- Polymer-based fluorescence sensor incorporating triazole moieties for Hg2+ detection via click reaction
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The polymer could be obtained by the polymerization of 1,4-dibutoxy-2,5-diethynylbenzene (M-1) with 1,4-diazidobenzene (M-2) via click reaction. The polymer show blue fluorescence. The responsive optical properties of the polymer on various transition metal ions were investigated by fluorescence spectra. Compared with other cations, such as Co2+, Ni2+, Ag+, Cd2+, Cu2+ and Zn2+, Hg2+ can exhibit the most pronounced fluorescence response of the polymer Hg2+ can exhibit the most pronounced fluorescence response of the polymer due to triazole moiety in the polymer main chain as the metal binding ligand. The results indicate this kind of conjugated polymer with triazole moiety synthesized by click reaction can be used as a selective fluorescence sensor for Hg2+ detection.
- Huang, Xiaobo,Meng, Jie,Dong, Yu,Cheng, Yixiang,Zhu, Chengjian
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- In situ Cu(II)-containing chiral polymer complex sensor for enantioselective recognition of phenylglycinol
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A chiral polymer P1 was synthesized by the polymerization of 2,5-dibutoxy-1,4-di(benzaldehyde)-1,4-diethynylbenzene (M-1) with (R,R)-1,2-diaminocyclohexane (M-2) via Schiff's base formation, and the chiral polymer P2 could be obtained by the reduction reaction of P1 with NaBH 4. P2 can serve as a "turn-off" fluorescent sensor toward Cu2+ and Ni2+. The in situ generated Cu(II)-containing polymer complex of P2 (Cu(II)-P2) can exhibit remarkable "turn-on" fluorescence enhancement response and considerable enantioselectivity toward unmodified phenylglycinol via a ligand displacement mechanism. More importantly, (R,R)-Cu(II)-P2 solution can turn on bright blue fluorescence color change again upon addition of l-phenylglycinol under a commercially available UV lamp, which can be clearly observed by the naked eyes for direct visual discrimination at low concentration. The simple, rapid and sensitive benign process makes this protocol promising for recognition of phenylglycinol enantiomers.
- Wang, Lu,Song, Fengyan,Hou, Jiali,Li, Junfeng,Cheng, Yixiang,Zhu, Chengjian
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- Two polymorphs and cocrystal of styryl-pyridine derivatives with tuned emission induced by Co2+ and Zn(phen)32+
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A styryl-pyridine derivative, 2,5-dibutoxy-1,4-bis[2-(4-pyridyl)ethenyl] benzene (L), has been designed and synthesised. Two polymorphs of L and crystals of [Zn(phen)3]2L(ClO4)4 were obtained by different crystallisation conditions. Polymorph-α was prepared by a solvent evaporation method. However, polymorph-β and a cocrystal of [Zn(phen)3]2L(ClO4)4 were obtained by different inducing reagents. It has been found that there are, in total, four independent conformations of the molecule L in the three kinds of crystals. We have calculated the standard molar enthalpy of formation (ΔHm) of each conformation and demonstrated that the stabilisation energy of each conformation significantly relies on both the planarity of the molecules (L) and bond length of conjugated bridges. Furthermore, the photophysical properties of the three kinds of crystals also exhibit differences in the vibration and absorption spectroscopies, solid-state photoluminescence and time-resolved fluorescence, which may arise from the chromophore's stacking modes and the intermolecular electronic interactions in the crystals. These results revealed that the optical properties of functional organic materials could be tuned by controlling their crystallisation environment for a specific molecule. The Royal Society of Chemistry 2014.
- Zhang, Ruilong,Zhang, Qiong,Liu, Zhaodi,Yang, Longmei,Wu, Jieying,Zhou, Hongping,Yang, Jiaxiang,Tian, Yupeng
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- Triphenylamine and terpyridine-zinc(ii) complex based donor-acceptor soft hybrid as a visible light-driven hydrogen evolution photocatalyst
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A donor-acceptor coordination polymer (TPA-Zn) was synthesized by Zn(ii)-assisted self-assembly of an in situ generated triphenylamine (TPA) cored tristerpyridine ligand. The polymer absorbs a broad-spectrum of light and exhibits visible light-assisted hydrogen generation (27.1 mmol g-1 over 9 h) from water with 2.9% quantum efficiency at 400 nm. The microscopy images show a mesoscale fibrous morphology and the Brunauer-Emmett-Teller (BET) analysis reveals the porous nature of TPA-Zn (surface area: 234.5 m2 g; d = 6.98 nm), both of which are helpful for substrate diffusion during catalysis. This journal is
- Ghorai, Manas K.,Kar, Kamal K.,Kumar, Manish,Maji, Tapas Kumar,Samanta, Debabrata,Singh, Sugandha,Verma, Parul
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- Fluorescent bispyrroles. New building blocks for novel π-conjugated polymers
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Several bispyrroles which are bridged through conjugated aromatic moieties were synthesized by the Wittig-Horner-Emmons reaction. Photophysical and electrochemical data of these highly fluorescent monomers reveal that they are useful building blocks for the design of a wide variety of novel π-conjugated polymers, which may find application as potential optoelectronic materials. (C) 2000 Elsevier Science Ltd.
