- Nonlinear optical properties of diaromatic stilbene, butadiene and thiophene derivatives
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Series of highly polar stilbene (1a-e), diphenylbutadiene (2a-c) and phenylethenylthiophene (3a-c) derivatives were preparedviaHorner-Wadsworth-Emmons method with a view to produce new and efficient materials for second harmonic generation (SHG) in the so
- Kukkonen, Esa,Lahtinen, Elmeri,Myllyperki?, Pasi,Haukka, Matti,Konu, Jari
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p. 6640 - 6650
(2021/04/22)
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- Charge neutral rhenium tricarbonyl complexes of tridentate N-heterocyclic carbene ligands that bind to amyloid plaques of Alzheimer's disease
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Two tridentate ligand systems bearing N-heterocyclic carbene (NHC), amine and carboxylate donor groups coupled to benzothiazole- or stilbene-based amyloid binding moieties were synthesised. Reaction of the imidazolium salt containing pro-ligands with Re(CO)5Cl yielded the corresponding rhenium metal complexes which were characterised by NMR, and X-ray crystallography. These ligands are of interest for the potential preparation of technetium-99m imaging agents for Alzheimer's disease and the capacity of these rhenium complexes bind to amyloid fibrils composed of amyloid-β peptide and amyloid plaques in human frontal cortex brain tissue was evaluated using fluorescence microscopy. These studies show that the complexes bound efficiently to amyloid-β fibrils and some evidence of binding to amyloid-β plaques.
- Barnard, Peter J.,Donnelly, Paul S.,McLean, Catriona A.,Noor, Asif,Wiratpruk, Nuchareenat
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supporting information
p. 4559 - 4569
(2020/04/17)
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- Copper Bis(thiosemicarbazonato)-stilbenyl Complexes That Bind to Amyloid-β Plaques
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Alzheimer's disease is characterized by the presence of extracellular amyloid-β plaques. Positron emission tomography (PET) imaging with tracers radiolabeled with positron-emitting radionuclides that bind to amyloid-β plaques can assist in the diagnosis o
- Cullinane, Carleen,Donnelly, Paul S.,Hayne, David J.,Lim, SinChun,McLean, Catriona A.,Noor, Asif,Roselt, Peter D.,Van Zuylekom, Jessica K.,White, Jonathan M.
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p. 11658 - 11669
(2020/08/24)
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- Molecular probes for imaging of myelin
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A molecular probe for labeling myelin includes a fluorescent trans-stilbene derivative.
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Page/Page column 23; 28-30
(2018/06/18)
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- Theoretical and Experimental Studies of N,N-Dimethyl-N′-Picryl-4,4′-Stilbenediamine
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N,N-dimethyl-N′-picryl-4,4′-stilbenediamine (DMPSDA) was prepared, purified and crystallised in a form of black lustrous crystals, and its absorption and fluorescence spectra were recorded in cyclohexane, acetonitrile and dimethyl sulfoxide. Non-emissive
- Papper, Vladislav,Wu, Yuanyuan,Kharlanov, Vladimir,Sukharaharja, Ayrine,Steele, Terry W. J.,Marks, Robert S.
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- New organic conjugated dye nano-aggregates exhibiting naked-eye fluorescence color switching
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In this study, a variety of new conjugated containing strong electron-donating groups were prepared for formation of organic nano-scale aggregates. The properties and aggregation modes of these aggregates were investigated on basis of time dependent absorption, fluorescence emission spectra as well as scanning electron microscope images. The results show that nano organic aggregates could be yielded by the linear dyes in mixed DMF/H2O solvent through a simple re-precipitation method, while no aggregates of the branched dyes were produced. X-ray diffraction of single crystal and X-ray diffraction patterns of the powders results demonstrate that the linear dyes tend to show ordered molecular arrangements, while the armed dyes do not exhibit such a tendency. A remarkable fluorescence switching process under 365 nm lamp was observed for the target aggregates. This study successfully provides real examples of organic aggregates in mixed DMF/H2O solvent which have great capacity to show enhanced fluorescence color switching.
