetric biscation where two imidazolium head groups (Im) w
- Stappert, Kathrin,Muthmann, Johanna,Spielberg, Eike T.,Mudring, Anja-Verena
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p. 4701 - 4712
(2015/09/15)
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- A convenient protocol for the synthesis of 2-(2′-Hydroxy-5′- carboxyphenyl)-2H-benzotriazole to avoid decarboxylation when using p-hydroxybenzoic acid as coupling component
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In the study of the synthesis of 2-(2′-hydroxy-5′- carboxyphenyl)-2H-benzotriazole, we found that decarboxy intermediate-4-((2- nitrophenyl)diazenyl)phenol was obtained when using p-hydroxybenzoic acid as coupling component. A convenient protocol for the synthesis of 2-(2′-hydroxy-5′-carboxyphenyl)-2H-benzotriazole is reported with methyl-p-hydroxybenzoate as coupling component. Different dizao components and different coupling components were also used for further investigation of decarboxylation.
- Ma, Wei,Tuo, Tingting,Hu, Jingqiang,Liu, Yong,Zhang, Shufen
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p. 803 - 807
(2014/06/10)
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- Synthesis and characterization of new diamines containing side substituted azobenzene groups
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New aromatic diamines containing two side substituted azobenzene groups have been obtained by chemical modification of 2,2-bis(3-amino-4-hydroxyphenyl)-hexafluoropropane with different p-bromoalkyloxy-p'-methyl-azobenzene compounds in the presence of K2CO3/KI. The bromoalkyloxy-methylazobenzenes have been prepared by the reaction of p-hydroxy-p'-methylazobenzene with different dibromoalkanes. All intermediates and the prepared diamines have been characterized by melting points, infrared spectroscopy and proton nuclear magnetic resonance. The new diamines can be used further as monomers for production of new polyimides or copolyimides for high performance applications.
- Sava, Ion,K?pnick, Thomas
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p. 585 - 592
(2015/03/18)
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- New fluorescent symmetrically substituted perylene-3,4,9,10-dianhydride- azohybrid dyes: Synthesis and spectroscopic studies
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Five phenolic azo-dyes (3a-e) were synthesized by diazo coupling of the suitably substituted anilines (1a-e) with phenol at low temperature in alkaline medium. The resulting dyes have low solubility in aqueous medium due to lack of carboxylic or sulfonic
- Saeed, Aamer,Shabir, Ghulam
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- Synthesis and properties of phthalonitriles with an azo chromophore and related phthalocyanines
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The 4-R-phenylazophenoxyphthalonitriles were synthesized by the reaction of 4-bromophthalonitrile with 4-R-phenylazophenols and were used to obtain tetra-R-phenylazophenoxyphthalocyanines and their metal complexes. The effect of substituents on the spectr
- Tikhomirova,Badaukaite,Kulinich,Shaposhnikov
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p. 116 - 123
(2013/04/23)
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- Synthesis and mesomorphic behaviour of achiral four-ring unsymmetrical bent-core liquid crystals: Nematic phases
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Achiral four ring unsymmetrical bent-core liquid crystals derived from 3-amino-2-methylbenzoic acid have been designed and synthesized with an imine, ester and photochromic azo linking moieties. These hockey-stick shape resembling bent molecules possess a
- Paul, Manoj Kumar,Kalita, Gayatri,Laskar, Atiqur Rahman,Debnath, Somen,Gude, Venkatesh,Sarkar, Dipika Debnath,Mohiuddin, Golam,Varshney, Sanjay Kumar,Nandiraju Rao
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- Dinuclear ortho-metallated palladium(II) azobenzene complexes with acetato and chloro bridges: Influence of polar substituents on the mesomorphic properties
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The synthesis, characterization and mesomorphic properties of a new series of acetate and chloro-bridged dinuclear orthopalladated complexes derived from azobenzene with terminal groups of hexadecyloxy moiety at one end and different polar groups (Me, Cl, F, NO2, CN) at the other end are described. The mesomorphic properties of both the ligands and complexes were investigated by polarizing optical microscopy and X-ray studies to understand the effect of polar group in the nature of mesophase produced. Among the complexes, all chloro-bridged complexes predominantly exhibited SmA phase. However the rare phenomenon of observing mesomorphism in acetato-bridged palladium (II) complexes due its typical open book shape had been realized in substituted acetato-bridged complexes with fluoro and cyano substituents in the ligands. Nitro and cyano substituted ligands only exhibited monotropic Smectic A phase. Model molecular arrangement based on X-ray studies is presented.
- Choudhury, Trirup Dutta,Shen, Yongqiang,Rao, Nandiraju V.S.,Clark, Noel A.