- Eldo,Arunkumar,Ajayaghosh
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- Direct evidence for secondary interactions in planar and nonplanar aromatic π-conjugates and their photophysical characteristics in solid-state assemblies
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Direct evidence for non-covalent secondary interactions in planar and nonplanar aromatic π-conjugates and their solid-state assemblies is established. A series of horizontally, vertically, and radially expanded oligo(phenylenevinylene)s (H-OPVs, V-OPVs, and R-OPVs, respectively) were designed with a fixed π-core and variable alkyl chain lengths on the periphery. Single-crystal structures of the OPVs were resolved to trace the secondary interactions that direct the solid-state self-organization and molecular packing of the chromophores. The H-OPVs were found to be planar, and they did not show any secondary interactions in the crystal lattices. The V-OPVs and R-OPVs were found to be nonplanar and to exhibit multiple CH/π hydrogen-bonding interactions among aryl hydrogen donors and acceptors. The enthalpies of the melting and crystallization transitions revealed that the planar H-OPVs are highly crystalline compared with the nonplanar R-OPVs and V-OPVs. Polarized light microscopy studies revealed the formation of one-dimensional nematic mesophases in H-OPVs. The absolute solid-state photoluminescence quantum yields (PLQYs) of the OPVs were determined using an integrating sphere setup. The highly packed H-OPVs showed low PLQYs compared with those of the weakly packed V-OPVs and R-OPVs. Time-resolved fluorescence decay measurements revealed that the excited-state decay dynamics of highly packed H-OPVs was much faster with respect to their low PLQYs. The decay profiles were found to be relatively slow (with higher life time (τ)) in the V-OPVs and R-OPVs. A field-effect transistor (FET) device was constructed for an OPV sample that showed a hole carrier mobility in the range of 10-5 cm2 V-1 s-1. The present investigation thus provides a new opportunity to trace the role of secondary interactions on π-conjugated mesophase self-assemblies and their solid-state emission and FET devices, more specifically based on OPV chromophores.
- Goel, Mahima,Narasimha, Karnati,Jayakannan, Manickam
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- Solvent-free synthesis of pillar[6]arenes
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An efficient solvent-free procedure for the synthesis of pillar[6]arenes has been developed. The procedure involves the solid-state condensation of finely milled 1,4-dialkoxybenzene and paraformaldehyde by grinding in the presence of a catalytic amount of H2SO4. The use of organic solvents for the extraction of products has also been avoided. Operational simplicity, compatibility with various 1,4-dialkoxybenzenes, non-chromatographic purification technique, high yields and mild reaction conditions are the notable advantages of this procedure. A large scale reaction demonstrated the practical applicability of this methodology.
- Santra,Kopchuk,Kovalev,Zyryanov,Majee,Charushin,Chupakhin
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- Large stokes shift chiral polymers containing (R,R)-salen-based binuclear boron complex: Synthesis, characterization, and fluorescence properties
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Two novel chiral fluorescence polymers P-1 and P-2 incorporating (R,R)-salen-based binuclear boron complex in the main chain backbone were synthesized by (R,R)-salen-based boron complex (M-1) with 9,9-dibutyl-2,7- diethynyl-9H-fluorene (M-2) and 1,4-dibutoxy-2,5-diethynylbenzene (M-3) via Pd-catalyzed Sonogashira coupling reaction, respectively. The chiral polymers were characterized by 1H NMR, UV-vis spectroscopy, photoluminescence (PL), gel permeation chromatography (GPC), TGA, DSC, cyclic voltammetry (CV), and theoretical calculation using density-functional theory (DFT) method. P-1 and P-2 show anisotropic fluorescence property with emission spectral maxima at 474 nm and 514 nm, respectively. Both two chiral polymers can exhibit high fluorescence quantum yields (up to 44% and 52%) with large Stokes shifts over 90 nm. The DFT theoretical calculation of the polymer repeating units indicates that the optical band gaps of P-1 is higher than that of P-2, which was consistent with the CV determination results.
