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1.
4,5-Dihydrofuran-3-carbonitriles 3a-i were obtained through oxidative cyclizations of 3-oxo-3-phenylpropanenitrile 1a, 3-oxo-3-thien-2-ylpropanenitrile 1b, 3-(2-furyl)-3-oxopropanenitirle 1c, 3-(1-benzofuran-2-yl)-3-oxopropanenitrile 1d, and 4,4-dimethyl-3-oxopropanenitrile 1e mediated manganese(III) acetate with 1,1-diphenyl-1-butene 2a and 1,2-diphenyl-1-pentene 2b. The treatments of these 3-oxopropanenitriles with 2-thienyl substituted alkenes such as 2-[(E)-2-phenylvinyl]thiophene 2c, 2-[(E)-1-methyl-2-phenylvinyl]thiophene 2d, and 2-(1-phenylvinyl)thiophene 2e formed 5-(2-thienyl)-4,5-dihydrofuran-3-carbonitriles 3j-r in good yields (45-93%). As a result, 2-thienyl substituted alkenes formed products in higher yields than phenyl substituted derivatives. 相似文献
2.
Earles JC Gordon KC Officer DL Wagner P 《The journal of physical chemistry. A》2007,111(30):7171-7180
A spectroscopic and computational study of a series of 2,5-bis(2-thien-2-ylethenyl) thiophene-based oligomers with a para-R-arylethenyl substituent is reported. The primary aim of this investigation is to increase understanding of how charge moves through these molecules by comparing the neutral and oxidized structures for each molecule. To this end, the B3LYP/6-31G(d) computational method was used to calculate the geometry and vibrational spectra for all molecules considered and their oxidation products. For vibrational data, mean absolute deviations for frequencies between experimental and theoretical results ranging from 2 to 18 cm-1 were obtained. Experimental Raman spectroscopy, in conjunction with calculated bond length analyses, was used to gain an insight into the position and delocalization of the charged defect on the oxidized oligomers. The relative frequencies of different ethylene stretching modes served as a particularly useful probe in this regard. It was found that the ethenyl spacers do not impede pi-electron delocalization and, therefore, give rise to a longer conjugation length relative to the corresponding terthiophenes. Furthermore, the para-R-arylethenyl substituent was found to orientate the charged defect toward a specific region of the 2,5-bis(2-thien-2-ylethenyl)thiophene conjugation path. 相似文献
3.
O. A. Ignatenko M. A. Kuznetsov S. I. Selivanov 《Russian Journal of Organic Chemistry》2007,43(7):1042-1047
Oxidation of N-aminophthalimide with lead tetraacetate in the presence of 2-[(E)-2-arylethenyl]-5-phenyl-1,3,4-oxadiazoles gives the corresponding 2-(3-aryl-1-phthalimidoaziridin-2-yl)-5-phenyl-1,3,4-oxadiazoles. From 2-phenyl-5-[(1E,3E)-4-phenylbuta-1,3-dien-1-yl]-1,3,4-oxadiazole only the addition product at both C=C bonds was obtained, while in the reaction with 2,5-bis[(E)-2-phenylethenyl]-1,3,4-oxadiazole both mono- and bis-adducts were isolated. 相似文献
4.
Salo Gronowitz Marcel Temciuc Anna-Britta Hrnfeldt 《Journal of heterocyclic chemistry》1993,30(4):1111-1116
Reaction between various thienyllithium derivatives and dimethyl disulfide has been used for the preparation of 2,5-, 2,3-, and 3,4-bis(methylthio)thiophenes, as well as 2,3,4- and 2,3,5-tris(methylthio)thiophenes. Bromination of (methylthio)thiophenes with N-bromosuccinimide was found to be most convenient for the preparation of brominated (methylthio)thiophenes such as 3-bromo-2,5-bis(methylthio)- and 5-bromo-2,3-bis(methylthio)thiophene, 3,4-dibromo-2,5-bis(methylthio)-, 2,5-dibromo-3,4-bis(methylthio)- and 2,3-dibromo-4,5-bis(methylthio)thiophene as well as 3-bromo-2,4,5-tris(methylthio)thiophene. The reaction of methylthio substituted thienyllithium derivatives with methyl chloroformate was used for the syntheses of methyl methylthio substituted thiophenecarboxylates and using 1/3 of an equivalent for the direct preparation of methylthio substituted 3-thienylcarbinols as tris[2,4,5-tris(methylthio)-3-thienyl]carbinol. 相似文献
5.
