- Synthesis, electronic structure, linear and nonlinear photophysical properties of novel asymmetric branched compounds
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A series of novel asymmetric branched compounds that utilize a 1,3,5-triazine core and feature D-π-A-(π-D′-π-A′)0-2 configurations (D = donor, A = acceptor, π = conjugated bridge) were designed, successfully synthesized, and fully characterized by 1H NMR, 13C NMR, FT-IR, and HRMS. Their photophysical properties including linear absorption, one-photon excited fluorescence, two-photon absorption, and frequency up-converted fluorescence, were systematically investigated in different solvents. With a rise in the polarity of solvents, the peak positions of the one-photon excited fluorescence are red-shifted and the Stokes shifts increase, while the linear absorption wavelengths change slightly. In addition, the target compounds except CZ show the positive solvatokinetic effect. With a rise in the number of branches, the red shifts of the absorption and emission maxima, the hyperchromicity of the molar absorption coefficients, and the decrease of the Stokes shifts are observed. The peripheral electron donors (carbazole, phenothiazine) and acceptors (pyridine, benzimidazole) also exert an important influence on the photophysical properties. Under excitation of 690–930 nm fs laser pulses, all the target compounds emit frequency up-converted fluorescence with the maximal peaks at 471–575 nm, and the two-photon absorption cross-sections in THF are 132 (PTZ), 182 (CZ), 453 (CZ-Py1), 844 (CZ-Py2), 1244 (CZ-BI1), and 2072 (CZ-BI2) GM, respectively. Their two-photon response is found to be nearly additive with respect to the number of branches. The time-dependent density functional theory calculations were conducted to gain an insight into their electronic structures and to better understand the structure-photophysical property relationships. The results clearly indicate the importance of appropriate structural units on the enhancement of two-photon absorption properties.
- Cai, Zhi-Bin,Chen, Li-Jun,Li, Sheng-Li,Ye, Qing,Tian, Yu-Peng
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- Multiple fluorescence ΔcIE and ΔrGB codes for sensing volatile organic compounds with a wide range of responses
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A highly luminescent compound, stilbene-2,4-dimethyl-6-(1,2,2,4- tetramethyl-1,2-dihydroquinolin-6-yl)-1,3,5-s-triazine (MQT), exhibits solvent polarity-induced emission enhancement. A fluorescent sensor array was fabricated with MQT and porous polymer substrates. The colorimetric changes of the array exposed to VOCs can be readily distinguished by the naked eye. Post-processing procedures proved the high selectivity of the array for VOCs. The Royal Society of Chemistry 2011.
- Tian, Kaijun,Hu, Dehui,Hu, Rui,Wang, Shuangqing,Li, Shayu,Li, Yi,Yang, Guoqiang
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- Continuous detection of HCl and NH3 gases with a high-performance fluorescent polymer sensor
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A novel fluorescent triazine-based covalent organic polymer (COP-1) sensor for HCl and NH3 gases has been designed and synthesized. Both the COP-1 powders that were dispersed in solvents and the COP-1 film that was formed on the surface of quartz sheets exhibited stable fluorescence and a sensitive HCl/NH3 response. Immersion in HCl-bubbled solvents weakens and red-shifts the fluorescence emission of the COP-1 powders, owing to a protonation-induced charge transfer (CT). Subsequent injection of NH3 into the solvents recovers the fluorescence via deprotonation. Interestingly, the microporous COP-1 film also shows a similar fluorescence response to HCl/NH3 gas, with high sensitivity and good reversibility, which suggests that it could serve as a solid-state optical probe for continuous and quantitative detection of HCl and NH3 gases. The formation of the red-shifting hydrogen bonds is found to be the origin of the response.