- Ma, Xiao,Jiao, Jiemin,Yang, Jing,Huang, Xiaobo,Cheng, Yixiang,Zhu, Chengjian
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- Protein Adsorption Switch Constructed by a Pillar[5]arene-Based Host-Guest Interaction
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The interfacial properties of solid substrates are of importance for protein adsorption. Herein, we report a reversible protein adsorption switch based on the host-guest interaction of the butoxy pillar[5]arene and adipic acid. By the detector of the contact angle (CA), atomic force microscopy (AFM), and luminoscope on the silicon substrate, the intelligent protein switch exhibits excellent adsorptivity for BSA and switch performance by pH regulation.
- Xiao, Xuan,Nie, Guanrong,Zhang, Xiaoyan,Tian, Demei,Li, Haibing
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- Humidity Sensing through Reversible Isomerization of a Covalent Organic Framework
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Here we report that a covalent organic framework (COF), which contains 2,5-di(imine)-substituted 1,4-dihydroxybenzene (diiminol) moieties, undergoes color changes in the presence of solvents or solvent vapor that are rapid, passive, reversible, and easily detectable by the naked eye. A new visible absorption band appears in the presence of polar solvents, especially water, suggesting reversible conversion to another species. This reversibility is attributed to the ability of the diiminol to rapidly tautomerize to an iminol/cis-ketoenamine and its inability to doubly tautomerize to a diketoenamine. Density functional theory (DFT) calculations suggest similar energies for the two tautomers in the presence of water, but the diiminol is much more stable in its absence. Time-dependent DFT calculations confirm that the iminol/cis-ketoenamine absorbs at longer wavelength than the diiminol and indicate that this absorption has significant charge-transfer character. A colorimetric humidity sensing device constructed from an oriented thin film of the COF responded quickly to water vapor and was stable for months. These results suggest that tautomerization-induced electronic structure changes can be exploited in COF platforms to give rapid, reversible sensing in systems that exhibit long-term stability.
- Jhulki, Samik,Evans, Austin M.,Hao, Xue-Li,Cooper, Matthew W.,Feriante, Cameron H.,Leisen, Johannes,Li, Hong,Lam, David,Hersam, Mark C.,Barlow, Stephen,Brédas, Jean-Luc,Dichtel, William R.,Marder, Seth R.
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- CONSTRUCTION OF A COBALT COORDINATION POLYMER BASED ON A LINEAR LIGAND WITH FLEXIBLE BRANCHED CHAINS
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Abstract: A cobalt coordination polymer based on a linear ligand with flexible branched chains 4,4′-(2,5-dibutoxy-1,4-phenylene)dipyridine (BPDP), namely, {[Co(BPDP)(H2O)4]·2BPDP·2NO3}n, is obtained and characterized by the elemental analysis and single crystal X-ray diffraction. The UV-Visible spectral features are also investigated in details.
- Li, Y. Q.,Qian, J. L.,Zhang, C. L.,Zhou, T.
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p. 918 - 927
(2021/07/29)
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- Fluorescent material with piezochromism and slovatochromism and preparation method thereof
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The invention relates to a fluorescent material with piezochromism and slovatochromism and a preparation method thereof, and belongs to the technical field of fluorescent materials. The fluorescent material with the piezochromism and the slovatochromism comprises a cyano-substituted p-phenylenevinylene compound, and the structural formula of the cyano-substituted p-phenylenevinylene compound is shown in the specification. The invention further discloses a preparation method of the fluorescent material with the piezochromism and the slovatochromism. The fluorescent material has slovatochromism and piezo-chromism performance at the same time, and compared with an existing fluorescent material, the application range is wider, and popularization is facilitated.
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Paragraph 0054-0057; 0075; 0076; 0096; 0097; 0117; 0118
(2021/05/12)
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- Bipyridyl ligand and preparation method thereof, ruthenium supramolecular self-assembly body containing bipyridyl ligand and preparation method and application of ruthenium supramolecular self-assembly
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The invention provides a novel bipyridyl bidentate ligand and a preparation method thereof. The structural formula of the novel bipyridyl bidentate ligand is shown in the specification. The inventionfurther provides a ruthenium supramolecular self-assembly body of the ligand and a preparation method of the ruthenium supramolecular self-assembly body. The preparation method comprises the followingsteps: putting a prepared ruthenium receptor and a bipyridyl ligand into a container, adding a mixed solvent of methanol and dichloromethane in equal proportion, stirring for a period of time at roomtemperature, spin-drying the solution to a certain volume after the reaction is finished, slowly adding diethyl ether, and separating out solid powder, namely the ruthenium supramolecular self-assembly body containing the bipyridyl ligand. The self-assembly body is a novel ruthenium-containing self-assembly compound, and has a good inhibition effect on cancer tumor cell lines A549 and HepG-2.