V. I. Potkin S. K. Petkevich P. V. Kurman 《Russian Journal of Organic Chemistry》2010,46(9):1305-1312
Acylation of thiophene and phenol with 3,4,4-trichloro-3-butenoyl chloride afforded the corresponding 1-(thien-2-yl)- and
1-(4-hydroxyphenyl)-3,4,4-trichloro-3-buten-1-ones, whose reaction with amines led to the formation of 3-amino-1-(thien-2-yl,
4-hydroxyphenyl)-4,4-dichloro-2-buten-1-ones The heterocyclization of the initial ketones into pyrazole structure was not
observed, and the reaction with hydrazine hydrate provided bispyrazole products, N,N′-bis(5-thien-2-yl)- and N,N′-bis[5-(4-hydroxyphenyl)-1H-pyrazol-3-ylmethylene]hydrazines. 相似文献
6.
J. Gonzalo Rodriguez Jorge Esquivias Antonio Lafuente Laura Rubio 《Tetrahedron》2006,62(13):3112-3122
Nano conjugated thienylethenyl and thienylethynyl compounds with controlled structure and dimensions have been efficiently prepared, by heterocoupling reaction between 1,4-(thienylethynyl)phenylacetylene (or thienylethenyl)phenylacetylene and 2- or 2,5-dihalothiophene. Conjugated 1,4-di(2-thienylethynylphenyl)- (or 2-thienylethenylphenyl)-1,3-butadiyne were obtained by the homocoupling of the terminal acetylenes in excellent yield. The end-capped (N,N-dimethylaminophenyl)- and [3,5-di(trimethylsilylethynyl)-1-ethynyl]-2,5-di(phenylethynyl)nthiophene were obtained by the heterocoupling between the corresponding terminal acetylene and 2,5-di(iodo)thiophene, catalyzed by the bis(triphenylphosphine)palladium and cuprous iodide system in excellent yield. 相似文献
7.
Dagmar Obendorf Herwig Schottenberger Klaus Wurst Gerhard Laus 《Journal of organometallic chemistry》2005,690(3):811-817
(E)-2-(1′-Formylruthenocenyl)ethenyl-1′,2,2′,3,3′,4,4′,5-octamethylferrocene (1) and (all-E)-2,5-bis[2-[1′-[2-(1′,2,2′,3,3′,4,4′,5-octamethylferrocenyl)ethenyl]ruthenocenyl]ethenyl]thiophene (2) were synthesized by a sequence of Wittig olefinations. The X-ray structure of 1 is reported. The cyclic voltammogram of compound 1 shows the irreversible one-electron transfer expected for ruthenocene and a reversible wave for the octamethylferrocene moiety. Both waves occur at about the same potential as observed for the parent metallocenes. Compound 2, however, exhibits completely unusual redox properties. In contrast to most ruthenocene-containing compounds, a reversible two-electron transfer is observed at a significantly lower potential than found usually for ruthenocenes that can be attributed unambiguously to the independent oxidation/reduction of the two ruthenocene moieties. The unexpected stability of the oxidation products must be due to the presence of the thiophene-ethene bridge, which facilitates the oxidation reaction and stabilizes the reaction products by delocalization of the valence electrons. 相似文献
8.
Syntheses of 2,5-bis(4-methyl-2-thienyl)thiophene 3 and 2,5-bis(4-methyl-2-thienyl)pyrrole 4 are described. The key step involves Stetter reaction between 4-methyl-2-thiophenecarboxaldehyde and divinyl sulfone. Cyclizaton of the resulting 1,4-bis-(4-methyl-2-thienyl)-1,4-butanedione 2 with Lawesson's reagent gives 2,5-bis(4-methyl-2-thienyl)thiophene 3, whereas condensation with ammonium acetate provides the 2,5-bis(4-methyl-2-thienyl)pyrrole 4. 相似文献
9.
