- Static Retention of Dynamic Chiral Arrangements for Achiral Shear Thinning Metal–Organic Colloids
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Chiral compounds are known to be important not only because they are the fundamental components of living organisms, but also for their unique chiroptical properties. In recent years, scientists have fabricated several chiral organic supramolecular aggregates by using chiral physical fields, such as vortex flow. Herein, the relationship between dynamic chiroptical properties and rheological nature is discussed, suggesting the shear thinning properties of non-Newtonian fluids might help colloidal particles adopt a chiral arrangement in vortices. Furthermore, the storage modulus of colloids could be increased by adding a linking agent, which successfully kept the dynamic chiroptical properties in the static state. Moreover, the salt effect on the host–guest interaction involved in the colloids was studied, the results suggested a significant enhancement of the transferred dynamic circular dichroism for the achiral guest molecule.
- Huang, Jian-Cai,Xiao, Hui,Chen, Zhixin,Zheng, Wenxu,Huang, Chang-Cang,Wu, Shu-Ting,Xie, Zenghong,Zhuang, Naifeng
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p. 14017 - 14024
(2021/09/02)
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- Colorant with double catechol structure, preparation method and applications thereof
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The invention relates to the technical field of organic colorants, and particularly provides a colorant with a double catechol structure, a preparation method and applications thereof, wherein the colorant has a structural general formula represented by a
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Paragraph 0108; 0113-0114
(2020/05/30)
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- Unraveling the Self-Assembly of Heterocluster Janus Dumbbells into Hybrid Cubosomes with Internal Double-Diamond Structure
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Cubosomes are bicontinuous cubic-phase particles generated by amphiphile self-assembly with bicontinuous cubic phases, which creates an intricate network of interconnected nanochannels that endow these materials with special functions for advanced applications. On the other hand, clusters are an attractive class of molecules that exhibit intriguing functions and properties that differ from those of atoms and nanoparticles. Inspired by lipid self-assembly and attracted to the new functionalities of clusters, we prepared special heterocluster Janus dumbbells (HCJDs) composed of dissimilar nanoclusters: namely, a polyoxometalate and a polyhedral oligomeric silsesquioxane. HCJDs resemble conventional amphiphiles and, as such, they self-assemble in solution into faceted hybrid cubosomes via the transformation of vesicles into spongelike aggregates. Multiple mechanisms that lead to equilibrium, including molecular self-assembly, vesicle accumulation, membrane fusion, inner-structure reorganization, and cubic crystal growth, contributed to the overall process. On the basis of these results, we proposed a strategy for self-assembly - from basic molecular design that goes beyond traditional amphiphiles to the construction of micro- or nanomaterials with hierarchical structures and advanced functions.
- Liu, Hong-Kai,Ren, Li-Jun,Wu, Han,Ma, Yong-Li,Richter, Sven,Godehardt, Michael,Kübel, Christian,Wang, Wei
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supporting information
p. 831 - 839
(2019/01/23)
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- Synthesis and characterization of ferrocenyl esters: Their anti-oxidant activity and DNA-binding ability
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In continuation to our work on biologically active material, some new ferrocenyl esters were prepared by condensation of 4-ferrocenyl phenol (ROH) with ferrocenyl dicarboxylic acid chlorides (DCC) at low temperature. The synthesized compounds (E1-E9) were characterized by analyzing their physical properties, FT-IR, 1H-NMR, UV-visible spectroscopic and cyclic voltammetric studies. The DPPH free radical scavenging assay was performed to explore their potential as antioxidant which showed that the E1 had maximum scavenging ability (77.11%) whereas E3 showed minimum (52%) compared with the standard. Cyclic voltammetric studies indicated that these compounds were electroactive in potential window of 2.0-0.0V. Binding mode found in these esters was an electrostatic interaction which is considered as strongest amongst all. Therefore, these compounds are considered to have DNA-binding capability and are potential DNA binders.
- Bukhari, Syeda Anam,Gul, Asghari,Akhter, Zareen,Bashir, Amna
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p. 375 - 382
(2018/06/06)
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- Multistate Photoswitches: Macrocyclic Dihydroazulene/Azobenzene Conjugates
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Molecules comprised of three covalently linked bi-stable switches can exist in states described by a combination of binary numbers, one for each individual switch: ?000?, ?001?, etc. Here we have linked three photo-/thermoswitches together in a rigid macrocyclic structure, one azobenzene (bit no 1) and two dihydroazulenes (DHAs; bits no 2 and 3) and demonstrate how electronic interactions and unfavorable strain in some states can be used to control the speed by which a certain state is reached. More specifically, upon irradiation of state ?000?, the AZB isomerizes from trans to cis and the two DHAs to vinylheptafulvenes (VHFs), generating ?111?. The thermal VHF-to-DHA back-reactions from this state also occur stepwise and can be accelerated by photo-induced AZB cis-to-trans conversion, proceeding via ?011? to ultimately furnish ?000?. Overall, the accessibility to a specific state of one bit was found to depend on the states of its neighboring bits.