- Xu, Ning,Wang, Rui-Lei,Li, Dong-Peng,Zhou, Zi-Yan,Zhang, Tian,Xie, Yu-Zhong,Su, Zhong-Min
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Read Online
- A METHOD OF PREPARING 5-ALKYLTETRAZOLE
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The present invention relates to a method of preparing 5-alkyltetrazole which comprises the following steps: a) reacting alkyl imidate represented by chemical formula 1 with a1) hydrazine to obtain a compound represented by chemical formula 2; a2) reacting the compound represented by the chemical formula 2 with a nitrite compound and acid, to obtain a reaction mixture; and b) reacting the reaction mixture with a base to obtain 5-alkyltetrazole represented by chemical formula 3.COPYRIGHT KIPO 2018
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Paragraph 0069-0070; 0074-0075
(2018/05/03)
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- A chemical precursor for depositing Sb2S3 onto mesoporous TiO2 layers in nonaqueous media and its application to solar cells
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Deposition of nanocrystalline Sb2S3 onto a mesoporous TiO2 photoanode is an important process in the fabrication of Sb2S3-sensitized solar cells. In order to generate oxide-free nanosized Sb2S3, a single-source precursor for the chemical bath deposition of Sb2S3 in nonaqueous media, Sb(iii)(thioacetamide)2Cl3, was synthesized and used to produce high-quality Sb2S3 for solar cells.
- Maiti, Nilkamal,Im, Sang Hyuk,Lim, Choong-Sun,Seok, Sang Il
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p. 11569 - 11572
(2013/02/23)
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- Synthesis, tunable two and three-photon absorption properties of triazine derivatives by branches
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Three novel triazine derivatives, (E)-4-(2-(4,6-dimethyl-1,3,5-triazin-2- yl)vinyl)- N,N-di-p-tolylaniline (a), 4,4′-((1E,1′E)-(6-methyl-1,3, 5-triazine-2,4-diyl) bis(ethene-2,1-diyl))bis(N,N-di-p-tolylaniline) (b), and 4,4′,4′′-((1E,1′E,1′′E)-(1,3,5- tri
- Zeng, Shuiming,Ouyang, Xinhua,Zeng, Heping,Ji, Wei,Ge, Ziyi
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scheme or table
p. 290 - 295
(2012/05/05)
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- Combinatorial synthesis of 3,5-Dimethylene substituted 1,2,4-Triazoles
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Combinatorial cyclizations of imidates and hydrazides with methylene linked R groups, generated from the corresponding nitriles and carboxylic acids, respectively, provided a large library of 3,5-dimethylene substituted 1,2,4- trizoles. 2011 Bentham Science Publishers Ltd.
- Woodard, Scott S.,Jerome, Kevin D.
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experimental part
p. 132 - 137
(2012/04/18)
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- SUBSTITUTED IMIDAZOLONE DERIVATIVES, PREPARATIONS AND USES
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The present invention relates to polysubstituted imidazolone derivatives, to the pharmaceutical compositions comprising them and to the therapeutic uses thereof in the human and animal health fields. The present invention also relates to a process for preparing these derivatives.
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Page/Page column 37-38
(2010/02/16)
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- PYRAZOLO`1,5-A!`1,3,5! TRIAZIN -4-ONE DERIVATIVES AS CB1 RECEPTOR ANTAGONISTS
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Compounds of Formula (I) are described herein. The compounds have been shown to act as cannabinoid receptor ligands and are therefore useful in the treatment of diseases linked to the mediation of the cannabinoid receptors in animals.
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Page/Page column 47
(2010/02/12)
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- Cannabinoid receptor ligands and uses thereof
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Compounds of Formula (I) that act as cannabinoid receptor ligands and their uses in the treatment of diseases linked to the mediation of the cannabinoid receptors in animals are described herein.