Takahito Itoh Toshio Nakamura Masataka Kubo 《Journal of polymer science. Part A, Polymer chemistry》1999,37(15):3027-3039
Novel 2,5-dimethylene-2,5-dihydrothieno[3,2-b]thiophene derivatives such as 2,5-bis[di(ethylthio)methylene]-2,5-dihydrothieno[3,2-b]thiophene ( 4b ) and 2,5-bis[cyano(ethylthio)methylene]-2,5-dihydrothieno[3,2-b]thiophene ( 4c ) were successfully synthesized as isolable crystals. Polymerization behavior of 2,5-bis(dicyanomethylene)-2,5-dihydrothieno[3,2-b]thiophene ( 4a ), 4b , and 4c was investigated. 4a , 4b , and 4c are not homopolymerizable with any initiators and also not copolymerizable with vinyl monomers such as styrene (St), methyl methacrylate, and acryronitrile except for an alternating copolymerization of 4a with St. 4a , 4b , and 4c did not copolymerize with 7,8-bis(butoxycarbonyl)-7,8-dicyanoquinodimethane (BCQ) as a highly conjugated comonomer and instead only homopolymer of BCQ was obtained, indicating that they are much less reactive than BCQ. To obtain the relative reactivity among 1c , 2c , and 4c , the rate of addition reaction of 2,2′-azobis(isobutyronitrile) (AIBN) with 4c was compared with those of AIBN with 7,8-bis(ethylthio)-7,8-dicyanoquinodimethane ( 1c ) and with 2,5-bis[cyano(ethylthio)methylene]-2,5-dihydrothiophene ( 2c ) by NMR spectroscopy and analyzed with the first-order kinetics. The relative reactivity among 1c , 2c , and 4c was found to be as follows: 1c > 4c > 2c . The relationship between structure and reactivity for the quinonoid compounds was discussed. © 1999 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 37: 3027–3039, 1999 相似文献
10.
《Tetrahedron letters》2004,45(38):7061-7064
End-capped (N,N-dimethylaminophenyl) and 2′-thienylethynyl 2,5-thiophene oligomer structures were synthesized by heterocoupling between the terminal acetylenes such as: p-(N,N-dimethylaminophenyl)ethyne (3) [or 1-(p-(N,N-dimethylaminophenyl)-2-p-(ethynylphenyl)ethyne, 4]; p-(β-ethenyl-2′-thienyl)phenylethyne (E-9) [or p-(β-ethynyl-2′-thienyl)phenylethyne, 11], and 2,5-diiodothiophene, catalyzed by the Cl2Pd(PPh3)2/CuI system, in good to excellent yields. The 2,5-di[(3′,5′-di(trimethylsilylethynyl)phenyl]x-1-ethynyl]thiophene oligomers were prepared by heterocoupling between 3′,5′-di[(trimethylsilylethynyl)phenyl]x-1-ethyne (n = 0-2) terminal acetylenes and 2,5-diiodothiophene, in excellent yields. The terminal acetylenes were efficiently prepared by a specific protection-deprotection methodology. All the ethynylphenyl compounds obtained show fluorescence radiation emission, with a bathochromic shift of the wavelength that increases with the chain conjugation. 相似文献
11.
《Journal of organometallic chemistry》1986,312(1):133-137
The synthesis of }2,3,5,6-η4-bicyclo[2.2.1]hepta-2,5-diene}-(E)-bis(2-ethoxy-naphth-1-yl)platinum(II) has been described. As a consequence of the two adjacent naphthalene rings the compound has a stationary E-conformation; there is no rotation about the platinum-carbon σ-bonds. 相似文献
12.
Alexander A. KadyrovDmitrii Silaev Eli BreuerGerd-Volker Röschenthaler 《Journal of fluorine chemistry》2002,114(1):99-101
1,1,3,3,3-Pentafluoro-2-pentafluorophenyl-1,2-epoxypropane 1 reacted with trimethylphosphite giving two diastereomers, (Z)- and (E)-3,6-bis(trifluoromethyl)-3,6-bis(pentafluorophenyl)-1,4-dioxan-2,5-dione 2a, b in a 1:1 ratio, cyclodimerisation product of the intermediately generated α-lactone 4. Compounds 2a, b were hydrolysed to furnish 3,3,3-trifluoro-2-hydroxy-2-(2,3,4,5,6-pentafluorophenyl)propionic acid 5. 相似文献
13.