- Vlasceanu, Alexandru,Koerstz, Mads,Skov, Anders B.,Mikkelsen, Kurt V.,Nielsen, Mogens Br?ndsted
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supporting information
p. 6069 - 6072
(2018/04/30)
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- Synthesis and self-assembly of photoresponsive and luminescent polycatenar liquid crystals incorporating an azobenzene unit interconnecting two 1,3,4-thiadiazoles
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Novel polycatenar liquid crystals containing two 1,3,4-thiadiazole rings interconnected by an azobenzene central linkage have been synthesized and investigated by polarizing microscopy, DSC, X-ray scattering, SEM, UV-vis spectroscopy and photoluminescence measurements. These compounds can self-assemble into SmC, Colhex/p6mm and CubI/Pm3n liquid crystalline phases in the bulk states and form multistimuli responsive organogels in organic solvents. They have reversible photoresponsive properties in solution, liquid crystalline states and gel states. They also show fluorescence emission with large Stokes shift in solution and binding selectivity to Cu2+ among a series of cations in CH3CN-CH2Cl2 solution.
- Peng, Xiongwei,Gao, Hongfei,Xiao, Yulong,Cheng, Huifang,Huang, Fanran,Cheng, Xiaohong
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supporting information
p. 2004 - 2012
(2017/03/10)
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- Hypoxia-responsive drug–drug conjugated nanoparticles for breast cancer synergistic therapy
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In order to eliminate tumors, it is necessary to kill differentiated cancer cells, cancer stem cells (CSCs) and the “vascular niche” synergistically. Although nanoparticles (NPs) have been used to deliver drugs to the action sites, inert materials with high toxicity may reduce the drug loading content and cause side-effects to kidneys and other organs in the course of degradation and excretion. Here, we report hypoxia-responsive drug–drug conjugated NPs to deliver three drugs to kill differentiated cancer cells, CSCs and the “vascular niche” synergistically, which could selectively release the drugs to treat cells in hypoxic tumors. For this purpose, an azobenzene (AZO) bond imparting hypoxia sensitivity and specificity as a crosslinker conjugated hydrophobic combretastatin A-4 (CA4) with hydrophilic irinotecan (IR) to form IR–AZO–CA4 amphiphilic molecules. These molecules self-assembled into NPs, which could encapsulate hydrophobic anti-CSCs drug cyclopamine (CP). The drug–drug conjugated NPs had high drug loading content. As expected, the AZO linker could be broken under hypoxia conditions and the NPs were disassembled to release drugs quickly. Confocal laser scanning microscopy (CLSM) results indicated that the IR–AZO–CA4/CP NPs could enhance the cellular uptake of drugs and the permeability of drugs to the inner of CSCs, beneficial for tumor therapy. Furthermore, the IR–AZO–CA4/CP NPs could inhibit the migration, invasion and mammosphere formation capacity of CSCs. More importantly, only IR–AZO–CA4/CP NPs could simultaneously inhibit differentiated cancer cells, CSCs and endothelial cells without interference on the cell under a normoxic environment. The present study suggests that the IR–AZO–CA4/CP NPs provide a promising therapeutic approach for anticancer treatment.
- Zhang, Ruilong,Li, Yan,Zhang, Miao,Tang, Qunwei,Zhang, Xin
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p. 30268 - 30276
(2019/01/14)
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- Novel Carbazole (Cbz)-Based Carboxylated Functional Monomers: Design, Synthesis, and Characterization
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A series of novel functional carbazole (Cbz)-based carboxylated monomers were synthesized and characterized. A Clauson-Kaas procedure, a deprotection step, amide coupling, and hydrolysis were utilized as key chemical reactions towards the multistep synthesis of monomers in good to excellent isolated yields. The design strategy was further extended to complex carbazole-COOH monomers incorporated arylazo groups as photoreactive moieties. In addition, photoreactive hybrid carbazole (Cbz)-pyrrole (Pyr)-based carboxylated monomers, comprising a pyrrole core linking a carbazole and a photoreactive phenylazide or benzophenone moiety through an amide spacer in the molecular structure, were also synthesized. The latter can be utilized for surface modification of polymeric films in their monomeric form or as polymeric microparticles (MPs). Functional monomers: Novel functional carbazole-based carboxylated monomers were accessed using a Clauson-Kaas procedure, a deprotection step, amide coupling, and hydrolysis in a multistep synthesis. The design strategy was extended to complex carbazole-COOH monomers incorporating arylazo and phenylazide or benzophenone as photoreactive moieties, which can be utilized for functionalization/decoration of various polymeric and non-polymeric surfaces, matrices, and non-functional nanomaterials in their monomeric states or as polymeric microparticles (MPs).