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- Pop-the-Cork strategy in synthetic utilization of imines: Stabilization by complexation and activation via liberation of the ligated species
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Treatment of trans-[PtCl4(RCN)2] (R = Me, Et) with ethanol allowed the isolation of trans-[PtCl4{E-NH=C(R)OEt}2]. The latter were reduced selectively, by the ylide Ph3P=CHCO2Me, to trans-[PtCl2{E-NH=C(R)OEt}2]. The complexed imino esters NH=C(R)OEt were liberated from the platinum(II) complexes by reaction with 2 equiv of 1,2-bis (diphenylphosphino)ethane (dppe) in chloroform; the cationic complex [Pt(dppe)2]Cl2 precipitates almost quantitatively from the reaction mixture and can be easily separated by filtration to give a solution of NH=C(R)OEt with a known concentration of the imino ester. The imino esters efficiently couple with the coordinated nitriles in trans-[PtCl4(EtCN)2] to give, as the dominant product, [PtCl4{NH=C(Et)N=C(R)OEt}2] containing a previously unknown linkage, i.e., ligated N-(1-imino-propyl)-alkylimidic acid ethyl esters. In addition to [PtCl4{NH=C(Et)N= C(Et)OEt}2], another compound was generated as the minor product, i.e., [PtCl4(EtCN){NH=(Et)N=C(Et)OEt}], which was reduced to [PtCl2(EtCN){NH=C(Et)N=C(Et)OEt}], and this complex was characterized by X-ray singlecrystal diffraction. The platinum(IV) complexes [PtCl4{NH=C(Et)N=C(R)OEt}2] are unstable toward hydrolysis and give EtOH and the acylamidine complexes trans-[PtCl4{Z-NH=C(Et)NHC(R)O}2], where the coordination to the Pt center results in the predominant stabilization of the imino tautomer NH=C(Et)NHC(R)=O over the other form, i.e., NH2C(Et)=NC(R)=O, which is the major one for free acylamidines. The structures of trans-[PtCl4{Z-NH=C(Et)NHC(R)=O}2] (R = Me, Et) were determined by X-ray studies. The complexes [PtCl4{NH=C(Et)N=C(R)OEt}2] were reduced to the appropriate platinum(II) compounds [PtCl2{NH=C(Et)N=C(R)OEt}2], which, similarly to the appropriate Pt(IV) compounds, rapidly hydrolyze to yield the acylamidine complexes [PtCl2{NH=C(Et)NHC(R)=O}2] and EtOH. The latter acylamidine compounds were also prepared by an alternative route upon reduction of the corresponding platinum(IV) complexes. Besides the first observation of the platinum(IV)-mediated nitrile-imine ester integration, this work demonstrates that the application of metal complexes gives new opportunities for the generation of a great variety of imines (sometimes unreachable in pure organic chemistry) in metal-mediated conversions of organonitriles, the storage of imino species in the complexed form, and their synthetic utilization after liberation.
- Bokach, Nadezhda A.,Kukushkin, Vadim Yu.,Haukka, Matti,Frausto da Silva, Joao J. R.,Pombeiro, Armando J. L.
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p. 3602 - 3608
(2008/10/08)
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- Activation of acetonitrile in [Cp*Ir(η3-CH2CHCHPh)(NCMe)]+: Crystal structures of iridium-amidine, imino-ether, amido, and amide complexes
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Reactions of [Cp*Ir(η3-CH2CHCHPh)(NCMe)]OTf (1) with protic amines, alcohols, and water produce amidine complexes [Cp*Ir(η3-CH2CHCHPh)(NH=C(NR2)Me)]OTf (2) (R2 = (Me)2 (a), (Me)(H) (b), (i-Pr)(H) (c), (-CH2(CH2)3CH2-) (d)), imino-ether complexes [Cp*Ir-(η3-CH2CHCHPh)(NH=C(OR′)Me)]OTf (4) (R′ = Me (a), Et (b), i-Pr (c)), and amido complex Cp*Ir(η3-CH2CHCHPh)(NHC(=O)Me) (5-K), respectively. The keto form amido complex 5-K undergoes tautomerization to give the enol form complex Cp*Ir(η3-CH2CHCHPh)(N= C(OH)Me) (5-E) in polar solvents. Tertiary amines (NMe3, NEt3) react with 1 in chlorinated solvents (XCl) to give the chloro complex Cp*IrCl(η3-CH2CHCHPh) (3) and quaternary ammonium salts [R3NX]OTf(R = Me, Et and X = CH2Cl, CH3, CHCl2, CCl3, PhCH2). Crystal structures of 2a, 4a, 5-K, and [Cp*Ir(NH=C(OH)Me)(OH2)(PPh3)]OTf2 (6) have been determined by single-crystal X-ray diffraction analysis, which lead us to suggest hybrid structures, Ir--NH-C(=N+Me2)Me (2a′) for 2a and Ir--NH-C(=O+Me)Me (4a′) for 4a to some extent. Complexes 2 and 4 react with PPh3 to give an iridium(III) complex [Cp*Ir(η3-CH2CHCHPh)(PPh3)]OTf (7) and the free amidines NH=C(NR2)Me (8) and imino-ethers NH=C(OR′)Me (9), respectively. Nitrile complexes 1 and [Cp*Ir(η3-CH2CHCHPh)(NCCH= CHMe)]OTf(10) catalyze the hydration of the nitriles in the presence of Na2CO3 to produce amides, and the benzonitrile complex [Cp*Ir(η3-CH2CHCHPh)(NCPh)]OTf(11) catalyzes the methanolysis of benzonitrile in the presence of Na2CO3 to produce NH=C(OMe)Ph. Plausible mechanisms for these catalytic reactions are suggested with the amido and imino-ether complexes such as 4 and 5 being involved.