- Ding, Ge,Lu, Yao,Qin, Xiaozhuan,Su, Jihong,Zhang, Shengtao,Li, Hongru,Luo, Ziping,Chen, Lingyun,Gao, Fang
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- Rhenium(i) complexes of N-heterocyclic carbene ligands that bind to amyloid plaques of Alzheimer's disease
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A series of [Re(i)L(CO)3]+ complexes (where L is a bifunctional bis(NHC)-amine ligand) that are analogues of potential Tc-99m diagnostic imaging agents for Alzheimer's disease have been synthesised. One of the complexes bound to amyl
- Chan, Chung Ying,Noor, Asif,McLean, Catriona A.,Donnelly, Paul S.,Barnard, Peter J.
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supporting information
p. 2311 - 2314
(2017/02/23)
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- Fluorescent gelators for detection of explosives
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Carbazole-, quinoline-, benzothiazole-, and stilbene-containing fluorescent gelators are synthesized by connecting gelationdriving segments, and their gelation abilities are studied with 13 solvents. Fibrous thin-layer films are prepared on quartz plates
- Hanabusa, Kenji,Takata, Shingo,Fujisaki, Masafumi,Nomura, Yasushi,Suzuki, Masahiro
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p. 1391 - 1401
(2017/08/02)
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- Evaluating two new Schiff bases synthesized on the inhibition of corrosion of copper in NaCl solutions
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Two kinds of new Schiff base derivatives, 2-((4-(4-(dimethylamino)styryl)phenylimino)methyl) (DSM) and its intermediate 4-(4-aminostyryl)-N,N-dimethylaniline (AND), form self-assembled monolayers (SAMs) on copper surfaces. The SAMs have been examined by a series of techniques, including contact angle (CA), atomic force microscope (AFM), scanning electronic microscope (SEM), and electrochemical measurements. The results suggest that the two derivatives adsorb onto the copper surface and generate corresponding hydrophobic films, which play an important role in the anticorrosion of copper in 3% NaCl solution. Quantum chemical calculations and molecular dynamics (MD) simulation are also used for further insight into the adsorption mechanism.
- Zhou, Yang,Xu, Shenying,Guo, Lei,Zhang, Shengtao,Lu, Hao,Gong, Yulong,Gao, Fang
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p. 14804 - 14813
(2015/03/05)
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- Solvatochromic behavior of dyes with dimethylamino electron-donor and nitro electron-acceptor groups in their molecular structure
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Six dyes with N,N-dimethylaminophenyl and 4-nitrophenyl or 2,4-dinitrophenyl groups in their molecular structures were prepared and characterized. These compounds have different conjugated bridges (C-C, C-N, and N-N) connecting the electron-donor and the electron-acceptor groups. All compounds are solvatochromic, with reverse solvatochromism occurring. The solvatochromic band observed in each spectrum for the dyes is due to a π rarr π? transition, of an intramolecular charge transfer nature, which occurs from the electron-donor N,N-dimethylaminophenyl group to the electron-acceptor group in the molecules, which is reinforced by the structures of the compounds optimized by applying density functional theory, which exhibit high planarity. The reverse solvatochromism was explained considering two resonance structures. The benzenoid form is better stabilized in less polar solvents and characterizes the region displaying positive solvatochromism, while the dipolar form is better stabilized in more polar solvents, in the region of negative solvatochromism. The Catalán multiparametric approach was used to study the contribution of solvent acidity, basicity, dipolarity, and polarizability to the solvatochromism exhibited by the compounds. These compounds are good candidates for the investigation of the polarizability and, to a lesser extent, the dipolarity of the medium, with very little interference from specific interactions of the solvent through hydrogen bonding.
- De Melo, Carlos E. A.,Nandi, Leandro G.,Domínguez, Moisés,Rezende, Marcos C.,Machado, Vanderlei G.