- Mondal, Ejabul,Lellouche, Jean-Paul,Naddaka, Maria
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p. 489 - 496
(2015/10/05)
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- Development of hypoxia-triggered prodrug micelles as doxorubicin carriers for tumor therapy
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Hypoxia has a major role in tumor development and resistance to therapy. Therefore, the effective targeting and killing of hypoxic tumor cells is a key to successful tumor control. Here, we report the hypoxia-responsive prodrug micelles to deliver hydrophobic anticancer drug, which can selectively release the drugs to treat hypoxic tumor cells in a combined way. For this purpose, an azobenzene (AZO) bond, which imparts hypoxia sensitivity and specificity as cross linker, conjugated PEG-hexanethiol (PEG-C6) with combretastatin A-4 (CA4) to form PEG-C6-AZO-CA4 amphiphilic molecule. These PEG-C6-AZO-CA4 molecules self-assemble into micelles, which can encapsulate hydrophobic anticancer drug. The drug release behavior from PEG-C6-AZO-CA4 micelles was studied under normoxic or hypoxic conditions and the combinations of CA4 with hydrophobic drugs for tumor treatment in vitro were also investigated. As the first example of using AZO linkages to develop anticancer prodrug micelles as hydrophobic anticancer drugs delivery to kill the hypoxic tumor cells in a combination way, this study establishes PEG-C6-AZO-CA4 micelles as a promising drug delivery platform for hypoxic tumor therapy. This journal is
- Liu, Hongmei,Zhang, Ruilong,Niu, Yunwei,Li, Yan,Qiao, Chenmeng,Weng, Jie,Li, Jun,Zhang, Xiaoning,Xiao, Zuobing,Zhang, Xin
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p. 20848 - 20857
(2015/03/18)
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- Synthesis, crystal structure and Cu2+ recognition of novel azobenzene derivatives
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Three novel azobenzene derivatives have been synthesised from (E)-4,4′-bischloroformyl azobenzene and arylamines. The crystal structure of (E)-[{diazene-1,2-diylbis(4,1-phenylene)}bis{(3,5-dimethyl-1H-pyrazol-1-yl) methanone}] has been obtained The UV-Vis
- Wang, Wei,Li, Mingzhu,Yu, Xiaolong,Zhang, Qiang,Jiang, Xiaoyu,Wang, Junwu,Gao, Yan
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- Synthesis and characterization of novel electrochromic and photoresponsive materials based on azobenzene-4,4′-dicarboxylic acid dialkyl ester
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Novel electrochromic and photoresponsive materials based on azobenzene-4,4′-dicarboxylic acid dialkyl ester derivatives (ADDEDs) were successfully prepared and characterized through nuclear magnetic resonance spectroscopy, Fourier transform infrared spectroscopy, and high-performance liquid chromatography-mass spectrometry. The electrochromic behavior, electrochromic mechanism, electro-optical properties, and photoresponsive properties of ADDEDs were investigated through cyclic voltammetry and ultraviolet-visible absorption spectra. ADDEDs displayed not only outstanding electrochromic behavior but also good and reversible photoisomerization properties even under electrochromic conditions. Electrochromic devices (ECDs) based on ADDEDs were fabricated, and their electrochromic performance was analyzed. The ECDs presented a color change from colorless to magenta between 0.0 V (bleached state) and ±3.0 V (colored state). In addition, the ECDs exhibited fast switching times, reasonable contrast, satisfactory optical memories, and redox stability. The novel redox-active azobenzene derivatives are promising candidates for full-color EC display devices, electronic paper, smart windows, optical memory devices, dual-stimuli-responsive systems, as well as other potential new applications. This journal is
- He, Li-Hua,Wang, Guo-Ming,Tang, Qian,Fu, Xiang-Kai,Gong, Cheng-Bin
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p. 8162 - 8169
(2015/05/20)
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- Liquid-crystal aromatic polyesters containing azo and sulfone units
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Two novel aromatic polyesters containing azo and sulfone units were synthesized by poly-condensation of 4,4′-azobenzene-dicarbonyl chloride with dihydroxydiphenyl sulfones at low temperature. The synthesized polymers exhibited good solubility, inherent viscosity (reaches 1.05 dL g-1), high glass transition temperature (above 200 °C) and thermal stability (≤ 5 % weight loss at 348 °C), which were characterized by Fourier transform infrared spectroscopy. The liquid crystalline and photoisomerization properties were observed by polarizing optical microscope and an ultraviolet-visible spectrophotometer.