- Chin, Chong Shik,Chong, Daesung,Lee, Byeongno,Jeong, Hyunmok,Won, Gyongshik,Do, Youngkyu,Park, Young Ja
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p. 638 - 648
(2008/10/08)
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- Aminoacid derivatives as no synthase inhibitors
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Compounds of formula (I) and salts, esters and amides thereof, wherein R1 is a C1-6 straight or branched chain alkyl group, a C3-6 cycloalkyl group, a thiol group optionally substituted by a C1-6 alkyl group, or an amino group optionally substituted by one or two alkyl or alkenyl groups; R2 is H, C1-7 straight or branched chain alkyl, C3-6 cycloalkyl, C2-7 alkenyl or benzyl; A is a 5 or 6 membered aromatic carbocyclic or heterocyclic ring which may optionally be substituted by one or more suitable substituents such as C1-6 alkyl, C1-6 alkoxy, hydroxy, halo, nitro, cyano, trifluoro C1-6 alkyl, amino, C1-6 alkylamino or di C1-6 alkylamino; r is 0, 1 or 2; their use in medicine and in particular for conditions requiring inhibition of the NO Synthase enzyme, pharmaceutical formulations and processes for the preparation thereof are disclosed. STR1
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- A Facile and Concise Synthesis of 2-Alkyl- and 2-Aryl-4-oxo-4H-thiopyranopyridines
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2-Alkyl- and 2-aryl-4-oxo-4H-thiopyranopyridine can be conveniently prepared by reacting the appropriate aromatic and aliphatic O-ethyl thiocarboxylates with the sodium derivative of various alkyl 3-(2-bromopyridyl) ketones.
- Couture, Axel,Grandclaudon, Pierre,Huguerre, Eric
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p. 456 - 457
(2007/10/02)
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- Synthesis and Structure of Alkyl N-Acylimidates
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Alkyl N-acylimidates 1 are prepared more easily and in higher yields than before by reaction of alkyl imidate hydrochlorides 5 with acyl halides 7 in the presence of 2.2 mol of base (14 examples).The X-ray analysis of a crystalline derivative (1dbd) shows, that the C=N- and C=O parts are twisted significantly (torsional angle 77.6 deg).The stereochemical, dynamic and electronic properties of the compounds 1 are interpreted by means of ab initio 3-21 G calculations on conformers of the parent system HO-CH=N-CH=O (8).Low rotational (ca. 6 kcal/mol) and inversional (max. 8 kcal/mol) barriers indicate the many favourable electronic interactions between the C=N- and the C=O groups in such N-functionalised imine derivatives.The compound 1 are significantly higher in energy than bisacylamines and are therefore suggested to be superior, more reactive synthetic C-N-C building blocks.The spectroscopic properties (IR, 13C- and 1H NMR, MS) are given and discussed.
- Kupfer, Rainer,Nagel, Michael,Wuerthwein, Ernst-Ulrich,Allmann, Rudolf
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p. 3089 - 3104
(2007/10/02)
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