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p. 250 - 260
(2015/03/31)
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- Novel photochrome aptamer switch assay (PHASA) for adaptive binding to aptamers
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A novel Photochrome-Aptamer Switch Assay (PHASA) for the detection and quantification of small environmentally important molecules such as toxins, explosives, drugs and pollutants, which are difficult to detect using antibodies-based assays with high sensitivity and specificity, has been developed. The assay is based on the conjugation of a particular stilbene-analyte derivative to any aptamer of interest. A unique feature of the stilbene molecule is its reporting power via trans-cis photoisomerisation (from fluorescent trans-isomer to non-fluorescent cis-isomer) upon irradiation with the excitation light. The resulting fluorescence decay rate for the trans-isomer of the stilbene-analyte depends on viscosity and spatial freedom to rotate in the surrounding medium and can be used to indicate the presence of the analyte. Quantification of the assay is achieved by calibration of the fluorescence decay rate for the amount of the tested analyte. Two different formats of PHASA have been recently developed: direct conjugation and adaptive binding. New stilbene-maleimide derivatives used in the adaptive binding format have been prepared and characterised. They demonstrate effective binding to the model thiol compound and to the thiolated Malachite Green aptamer.
- Papper, Vladislav,Pokholenko, Oleksandr,Wu, Yuanyuan,Zhou, Yubin,Jianfeng, Ping,Steele, Terry W. J.,Marks, Robert S.
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p. 1581 - 1591
(2015/02/19)
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- Design, synthesis, and evaluation of multitarget-directed resveratrol derivatives for the treatment of Alzheimer's disease
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A series of multitarget-directed resveratrol derivatives was designed and synthesized for the treatment of Alzheimer's disease (AD). In vitro studies indicated that most of the target compounds exhibit significant inhibition of self-induced β-amyloid (Aβ)
- Lu, Chuanjun,Guo, Yueyan,Yan, Jun,Luo, Zonghua,Luo, Hai-Bin,Yan, Ming,Huang, Ling,Li, Xingshu
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p. 5843 - 5859
(2013/08/23)
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- Substituent effects on the 13C NMR chemical shifts of the imine carbon in N-(4-X-benzylidene)-4-(4-Y-styryl) anilines
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Long-range electronic substituent effects were targeted using the substituent dependence of δC(C=N), and specific cross-interactions were explored extendedly. A wide set of N-(4-X-benzylidene)- 4-(4-Y-styryl) anilines, p-X-C6H4
- Fang, Zhengjun,Cao, Chenzhong,Chen, Guanfan
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p. 1343 - 1350
(2013/08/24)
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- MOLECULAR PROBES FOR IMAGING OF MYELIN
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A molecular probe for labeling myelin includes a fluorescent trans-stilbene derivative.
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- Excited state intramolecular proton transfer of new diphenylethylene derivatives bearing imino group: A combination of experimental and theoretical investigation
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In this paper, we described the synthesis and characterization of new diphenylethylene bearing imino group. We concentrated particularly on the investigation of the possibility of the excited state intramolecular charge transfer (ESIPT) of the new dyes ex
- Gao, Fang,Zhong, Xiaolin,Wang, Qi,Li, Hongru,Zhang, Shengtao
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experimental part
p. 1057 - 1068
(2010/11/17)
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- A highly stereoselective synthesis of stilbenes under solvent-free conditions
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A highly stereoselective synthesis of stilbenes (trans-1,2-diarylethylenes) was achieved under solvent-free conditions from aryl-aldehydes and aromatic substances bearing an activated methyl group in the presence of anhydrous K 2CO3 and poly(ethylene glycol). This method avoided the need for completely anhydrous condition and use of a noxious organic solvent.