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Paragraph 0030-0036
(2020/08/18)
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- Boronate Ester-Capped Helicates
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Triple-stranded helicates were obtained by metal-templated multicomponent reactions of bispyridyloxime ligands with arylboronic acids. The helicates feature two hexa-coordinated MII ions (M=Fe, Zn, or Mn), which are embedded in a macrobicyclic ligand framework, and two arylboronate ester capping groups. The latter can be used to introduce functional groups such as pyridines, aldehydes, nitriles, and carboxylic acids in apical position. The functionalized helicates have the potential to be used as nanoscale building blocks for more complex assemblies, as evidenced by the synthesis of a 3 nm-sized trianglimine.
- Depallens, Adrien B.,Fadaei-Tirani, Farzaneh,Giraldi, Erica,Ortiz, Daniel,Scopelliti, Rosario,Severin, Kay
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supporting information
(2020/06/09)
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- Supramolecular enantiomeric and structural differentiation of amino acid derivatives with achiral pillar[5]arene homologs
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Complexation of achiral pillar[5]arenes with chiral amines induced strong circular dichroism (CD) signals. The CD responses differed drastically depending on the nature of the amino acid guest, and they significantly varied and part of them even inverted, upon increasing the length of the alkyl chains of the pillar[5]arenes guests. Accordingly, this tactic allowed for the unprecedented simultaneous enantiomeric and structural differentiation of α-amino esters with homologous molecular hosts.
- Ji, Jiecheng,Li, Yizhou,Xiao, Chao,Cheng, Guo,Luo, Kui,Gong, Qiyong,Zhou, Dayang,Chruma, Jason J.,Wu, Wanhua,Yang, Cheng
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supporting information
p. 161 - 164
(2019/12/30)
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- Role of synergistic π-π Stacking and X-H...Cl (X = C, N, O) H-bonding interactions in gelation and gel phase crystallization
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The self-assembly of p-pyridyl-ended oligo-p-phenylenevinylenes (OPVs) in ethanol leads to the formation of either hollow or solid microrods. The corresponding protonated OPVs with n-butyl chains induce transparent gelation and also gel phase crystallization owing to various synergistic noncovalent interactions. The chloride ion-selective gelation, AIEE and stimuli responsiveness of the gel are also observed. This journal is
- Bhattacharjee, Subham,Bhattacharya, Santanu
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supporting information
p. 7019 - 7022
(2015/04/22)
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- Novel isoindigo-based conjugated polyelectrolytes: Synthesis and fluorescence quenching behavior with water-soluble poly(p-phenylenevinylene)s
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Two novel ID-based water-soluble conjugated polymers (+)-PIDPV and (-)-PIDPV were synthesized by Heck coupling reaction. These two polyelectrolytes are both consisted of isoindigo units and phenylenevinylene units. In the UV-vis absorption spectra, both (+)-PIDPV and (-)-PIDPV exhibit broad absorption bands that almost cover the whole visible region. Photophysical investigations reveal that the fluorescence of water-soluble PPV can be efficiently quenched by oppositely charged PIDPV at a very low concentration. Cationic PPV shows an efficient quenching effect with ΚSV = 1.01 × 106 M-1 in the presence of (-)-PIDPV while the anionic PPV gives a lager quenching constant with ΚSV = 1.71 × 106 M-1 in the presence of (+)-PIDPV. Furthermore, the blend films of water-soluble PPVs and oppositely charged PIDPV also exhibit excellent quenching effect. These properties suggest that (+)-PIDPV and (-)-PIDPV are promising materials in the application of ionic photoactive layer in the organic solar cells.
- Kou, Chun,He, Xiaolong,Jiang, Xueyu,Ni, Yifeng,Liu, Ling,Huangfu, Changxin,Liu, Kuan
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p. 2223 - 2237
(2015/10/05)
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- New water soluble terphenylene diethynylene fluorophores
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Inspired by our earlier works on sensors from dendritic phenyleneethynylenes, two new star-shaped water-soluble fluorophores containing terphenylene diethynylene units and anionic carboxylate peripheries are successfully synthesized. The convergent synthesis relies on Sonogashira cross-coupling reactions between tris-(4-ethynylphenyl)amine and the iodophenyleneethynylene branches. All of the compounds are characterized by 1H, 13C NMR, and mass spectrometry. In aqueous solution, the less polar fluorophore 1 shows lower quantum yield than 2 (18 vs 33 %) as a result of hydrophobic induced aggregation. One of these anionic water-soluble fluorophores exhibits a selective fluorescence quenching by Fe3+ ion in phosphate buffer pH 8.