S. V. Chapyshev 《Russian Chemical Bulletin》2011,60(11):2301-2305
It was shown using IR spectroscopy and ESR spectroscopy that UV irradiation of 2-azido-4,6-dichloro-1,3,5-triazine isolated in solid argon resulted in triplet 4,6-dichloro-1,3,5-tri-azinyl-2-nitrene (D = 1.384 cm?1, E = 0.004 cm?1), whose further photochemical transformation included the consecutive formation of 3-didehydro-1,2,4,6-tetraazepine, 2-chloro-1-diazochloromethyl-2-isocyanocarboimide, and presumably triplet 2-chloro-1-chloromethyl-idene-2-isocyanocarboimide and isocyanodichloroacetonitrile. The photolysis of 2-azido-4,6-dimethoxy-1,3,5-triazine and 2-azido-4,6-di(dimethylamino)-1,3,5-triazine affords photo-chemically stable triplet 4,6-dimethoxy-1,3,5-triazinyl-2-nitrene (D = 1.436 cm?1, E = 0.0044 cm?1) and 4,6-bis(dimethylamino)-1,3,5-triazinyl-2-nitrene (D = 1.468 cm?1, E = 0.0042 cm?1) as the final products. 相似文献
14.
Four polymers based on perylenediimide co-polymerized with thiophene, bithiophene, selenophone and thieno[3,2-b]thiophene were investigated as the acceptor materials in all-polymer solar cells. Two different donor polymers, poly[4,8-bis(5-(2-ethylhexyl)thiophen-2-yl)benzo[1,2-b;4,5-b′]dithiophene-2,6-diyl-alt-(4-(2-ethylhexyl)-3-fluorothieno[3,4-b]thiophene)-2-carboxylate-2,6-diyl](PTB7-Th) and poly[(5,6-difluoro-2,1,3-benzothiadiazol-4,7-diyl)-alt-(3,3′′′-di(2-dodecyltetradecyl)-2,2′;5′,2″;5″,2′′′-quaterthiophen-5,5′′′-diyl)](Pff BT4T-2DT), with suitably complementary absorption spectra and energy levels were applied and examined. Among all different donor-acceptor pairs studied here, the combination of PTB7-Th:poly[N,N′-bis(1-hexylheptyl)-3,4,9,10-perylenediimide-1,6/1,7-diyl-alt-2,5-thiophene](PDI-Th) exhibited the best power conversion efficiency(PCE) of 5.13%, with open-circuit voltage(V_(oc)) = 0.79 V, short-circuit current density(J_(sc)) = 12.35 mA·cm~(-2) and fill-factor(FF) = 0.52. The polymer of PDI-Th acceptor used here had a regio-irregular backbone, conveniently prepared from a mixture of 1,6- and 1,7-dibromo-PDI. It is also noteworthy that neither additive nor posttreatment is required for obtaining such a cell performance. 相似文献
15.
The use of 2-(trimethylsilylethyl)sulfonamide (SES-NH2) has permitted the selective and efficient synthesis of new triolefinic 15-membered azamacrocycles 3. Differential coordination mode with palladium has been observed when macrocycle 3aab [(E,E,E)-1,6-bis(p-tolylsulfonyl)-1,6,11-triazacyclopentadeca-3,8,13-triene] was treated with a palladium(0) or a palladium(II) source. 相似文献
16.
Jingjing Shi Imran Murtaza Shan Shao Xiaosi Zhu Yang Zhao Mengmeng Zhu Osamu Goto Hong Meng 《中国科学:化学(英文版)》2017,60(1):90-98
A couple of novel electrochromic materials poly(2,3,4,5-tetrakis(2,3-hydrothieno[3,4-b]dixin-5-yl)-1-methyl-1H-pyrrole) (P(t-EDOT-mPy)) and poly(5,5′,5′′,5′′′-(thiophene-2,3,4,5-tetrayl)tetrakis(2,3-dihydrothieno[3,4-b][1,4]dioxine)) (P(t-EDOT-Th)) are electrodeposited via multi-position polymerization of their tetra-EDOT substituted monomers t-EDOT-mPy and t-EDOT-Th, respectively. Compared with the linear 2D structured poly(thiophene) (E g=2.2 eV) and poly(2,5-bis(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)thiophene) (E g=1.7 eV), P(t-EDOT-Th) (E g=1.62 eV) has the lowest band gap. Hence, we speculate that the band gaps of the two polymers, having 3D structures, are decreased in contrast to non-substituted polymers or bi-EDOT substituted polymers, thiophene and 1-methyl-1H-pyrrole. The results indicated that P(t-EDOT-Th) thin films are more stable and show higher transmittance amid two polymers, which may find their utilization in organic optoelectronics. 相似文献
17.