- Li, Xia-Bing,Wang, Li,Zhang, Xi-Quan,Gu, Hong-Mei,Guo, Jian,Li, Bao-Lin
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experimental part
p. 489 - 492
(2011/01/05)
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- Molecular probes for imaging myelinated white matter in CNS
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Abnormalities and changes in myelination in the brain are seen in many neurodegenerative disorders such as multiple sclerosis (MS). Direct detection and quantification of myelin content in vivo is desired to facilitate diagnosis and therapeutic treatments of myelin-related diseases. The imaging studies require use of myelin-imaging agents that readily enter the brain and selectively bind to myelinated regions. For this purpose, we have systematically evaluated a series of stilbene derivatives as myelin imaging agents. Spectrophotometry-based and radioligand-based binding assays showed that these stilbene derivatives exhibited relatively high myelin-binding affinities. In vitro myelin staining exhibited that the compounds selectively stained intact myelinated regions in wild type mouse brain. In situ tissue staining demonstrated that the compounds readily entered the mouse brain and selectively labeled myelinated white matter regions. These studies suggested that these stilbene derivatives can be used as myelin-imaging probes to monitor myelin pathology in vivo.
- Wu, Chunying,Wei, Jinjun,Tian, Donghua,Feng, Yue,Miller, Robert H.,Wang, Yanming
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experimental part
p. 6682 - 6688
(2009/11/30)
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- A joint theoretical and experimental insight into the electronic structure of chromophores derived from 6H,12H-5,11-methano-dibenzo[b,f][1,5]diazocine
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We report on the synthesis and electronic spectra of the chiral, donor-acceptor (push-pull) chromophores (±)-4 and (±)-5 with a 6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine scaffold (Scheme 1 and Fig. 2). The electronic structures of these compounds were investigated at a quantum-chemical level (Figs. 2 and 3). The chemical reactivity of 6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine ((±)-11) towards aromatic electrophilic substitution (Scheme 2 and Table) provided additional information about its electronic structure and confirmed nonnegligible derealization of the lone pair of the bridge-head N-atoms in this heterocyclic system.
- Lemaur, Vincent,Cornil, Jerome,Didier, Delphine,Mujawase, Aline,Sergeyev, Sergey
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p. 2087 - 2095
(2008/03/18)
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- Spectroscopic Correlations between Supermolecules and Molecules. Anatomy of the Ion-Modulated Electronic Properties of the Nitrogen Donor in Monoazacrown-Derived Intrinsic Fluoroionophores
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The synthesis, absorption and emission spectra, fluorescence quantum yields, and fluorescence lifetimes of three compound series of trans-4,4′-disubstituted aminostilbenes (1-3) are reported. The chromo-/fluoroionophoric behavior of the monoaza-15-crown-5
- Yang, Jye-Shane,Hwang, Chung-Yu,Hsieh, Chia-Chun,Chiou, Shih-Yi
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p. 719 - 726
(2007/10/03)
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- Photochemical reactions of nitroso oxides at low temperatures: The first experimental evidence for dioxaziridines
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Several singlet nitroso oxides (3a - e) were generated by the thermal reaction of triplet nitrenes (2a - e) with triplet oxygen at 95 K in 2-methyltetrahydrofuran. After photolysis of the nitroso oxides at 77 K using strong light intensities, the formation of intermediates was observed for the first time. From spectroscopic, kinetic, and chemical arguments, we postulate the formation of the following dioxaziridines: 4-(dioxaziridinyl)stilbene (4a), 4-(dioxaziridin-yl)-4′-nitrostilbene (4b), 4′-(dioxaziridin-yl)-4-(dimethylamino)stilbene (4c), 4′-(dioxaziridin-yl)-4-aminobiphenyl (4d), and 4-(dioxaziridin-yl)-4′-(nitrene-substituted)stilbene (4f). All dioxaziridines observed are highly reactive species. At 77 K, they react thermally to form the corresponding nitro compounds (5). The velocity of the ring opening reaction of the dioxaziridines (4 → 5) is not significantly influenced by substituents; the rate constants at 77 K are all equal to 0.0030 ± 0.0005 s-1. The transients were characterized by stationary UV/vis and/or ESR spectroscopy. Ab initio calculations of the thermal reaction of the nonsubstituted dioxaziridine (6) and N-phenyldioxaziridine (9) were performed. From this, it follows that dioxaziridines are experimentally observable species which are separated from the corresponding nitro products by an orbital symmetry-forbidden barrier.