- Vongnam, Kunnigar,Vilaivan, Tirayut,Sukwattanasinitt, Mongkol,Rashatasakhon, Paitoon
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p. 197 - 202
(2014/03/21)
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- Remarkable regioisomer control in the hydrogel formation from a two-component mixture of pyridine-end oligo(p-phenylenevinylene)s and N-decanoyl-l-alanine
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N-Decanoyl-L-alanine (DA) was mixed with either colorless 4,4′-bipyridine (BP) or various derivatives such as chromogenic oligo(p-phenylenevinylene) (OPV) functionalized with isomeric pyridine termini in specific molar ratios. This mixtures form salt-type gels in a water/ethanol (2:1, v/v) mixture. The gelation properties of these two-component mixtures could be modulated by variation of the position of the "N" atom of the end pyridyl groups in OPVs. The presence of acid-base interactions in the self-assembly of these two-component systems leading to gelation was probed in detail by using stoichiometry-dependent UV/Vis and FTIR spectroscopy. Furthermore, temperature-dependent UV/Vis and fluorescence spectroscopy clearly demonstrated a J-type aggregation mode of these gelator molecules during the sol-to-gel transition process. Morphological features and the arrangement of the molecules in the gels were examined by using scanning electron microscopy (SEM), atomic force microscopy (AFM), and X-ray diffraction (XRD) techniques. Calculation of the length of each molecular system by energy minimization in its extended conformation and comparison with the XRD patterns revealed that this class of gelator molecules adopts lamellar organizations. Rheological properties of these two-component systems provided clear evidence that the flow behavior could be modulated by varying the acid/amine ratio. Polarized optical microscopy (POM), differential scanning calorimetry (DSC), and XRD results revealed that the solid-phase behavior of such two-component mixtures (acid/base=2:1) varied significantly upon changing the proton-acceptor part from BP to OPV. Interestingly, the XRD pattern of these acid/base mixtures after annealing at their associated isotropic temperature was significantly different from that of their xerogels.
- Bhattacharjee, Subham,Datta, Sougata,Bhattacharya, Santanu
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supporting information
p. 16672 - 16681
(2014/01/06)
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- Synthesis, optical and electrochemical properties of novel D-π-A type conjugated polymers based on benzo[c][1,2,5]selenadiazole unit via alkyne module
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Three novel donor-π-acceptor (D-π-A) type conjugated polymers P-1, P-2, and P-3 based on benzo[c][1,2,5]selenadiazole moiety and phenyl or naphthyl group via alkyne module were firstly prepared by Sonogashira-Hagihara reaction of various diiodo aryl compounds with the key monomer 4,7-diethynylbenzo[c] [1,2,5]selenadiazole (M-1), which was synthesized by a strategy of firstly introducing the trimethylsilylacetylene flexible group, and then introducing the selenium atom. The polymers displayed obvious absorption peaks at the region from 503 to 510 nm and narrow orange-red or red fluorescence in the range of 576-595 nm because benzo[c][1,2,5]selenadiazole unit can effectively reduce the lowest unoccupied molecular orbital (LUMO) energy levels of these polymers. The band gaps of these polymers can be tuned in the range of 1.37-1.76 eV by using different aryl donor groups. These findings indicate that these benzo[c][1,2,5]selenadiazole-based conjugated polymers can be developed for excellent fluorescent materials.
- Li, Duanqin,Li, Hui,Liu, Miaochang,Chen, Jiuxi,Ding, Jinchang,Huang, Xiaobo,Wu, Huayue
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p. 6158 - 6164
(2013/10/22)
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- Influence of heteroaryl group on electrochemical and spectroscopic properties of conjugated polymers
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During our search for novel conjugated compounds, novel monomers and their polymers with selenophene and tellurophene group were synthesized and characterized. Conjugated poly(p-phenylenevinylenes)s (PPV) derivatives attracted a large attention due to their photolouminescence properties. The stereocontrolled synthesis of 1,4-bis(2-(heteroar-2-yl) ethenyl)benzenes and 1,4-bis(heteroar-2-yl)benzenes with tellurophene, selenophene, thiophene and furan-based monomers has been successfully performed. Eight of p-phenylene derivatives have been synthesized, electrochemically polymerized and characterized.
- Data, P.,Lapkowski, M.,Motyka, R.,Suwinski, J.