- Qiu, Ming Yan,Niu, Yong Sheng,Yu, You Zhu,Guo, Yu Hua
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p. 7759 - 7762
(2015/02/02)
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- Synthesis and mercury ion recognition of a novel azobenzene derivative bearing naphthalene units
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A fluorescent probe for selective detection of mercury based on an azobenzene derivative bearing naphthalene units has been synthesised and its cation recognition abilities examined by UV-Vis and fluorescence spectroscopy. The fluorescent probe exhibits a
- Wanga, Wei,Jiang, Xiaoyu,Zhang, Qiang,Li, Mingzhu,Yu, Xiaolong,Wang, Junwu,Gaob, Yan
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p. 662 - 664
(2014/01/17)
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- ENCAPSULATES
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The present application relates to encapsulates, compositions, products comprising such encapsulates, and processes for making and using such encapsulates. Such encapsulates comprise a core comprising a perfume and a shell that encapsulates said core, such encapsulates may optionally comprise a parametric balancing agent, such shell comprising one or more azobenzene moieties.
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Page/Page column 61
(2013/03/26)
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- Synthesis and characterization of azo aromatic diacyl chlorides
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A convenient and rapid method for the synthesis of azo aromatic diacyl chlorides has been developed. Eight azo aromatic diacyl chlorides have been synthesized from aromatic nitro acids by using xylene as solvent. Most reaction periods are less than 2 h and the products are obtained in excellent yields with high purity.
- Qiu, Ming Yan,Zhang, Ji Chang,Shi, Wei Yun,Jia, Qing Chao,Niu, Yong Sheng
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experimental part
p. 2295 - 2297
(2012/09/22)
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- Synthesis and antipestal studies of a novel heterocyclic multidentate schiff base and its transition metal complexes
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A new heterocyclic multidentate Schiff base ligand bis[2-(6-methylpyridin- 2-ylimino)phenyl]-4,4'-(diazene-1,2-diyl)dibenzoate (BMDD, L) and its metal chelates with some transition metal ions viz., Co(II), Ni(II), Cu(II) and Zn(II) have been synthesized a
- Kumar, Hemant,Chaudhary, Ram Pal
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scheme or table
p. 3025 - 3028
(2012/02/02)
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- Novel compounds for the prophylaxis and treatment of inflammatory bowel diseases
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Novel compounds are disclosed for the prophylaxis and treatment of inflammatory bowel disease (IBD) via the administration of an effective amount in a suitable pharmaceutical dosage of agents that are active by themselves or can deliver tin the large intestine active forms of the drugs such as 5ASA or benzoxazole acetic acid or platelet activating factors. The mechanism of the release is based on bacterial cleavage of an azo linkage in the mammalian lower bowel to release the active compound(s).
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Page/Page column 5
(2010/11/25)
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- Photocontrolled folding and unfolding of a collagen triple helix
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(Figure Presented) At the flick of a switch: Two side chains of a collagen peptide containing (2S,4S)-mercaptoproline at two defined positions are linked with a diiodo azobenzene derivative. With the trans isomer of the azobenzene clamp (orange), the pept
- Kusebauch, Ulrike,Cadamuro, Sergio A.,Musiol, Hans-Juergen,Lenz, Martin O.,Wachtveitl, Josef,Moroder, Luis,Renner, Christian
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p. 7015 - 7018
(2007/10/03)
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- Benzoxazole derivatives for the prophylaxis and treatment of inflammatory bowel diseases
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The present invention relates to novel compounds for the prophylaxis and treatment of inflammatory bowel disease (IBD) via the administration of an effective amount in a suitable pharmaceutical dosage of agents that are active by themselves or can deliver tin the large intestine active forms of the drugs such as 5ASA or benzoxazole acetic acid or platelet activating factors. The mechanism of the release is based on bacterial cleavage of an azo linkage in the mammalian lower bowel to release the active compound(s).
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Page/Page column 8; 10
(2010/11/23)
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- Synthesis and photoresponsive study of azobenzene centered polyamidoamine dendrimers
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A new series of novel polyamidoamine (PAMAM) dendrimers 4, 5 and 6 possessing azobenzene units specifically at the core were prepared and their reversible trans/cis photoisomerization properties were studied. PAMAM dendritic wedges as well as azo-based PAMAM dendrimers were fully characterized by means of FT-IR, NMR (1H and 13C), mass spectrometry (MALDI-MS), thermogravimetric and elemental analysis.