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experimental part
p. 20 - 28
(2012/07/14)
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- Solvent-dependent photoresponsive conductivity of azobenzene-appended ionic liquids
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A new class of azobenzene-based photoresponsive ionic liquids was prepared and showed reversible modulation of ionic conductivity in specific solvents under alternative UV/visible light irradiation.
- Zhang, Shiguo,Liu, Shimin,Zhang, Qinghua,Deng, Youquan
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supporting information; experimental part
p. 6641 - 6643
(2011/07/29)
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- Synthesis and photochemical properties of cationic cyclopentadienyliron containing arylazo chromophores
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Two kinds of cationic cyclopentadienyliron complexes containing arylazo chromophores (Azo-Fc) were synthesized through the nucleophilic aromatic substitution reactions of cyclopentadienyliron chlorobenzene complexes. The synthesized Azo-Fc was characterized by LC-MS, IR, and 1H NMR. The influence of substituents and the aryl ring on spectral data of the synthesized compounds is described. Unlike other cationic cyclopentadienyliron complexes, Azo-Fc hardly underwent photolysis and showed no photo-initiating abilities in the cationic polymerization under photo-irradiation; in addition, trans/cis isomerization by irradiation is possible at different wavelengths.
- Li, Guang-Lei,Ye, Hui,Chen, Yu,Zhao, Bao-Dong,Wang, Tao
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scheme or table
p. 1516 - 1519
(2011/10/04)
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- Synthesis of diaryl-azo derivatives as potential antifungal agents
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As compared with a commercially available agricultural fungicide hymexazol, some phenyl-azo phenol derivatives (e.g., 4a, 4b, 4f, 4n, 4q, 4u, and 4v) exhibited the more promising and pronounced antifungal activities in vitro against seven phytopathogenic fungi. It seemed that 4-((un)substituted phenylazo)-phenol and 4-((un)substituted phenylazo)-3-methylphenol might be considered as new lead structures for further design of agricultural fungicides.
- Xu, Hui,Zeng, Xiwen
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supporting information; experimental part
p. 4193 - 4195
(2010/08/22)
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- Dual-controllable stepwise supramolecular interconversions
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A new unsymmetric guest compound comprising ferrocene and azobenzene moieties was synthesized and can form a host-guest system with β-cyclodextrin (β-CD) complexed. The complexation stoichiometries and sites of the ensembles can be selectively controlled
- Zhu, Liangliang,Zhang, Dong,Qu, Dahui,Wang, Qiaochun,Ma, Xiang,Tian, He
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supporting information; experimental part
p. 2587 - 2589
(2010/07/09)
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- Liquid-crystalline polymorphism of symmetrical azobananas: Bis(4-(4-alkylphenyl)azophenyl) 2-nitroisophtalates
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In this paper we present a series of novel compounds, bis(4-(4-alkylphenyl) azophenyl) 2-nitroisophtalates, which exhibit nematic and banana-type liquidcrystalline phases. The alkyl chain length varies from 1 to 18 carbons. The first ten members of this series exhibit nematic phase. The last eleven compounds exhibit banana-type liquid crystalline phases. The propyl and pentyl derivatives have extra second type of banana mesophase. Copyright Taylor & Francis Group, LLC.
- Zygadlo,Dardas,Nowicka,Hofmann,Galewski
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experimental part
p. 283 - 291
(2011/08/02)
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- Novel poly(etherimide)s with attached NLO moieties. I. Synthesis and characterization*
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Two types of novel poly(etherimide)s with attached photoresponsive azobenzene chromophores are presented. The polymers differing in the kind of linkage between the azobenzene units with the polymer chain, i.e. rigid and flexible, and in substituents on th
- Schab-Balcerzak
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experimental part
p. 2293 - 2308
(2009/05/07)
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- Solvatochromic effects in the absorption spectra of some azobenzene compounds
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Solvatochromic behavior of some 4,4′-substituted azoaromatic derivatives has been investigated in solvents of different polarities. The solvent dependent UV/vis spectral shifts, νmax, were analyzed using some physical parameters such as refractive index, dielectric constant, Kamlet-Taft parameters α (hydrogen bond donating ability) and β (hydrogen bond accepting ability). The intermolecular interaction types in the azobenzene derivatives solutions were established on the basis of a multiple linear regression analysis. The fitting coefficients obtained from this analysis allowed us to estimate the contribution of each type of interactions to the total spectral shift in the studied solutions.