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p. 271 - 282,12
(2020/08/24)
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- Aryl trihydroxyborate salts: Thermally unstable species with unusual gelation abilities
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A series of aryl trihydroxyborate salts were synthesized and found to form gels in benzene. The compounds were thermally unstable and readily underwent protodeboronation in solution and the solid state. Gelation could be induced without decomposition via sonication. Subsequent characterization studies revealed an unusual dependence of gel properties on alkyl chain length.
- Moy, Cheryl L.,Kaliappan, Raja,McNeil, Anne J.
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experimental part
p. 8501 - 8507
(2011/12/04)
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- A highly selective fluorescence-based polymer sensor incorporating an (R,R)-salen moiety for Zn2+ detection
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A chiral polymer incorporating an (R,R)-salen moiety was synthesized by the polymerization of (R,R)-1,2-diaminocyclohexane with 2,5-dibutoxy-1,4- di(salicyclaldehyde)-1,4-diethynyl-benzene by a nucleophilic additionelimination reaction. The fluorescence responses of the (R,R)-salen-based polymer toward various metal ions were investigated by fluorescence spectra. Compared with other cations, such as Na+, K+, Mg2+, Ca 2+, Mn2+, Fe2+, Fe3+, Co 2+, Ni2+, Cu2+, Ag+, Cd 2+, Hg2+, and Pb2+, Zn2+ can lead to a pronounced fluorescence enhancement as high as 7.8-fold together with an obvious blue-shift change of the chiral polymer. More importantly, the fluorescent color of the polymer changed to bright blue instead of weak yellow after addition of Zn2+, which can be easily detected by the naked eye. The results indicate that this kind of chiral polymer, incorporating an (R,R)-salen moiety as a receptor in the main chain backbone, can exhibit high sensitivity and selectivity for Zn2+ recognition.
- Xu, Ying,Meng, Jie,Meng, Lingxing,Dong, Yu,Cheng, Yixiang,Zhu, Chengjian
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scheme or table
p. 12898 - 12903
(2011/02/23)
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- METHODS AND COMPOSITIONS FOR CONTROL OF CABBAGE LOOPER, Trichoplusia ni
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The invention provides in part dialkoxybenzene compounds for controlling infestation by a Trichoplusia ni, and methods thereof. The compounds include a compound of Formula I: where R1 may be methyl, ethyl, propyl, n-butyl, isopentyl(3-methylbutyl) or allyl; R2 may be at positions 2, 3 or 4 and may be H, methyl, ethyl, propyl, n-butyl, isopentyl(3-methylbutyl) or allyl; and R3 may be optionally present at positions 2, 3 and 4, and is allyl; except that when R2 is at position 2, R3 if present is at position 3, and when R2 is at position 3, R3 if present is at positions 2 or 4, and when R2 is at position 4, R3 if present is at position 2, and when R2 is at position 4 and R3, if present, has reacted with an OH group at position 1 in a Markovnikov sense, then R3 becomes R4, a dihydrofuran.
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Page/Page column 9; 11
(2010/07/04)
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- METHODS AND COMPOSITIONS FOR CONTROL OF GYPSY MOTHS, Lymanria dispar
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The invention provides in part dialkoxybenzene and eugenol compounds for controlling infestation by a Lymantria dispar, and methods thereof. The compounds include a compound of Formula I: where R1 may be methyl, ethyl, propyl, n-butyl, isopentyl (3-methylbutyl) or allyl; R2 may be at positions 2, 3 or 4 and may be H, methyl, ethyl, propyl, n-butyl, isopentyl (3-methylbutyl) or allyl; and R3 may be optionally present at positions 2, 3 and 4, and is allyl; with the provisos that when R2 is at position 2, R3 if present is at position 3, or when R2 is at to position 3, R3 if present is at positions 2 or 4, or when R2 is at position 4, R3 if present is at position 2; or of Formula II: where R1 may be methyl, ethyl, propyl, n-butyl, isopentyl (3-methylbutyl) or allyl; or mixtures thereof.
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Page/Page column 12
(2010/08/07)
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- METHOD FOR PRODUCING AROMATIC COMPOUND POLYMER
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A method for producing an aromatic compound polymer comprising oxidatively polymerizing one or more of aromatic compound(s) having two or more hydrogen atoms directly connected to aromatic ring(s), in the presence of an oxidizing agent, wherein the method employs a catalyst composed of a transition metal complex or a catalyst prepared from a transition metal complex and an activating agent, and said catalyst has a parameter P defined by the following formula (A) of 0.50 or more, and a parameter Eo defined by the following formula (B) of 0.50 [V] or more: P=Af/Ai (wherein Ai represents an absorbance at an absorption maximum belonging in an absorption band located at the longest wavelength side in an absorption spectrum obtained for a solution containing the catalyst, in a ultraviolet to near-infrared wavelength region from 200 nm to 800 nm, and Af represents an absorbance at the same wavelength applied to the Ai, in an absorption spectrum in the above wavelength region obtained for a solution prepared by adding 3 equivalent of water per mole of the metal contained in the catalyst to the solution), and Eo=Epa+Epc/2V (wherein, Epa represents a peak potential at the oxidation side of an oxidation-reduction potential derived from the transition metal contained in the catalyst, at a potential of 0.50 [V] or more based on oxidation-reduction potential of ferrocene/ferrocenium ion measured with a cyclic voltammetry for the solution containing the catalyst, and Epc represents a peak potential at the reduction side corresponding to Epa by the same measurement).