- Ghosh, Samaresh,Banthia, Ajit K.,Chen, Zhu
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p. 2889 - 2896
(2007/10/03)
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- Sol-gel phase transition induced by fiber-vesicle structural changes in sugar-based bolaamphiphiles
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The research objects of this paper were to design bolaamphiphilic gelators utilizing a sugar family as a source of solvophilic groups and an azobenzene segment as a solvophobic group and to monitor the aggregation mode utilizing the spectroscopic properti
- Kobayashi, Hideki,Koumoto, Kazuya,Jung, Jong Hwa,Shinkai, Seiji
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p. 1930 - 1936
(2007/10/03)
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- Synthesis of photoresponsive polyamidoamine (PAMAM) dendritic architecture
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Polyamidoamine (PAMAM) dendrimer 1 with an azobenzene central linker has been synthesized and found to undergo reversible trans/cis isomerization upon exposure to UV-light.
- Ghosh, Samaresh,Banthia, Ajit K.
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p. 501 - 503
(2007/10/03)
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- Characterization of simple photoresponsive systems and their applications to metal ion transport
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Some new photoresponsive azobenzenes (1-5) have been synthesized and characterized.On irradiation at 330 nm these systems undergo conversion from the E to the Z form to a varying extent which depends upon the nature and position of substitution on the azobenzene rings.They revert back to the E form on thermal isomerization in the dark.Photochemical equilibria have been studied and compared in acetonitrile and o-dichlorobenzene; E forms are stabilized more in o-dichlorobenzene than in acetonitrile.Two of the molecules (1 and 4) show enhanced transport of Cu2+ ions across a liquid membrane on irradiation.
- Ameerunisha, Sardar,Zacharias, Panthappally S.
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p. 1679 - 1682
(2007/10/02)
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- Isomeric Double Decker Porphyrins Bridged by Four Azobenzene Units
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A novel macropentacyclic system (1) containing double layered porphyrin units which are bridged by four azobenzene links has been synthesized, two stable isomers being isolated, differing in spatial arrangement of the amide groups and azobenzene links; the complex formation of these compounds with zinc(II) is reported.
- Neumann, Karl Heinz,Voegtle, Fritz
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p. 520 - 522
(2007/10/02)
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- Competitive Singlet-Singlet Energy Transfer and Electron Transfer Activation of Aryl Azides: Application to Photo-Cross-Linking Experiments
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Direct irradiation of 4-phenyl azide (DAA) in an inert solvent with UV light causes ring expansion to an inermediate dehydroazepine and eventual isolation of 4,4'-azobisbenzene> (AZB).The dehydroazepine can be trapped with nucleophilic reagents to give substituted 3H-azepines.The photochemistry of DAA takes a different course when it is sensitized by pyrene, 1-acetamidopyrene (5), or 9-acetamidoacridine (2).Under these conditions, single-electron transfer occurs in competition with energy transfer as evidenced by detection of radical ions in laser transient absorption spectroscopy and by formation of 4-aniline (DAH) as a major product.Energy transfer and electron transfer compete also when the sensitizer and the aryl azide are linked together by a flexible chain of methylene groups.These results have particular significance for the application of such compounds to phtolabeling experiments.
- Shields, Charles J.,Falvey, Daniel E.,Schuster, Gary B.,Buchardt, Ole,Nielsen, Peter E.
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p. 3501 - 3507
(2007/10/02)
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- BILAYER COATED CAPSULE MEMBRANES. PART 2. PHOTORESPONSIVE PERMEABILITY CONTROL OF SODIUM CHLORIDE ACROSS A CAPSULE MEMBRANE
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Two types of photoresponsive nylon capsules coated with synthetic bilayer membranes were prepared.In one system, the azobenzene chromophore is incorporated in the bilayer component (System I); the other system contains the azobenzene moiety as part of the polyamide chain (System II).Release of NaCl from nylon capsules coated with photoresponsive bilayer membranes (System I) was reversibly regulated by alternate irradiation with u.v. or visible light.Thus, permeation of NaCl was enhanced due to the distored cis-configuration ot the azobenzene unit in bilayers, and reverted to the original rate by recovery of the trans-configuration.NaCl release was also affected by the phase transition of the coating bilayer membrane.The permeation mechanism is discussed from the activation energy data.Permeation of the System II capsule, in which the azobenzene unit is linked covalently, was not changed by photoirradiation.
- Okahata, Yoshio,Lim, Han-jin,Hachiya, Satoshi
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p. 989 - 994
(2007/10/02)
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