- Rusu, Elena,Dorohoi, Dana-Ortansa,Airinei, Anton
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experimental part
p. 216 - 219
(2009/02/06)
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- Liquid crystalline properties of 4-methyl-, 4-ethyl- and 4-propyl-4′-alkyloxyazobenzenes
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Liquid crystalline properties of 4-methyl-4′-alkoxyazobenzenes (azo-1-n), 4-ethyl-4′-alkoxyazobenzenes (azo-2-n) and 4-propyl-4′-alkoxyazobanzenes (azo-3-n) are described. For these three homologous series, temperatures and enthalpies of phase transitions
- Zienkiewicz,Galewski
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p. 359 - 366
(2007/10/03)
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- Mesogenic biphenyl derivatives with azo and ester central linkage
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Biphenyl nucleus comprises one of the most interesting research areas in the study of relations between chemical constitution and mesomorphic properties. Few biphenyl derivatives with azo and ester central linkage having following general formula have been synthesized and their mesomorphic properties were evaluated. Where R=-H, -OCH3, R'=-CH3, -OCH3, -OC2H5, -OC4H9; X=-H, -Br. All the synthesized compounds were characterized by elemental analysis and spectroscopic methods.
- Prajapati
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p. 769 - 777
(2007/10/03)
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- Phase Transitions of Liquid Crystalline Polymethacrylates having 4-(4-Substituted Phenylazo)phenyl Benzoate in a Mesogenic Side Chain
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Two types of liquid crystalline polymethacrylates, having 4-(4-substituted phenylazo)phenyl benzoate in a mesogenic side chain, were prepared.The relationship between the shape of the mesogenic side chain and the liquid crystallinity was studied. - Keywords: liquid crystalline polymethacrylate, nematic, smectic, thermal property, shape of mesogenic side chain
- Ujiie, Seiji,Maekawa, Kazuhiko,Takahashi, Satoshi,Iimura, Kazuyoshi
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p. 477 - 482
(2007/10/02)
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- A Simple Route for the Synthesis of Chlorosubstituted Arylazobenzenes, Arylazonaphtalenes, and Arylazopyrazoles
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The reaction of arylazophenoles and arylazohydroxypyrazoles (or their tautomer hydrazones) 10, 11, and 15 with POCl3 in dimethylformamide yields chlorosubstituted arylazobenzenes or arylazopyrazoles 12, 13 and 16, resp., in moderate to high yields.The substitution of the OH-group by the Cl-moiety is favoured by acceptor substituents in the aryl fragments ortho- and/or para-linked to the azo group.In case that arylazocompounds derived from resorcinol are used the substitution reaction runs in a stepwise manner giving raise to the formation of o-hydroxy-p-chlorosubstit uted azo compounds 18 primarily and then of dichlorosubstituted azo compounds 19.
- Guenther, R.,Jaehne, E.,Hartmann, H.,Schulze, M.
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p. 945 - 954
(2007/10/02)
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- Low excitation energy band of 4-hydroxyazobenzene derivatives
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The low excitation energy band appeared in the electronic spectra of some 4-hydroxyazobenzene derivatives is assigned to an electronic transition of the type η-?*.It is concluded that 4-hydroxyazobenzene derivatives exist mainly in the true azo form.On the other hand, the visible spectra of the azo compound; 4-hydroxy-2-carboxyazobenzene is interpreted on the basis that this compound exists in a tautomeric equilibrium of the type azo hydrazone, originating from the carboxyl group at the ortho position to the azo one.
- Mahmoud, M. R.,Ibrahim, S. A.,Hamed, M. A.
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p. 729 - 734
(2007/10/02)
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- Studies on the Reactivity of Azoxybenzenes. Part 12. αβ-Interconversion of para-Monosubstituted Azoxybenzenes in the Wallach Rearrangement
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Under the reaction conditions for the Wallach rearrangement, 4-methyl-ONN-(1α), 4-methyl-NNO-(1β), 4-nitro-ONN-(2α), and 4-nitro-NNO-azoxybenzene (2β) were found to undergo αβ-interconversion, while 4-bromo-ONN-(3α) and 4-bromo-NNO-azoxybenzene (3β) do not.The αβ-interconversion occurs with both mono- and di-protonated forms of the azoxybenzenes.
- Yamamoto, Jiro,Aimi, Hironori,Masuda, Yasuko,Sumida, Takashi,Umezo, Masahiro,Matuura, Teruo
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p. 1565 - 1568
(2007/10/02)
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- LIQUID CRYSTALS - 8. NEMATOGENIC COMPOUNDS WITH A TERMINAL DIMETHYLAMINOETHOXY GROUP.
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Six p,p prime -disubstituted azo- and azoxybenzenes in which one of the terminal groups is 2-N,N-dimethylaminoethoxy, and their hydrochlorides were synthesized. The three azoxybenzene derivatives exhibit nematic mesomorphism. Neither the azobenzenes nor a
- Alpay,Schroeder,Schroeder
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