- Harder,Wessig,Bendig,Stoesser
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p. 6580 - 6588
(2007/10/03)
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- Direct CC Triple Bond Formation from the C=C Double Bond and Direct Hydroxylation into the o-Position of a Nitro Group on the Benzene Nucleus with Potassium t-Butoxide in N,N-DImethylformamide in the Air
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A novel and facile method for direct CC acetylenic bond formation from the C=C double bond by treatment with potassium t-butoxide (t-BuOK) in N,N-dimethylformamide in the air has been found in a 9,10-bis(4-substituted styryl)anthracene series, in 4-substituted 4'-nitrostilbene series, and in 1-(p-nitrophenyl)-4-(p-substituted phenyl)-1,3-butadiene series; its scope and limitations have been examined.The ESR spectrum of the reaction against 4-diethylamino-4'-nitrostilbene was measured to identify an anion radical specied expected for explanation of the mechanism of the dehydrogention reaction.Further, cyclic voltammetric measurements of a series of stilbenes and diphenylacetylenes were carried out in connection with the abovw mechanism.In many cases, interestingly, the use of a large excess of t-BuOH brought about succeeding hydroxylation into the ortho-position of a nitro group on the benzene nucleus.The simple hydroxylation is useful for the synthesis of substituted 5-(arylethynyl)-2-nitrophenols, which are expected to function as non-linear optical materials with the corresponding non-hydroxy compounds.The ultraviolet-visible and fluorescence spectral properties were measured and discussed also with those of the related compounds.
- Akiyama, Shuzo,Tajima, Kunihiko,Nakatsuji, Shin'ichi,Nakashima, Kenichiro,Abiru, Kazuko,Watanabe, Miwa
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p. 2043 - 2052
(2007/10/03)
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- Solvatochromic Behavior of Intramolecular Charge-Transfer Diphenylpolyenes in Homogeneous Solution and Microheterogeneous Media
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A study of the solvatochromic behavior of three charge-transfer polyenes - 4-(N,N-dimethylamino)-4'-nitrostilbene (NNS), 1-(p-(N,N-diphenylamino)phenyl)-4-(p-nitrophenyl)-1,3-butadiene (NND), and 1-(p-(N,N-dimethylamino)phenyl)-6-(p-nitrophenyl)-1,3,5-hex
- Shin, Dong Myung,Whitten, David G.
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p. 2945 - 2956
(2007/10/02)
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- Application of Phase-Transfer Catalysis to the Synthesis of Mono- and Bis-stilbenes and Styryls
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A novel and convenient method has been developed for the synthesis of substituted stilbenes by the condensation of active methyl group in suitably substituted toluenes with aromatic aldehydes in aq. medium at room temperature using benzyltriethylammonium chloride as a phase-transfer catalyst.This method has also been applied for the preparation of heterocyclic styryls and extended to the synthesis of bis-stilbenes and bis-styryls using aromatic dialdehydes in place of monoaldehydes.A comparison of the results shows that the present method is superior to the conventional methods in many respects.
- Lokhande, S. B.,Rangnekar, D. W.
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p. 485 - 488
(2007/10/02)
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- The Synthesis and Photochemistry of p-Dimethylamino-p'-nitrodiphenylethyne: a Push-Pull Acetylene
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The title compound (2) was prepared as a possible precursor to a push-pull cyclobutadiene, and its photochemistry examined under a wide range of conditions.The principal reaction observed was loss of a methyl group, and no evidence for bimolecular reactio
- Gallagher, Michael J.,Noerdin, Hazli
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p. 997 - 1005
(2007/10/02)
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- SEMICONDUCTIVITY OF ORGANIC SUBSTANCES-15
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Part 15 treats compounds related to stilbene. Dark conductivity in diphenylbutadiene and four analogs of stilbene has been examined. The compounds were chosen to reveal the possible effects of a donor and an acceptor group attached to opposite ends of the
- ELEY DD,NEWMAN OMG
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p. 1106 - 1112
(2007/10/05)
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