V. V. Astakhova M. Yu. Moskalik B. A. Shainyan 《Russian Journal of Organic Chemistry》2017,53(7):981-985
Reactions of trifluoroacetamide with (1E,3E)-1,4-diphenylbuta-1,3-diene and 1,1,4,4-tetraphenylbuta-1,3-diene in the oxidative system t-BuOCl–NaI have been studied. The reaction with (1E,3E)-1,4-diphenylbuta-1,3-diene afforded three products, N,N′-(phenylmethylene)bis(trifluoroacetamide), 3-chloro-4-iodo- 2,5-diphenyl-1-(trifluoroacetyl)pyrrolidine, and trifluoro-N-[(3E)-2-hydroxy-1,4-diphenylbut-3-en-1-yl]acetamide, with a high overall yield. 1,1,4,4-Tetraphenylbuta-1,3-diene failed to react with trifluoroacetamide. 相似文献
18.
Zahra Asadi Mozaffar Asadi Fahimeh Dehghani Firuzabadi Reza Yousefi Mehrnaz Jamshidi 《Journal of the Iranian Chemical Society》2014,11(2):423-429
Some tetradentate N2O2 Schiff base ligands, such as N,N′-bis(naphtalidene)-1,2-phenylenediamine, N,N′-bis(naphtalidene)-4-methyl-1,2-phenylenediamine, N,N′-bis(naphtalidene)-4-chloro-1,2-phenylenediamine, N,N′-bis(naphtalidene)-4-nitro-1,2-phenylenediamine, N,N′-bis(naphtalidene)-4-carboxyl-1,2-phenylenediamine, and their uranyl complexes were synthesized and characterized by 1H NMR, IR, UV–Vis spectroscopy, TG (thermogravimetry), and elemental analysis (C.H.N.). Thermogravimetric analysis shows that uranyl complexes have very different thermal stabilities. This method is used also to establish that only one solvent molecule is coordinated to the central uranium ion and this solvent molecule does not coordinate strongly and is removed easier than the tetradentate ligand and also trans oxides. The electrochemical properties of the uranyl complexes were investigated by cyclic voltammetry. Electrochemistry of these complexes showed a quasireversible redox reaction without any successive reactions. Also, the kinetic parameters of thermal decomposition were calculated using Coats–Redfern equation. According to Coats–Redfern plots the kinetics of thermal decomposition of the studied complexes is first-order in all stages. Anticancer activity of the uranyl Schiff base complexes against cancer cell lines (Jurkat) was studied and determined by MTT (3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyltetrazoliumbromide) assay. 相似文献
19.
Frank Hipler 《Journal of Molecular Structure》2003,658(3):179-191
The synthesis and crystal structures of three mercapto functionalised 1,3,4-thiadiazoles and the crystal structure of 2-mercapto-5-methyl-1,3,4-thiadiazole are described. In the solid state, 2-mercapto-5-methyl-1,3,4-thiadiazole 1 forms a thioamide tautomer as shown by FTIR and Raman spectroscopy as well as X-ray crystallography and as theoretically predicted. The molecules are connected to form chains via N-H?S hydrogen bonds with N?S=328.3 pm. Bis(2-methyl-1,3,4-thiadiazolyl)-5,5′-disulfide 2, the disulfide of 1, as well as 2-(tert-butyldithio)-5-methyl-1,3,4-thiadiazole 3 and 2,5-bis(tert-butyldithio)-1,3,4-thiadiazole 4 have been synthesised and characterised by vibrational spectroscopy and X-ray diffraction. 相似文献