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- Terpyridine-platinum(ii) acetylide complexes bearing pendent coordination units
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Platinum(ii) complexes bearing various alkyne-pyrene, alkyne-4′-terpyridine and alkyne-dibutoxyphenylacetylide-terpyridine units were constructed in a step-by-step procedure based on copper-promoted cross-coupling reactions with preconstructed modules; formation of bis(ligand) complexes of Fe(ii) and Zn(ii) by binding of the pendent terpyridine units provided heterotrinuclear derivatives, all of which exhibit highly structured absorption features in solution and display a rich electrochemistry due to the presence of various redox active modules. The Royal Society of Chemistry 2006.
- Ziessel, Raymond,Diring, Stephane,Retailleau, Pascal
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p. 3285 - 3290
(2007/10/03)
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- The synthesis and conformation of oxygenated trianglimine macrocycles
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The synthesis of series of D2h and C2v symmetric oxygenated aromatic dicarboxaldehydes, using dilithiation methodology, is described along with their reactivity in the [3 + 3] cyclocondensation reaction with (1R,2R)-diaminocyclohexane to give oxygenated trianglimine macrocycles. Macrocycles derived from C2v symmetric dialdehydes give macrocycles with a stereogenic aromatic plane with complete diastereocontrol, as a mixture of retainers.
- Kuhnert, Nikolai,Lopez-Periago, Ana,Rossignolo, Giulia M.
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p. 524 - 537
(2007/10/03)
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- Zinc-catalyzed Williamson ether synthesis in the absence of base
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A zinc-catalyzed Williamson ether synthesis is described with microwave heating in the presence of DMF or stirring in an oil-bath using THF as solvent and in the absence of base. Zinc powder was found to be a highly efficient catalyst for the synthesis of aromatic ethers using microwave heating in the presence of N,N-dimethylformamide as well as under stirring in an oil-bath using tetrahydrofuran as solvent without any inorganic base. This method can be used for selective mono-, di- or tri-O-alkylations.
- Paul, Satya,Gupta, Monika
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p. 8825 - 8829
(2007/10/03)
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- The preparations and some properties of mixed aryl-thienyl oligomers and polymers
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The syntheses by transition metal coupling reactions of a large number of oligomers constructed from benzene and thiophene rings are described. The first use of arylcadmium chlorides for such coupling reactions is reported. The routes chosen allow for rational variation in the modes of linkage, the substitution and the proportions of the two units. The benzene and thiophene rings are always joined in a known order and may bear a wide variety of regularly spaced functional groups. Additionally the shape of the oligomers may be varied at will. In all cases p-type doping with iodine or ferric chloride leads to large enhancements in conductivity.
- Pelter, Andrew,Jenkins, Ieuan,Jones, D. Elfyn
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p. 10357 - 10400
(2007/10/03)
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- Alkoxylated p-phenylenevinylene oligomers: Synthesis and spectroscopic and electrochemical properties
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Twenty-one n-alkoxy substituted phenylenevinylene oligomers were synthesized, varying in size, number and position of the OR groups. IR,MS and solubility data are presented. NMR measurements provided the molecular structure as well as information about conformations and molecular dynamics. UV and of cyclic voltammetric data give correlations of chemical structure (number and position of OR substituents) with separate HOMO and LUMO energies.
- Ndayikengurukiye, Henri,Jacobs, Sven,Tachelet, Wim,Van Der Looy, Johan,Pollaris, Anne,Geise, Herman J.,Claeys, Magda,Kauffmann, Jean M.,Janietz, Silvia
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p. 13811 - 13828
(2007/10/03)
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- Fluorescence Studies of Poly(p-phenyleneethynylene)s: The Effect of Anthracene Substitution
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The poly(p-phenyleneethynylene) molecules, PI-PIII, synthesized by a palladium-catalyzed cross-coupling reaction of diiodobenzene derivatives and derivatives of 1,4-diethynylbenzene, are highly luminescent materials.The polymers are soluble by virtue of the -OC16H33 groups introduced on the aromatic rings and by controlling their molecular weight.The fluorescent quantum yields are between 0.35 and 0.40 depending on the material.The excited-state lifetimes of the polymers are 1-2 ns, slightly shorter than that of the model compund, 1,4-diphenylethynyl-2,5-dibutoxybenzene, which has a lifetime of 3 ns.Incorporation of anthracene, coupled at the 9,10-positions by using 9,10-dibromoanthracene, into the polymer backbone decreases the quantum yield to between 0.05 and 0.27 depending on the anthracene content.In addition, low-energy electronic transitions and longer wavelength emission bands associated with the anthracene group are produced.The polymers harvest optical energy and transfer it to the anthracene resulting in emission from this chromophore.In the case where only terminal anthracene units, introduced by using 9-bromo-10-phenylethynylanthracene, are present, the process is very efficient with >95percent of the energy being transferred to the end groups.
- Swager, Timothy M.,Gil, Caroline J.,Wrighton, Mark S.
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p. 4886 - 4893
(2007/10/02)
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- Phase transfer catalysis without solvent. Alkylation of phenol and derivatives
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The alkylation of phenol, hydroquinone and p-aminophenol is performed by phase transfer catalysis without solvent. High yields of α,ω-diphenoxyalkanes, hydroquinone diethers and high selective mono O-alkylation of p-aminophenol are obtained in very mild conditions.
- Loupy,Sansoulet,Diez-Barra,Carrillo
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p. 1465 - 1471
(2007/10/02)
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- The Electrochemical Metoxylation of Dialkoxyaromatic Compounds and the Determination of Isomer Ratios by N.M.R. Spectroscopy
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Electrolysis in methanol-KOH solution of p-diethoxy-, p-di-n-propoxy-, p-di-isopropoxy-, p-di-n-butoxy-, p-di-isobutoxy-, and p-di-s-butoxy-benzenes afforded the corresponding 3,6-dialkoxy-3,6-dimethoxy-cyclohexa-1,4-diene, shown by 1H n.m.r. spectroscopy to be an approximately equimolar mixture of cis- and trans-isomers.Likewise, from 9,10-diethoxyanthracene was obtained an equimolar mixture of the cis- and trans-isomers of 9,10-diethoxy-9,10-dimethoxy-9,10-dihydroanthracene.
- Elgy, Geraldine M.,Jennings, W. Brian,Pedler, Alan E.
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p. 1255 - 1260
(2007/10/02)
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- Gas-Liquid Phase-transfer Synthesis of Phenyl Ethers and Sulphides with Carbonate as Base and Carbowax as Catalyst
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When a mixture of a phenol (or thiol) and an alkyl halide is passed, in the gaseous state, through a solid bed of potassium carbonate (or sodium hydrogencarbonate) and catalytic amounts of Carbowax 6000, contained in a glass column at 170 deg C, the corresponding ethers (or sulphides) may be collected at the outlet.The Carbowax acts in a similar manner to the crown ethers used in solid-liquid phase-transfer catalysis.The potassium carbonate-Carbowax combination allows the generation of anions up to pKa of ca. 12.The catalysis mechanism is discussed and the synthesis of several ethers and thioethers is reported, some of which are obtained only with difficulty by normal liquid-liquid phase-transfer catalysis.
- Angeletti, Enrico,Tundo, Pietro,Venturello, Paolo
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p. 1137 - 1142
(2007/10/02)
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- Cyclohexene-(1)-dione-(3,6)-tetraalkyldiketals and process
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Cyclohexene-(1)-dione-(3,6)-tetraalkyldiketals of the formula STR1 wherein each R is a primary or secondary C1-4 alkyl radical are obtained by catalytic hydrogenation of p-benzoquinone tetramethyl-diketal with about 1 mol of H2 per mole of diketal, in a basic medium, at a temperature of from about -10° to +150° C. and optionally by reketalization with a primary or secondary C2-4 alcohol in a slightly acid medium with substantial exclusion of water, at a temperature of from about -10° to +35° C. Cyclohexene-(1)-dione-(3,6)-tetraalkyldiketals, optionally dissolved in an alcohol ROH give hydroquinone dialkyl ethers on acidification and heating to about 60° to 120° C., which ethers are valuable dyestuff intermediates. On catalytic hydrogenation in a basic medium, cyclohexene-(1)-dione-(3,6)-tetraalkyldiketals give the corresponding cyclohexane-(1,4)-tetraalkyldiketals, which are the starting products for the manufacture, for example, of tetracyanoquinodimethane, an important compound in the field of semiconductors.
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