共查询到20条相似文献,搜索用时 15 毫秒
1.
Kashiki T Kohara M Osaka I Miyazaki E Takimiya K 《The Journal of organic chemistry》2011,76(10):4061-4070
Two dimers (2 and 3), dendritic tetramer (4), hexamer (5), and decamer (6) of benzo[1,2-b:3,4-b':5,6-b']trithiophene (BTT), a potential π-core unit with C(3h) symmetry, were synthesized, characterized, and evaluated for possible use as organic semiconductors. Single crystal X-ray analyses of the dimers (2 and 3) revealed that they have planar molecular structures with dihedral angles of almost 180° between two BTT units. In accordance with the rigid and planar molecular structure, the unsubstituted dimer (2) is poorly soluble, whereas the octyl-substituted dimer (3) has improved solubility. Although the solubility of the dendritic tetramer (4) is decreased, further extended systems, i.e., the dendritic hexamer (5) and decamer (6), have solubilities better than that of 4. With increasing numbers of BTT units in the molecule, the experimentally determined energy levels of HOMO shift upward slightly and the HOMO-LUMO energy gaps become smaller, but the extent of HOMO destabilization and reduction of the HOMO-LUMO gap are not significant. Taking into account the energy levels of the frontier orbitals, 3-6 could be useful as p-channel organic semiconductors rather than n-channel. In fact, the spin-coated thin film of 3 with edge-on molecular orientation acted as an active channel of field-effect transistors that showed hole mobilities as high as 0.14 cm(2) V(-1) s(-1), indicating that the BTT core is a useful π-conjugated system for application to organic semiconductors, although 4-6 gave FET characteristics rather inferior to those of 3, owing to their amorphous nature in the thin film state. 相似文献
2.
Huang S Xiao Z Wang F Zhou J Yuan G Zhang S Chen Z Thiel W von Ragué Schleyer P Zhang X Hu X Chen B Gan L 《Chemistry (Weinheim an der Bergstrasse, Germany)》2005,11(18):5449-5456
[60]Fullerene mixed peroxides C60(O)(OOtBu)4 exhibit chemo- and regioselective reactions under mild conditions. The epoxy moiety is opened by ferric chloride to form vicinal hydroxy chloride C60Cl(OH)(OOtBu)4. BF3 is also effective in opening the epoxy moiety. The O-O bond of the fullerene mixed peroxide is cleaved by aluminum chloride to form both [5,6]- and [6,6]-fullerene hemiketals (oxohomo[60]fullerenes). A Hock-type rearrangement is proposed for the formation of the hemiketals, in which a fullerene C-C bond is cleaved. Lewis acids and/or visible light can initiate isomerization of the hemiketal isomers. Single-crystal X-ray analysis and theoretical calculations confirmed the results. 相似文献
3.
4.
Bruno Delest Jean-Michel Robert Marie-Renée Nourrisson Muriel Duflos Pierre Renard 《Tetrahedron》2004,60(29):6079-6083
The synthesis of a novel tetracyclic structure, 8,9-dihydroimidazo[4,5-c]pyrrolo[3,2-g]quinolin-4(5H)-one, has been achieved by a convergent pathway. Coupling of the weakly nucleophilic hindered aromatic amine with 1-benzylimidazole-4-carboxylic acid, 7, afforded the corresponding amide 9 using a DCP/DMF complex; subsequent Heck-type arylation leading to desired tetracyclic molecule imidazo[4,5-c]-pyrrolo[3,2-g]quinolin-4(5H)-one. 相似文献
5.
Andre Rosowsky Katherine K. N. Chen May Lin Marilyn E. Nadel Richard St. Amand Sandra A. Yeager 《Journal of heterocyclic chemistry》1971,8(5):789-795
Three 2,4-diamino-l(), 11-dihydro-9H-benzo[3,4]cyclohepta[ 1,2-d]pyrimidines (6a-6c) representing the first examples of a new ring system were synthesized from 2-benzosuberones and cyanoguanidine. Similarly, 2,4-diamino-6,7-dihydro-5H-benzo[3,4]cyelohepta[2,1-d]pyrimidine ( 24 ) was prepared from 1-benzosuberone. The ultraviolet spectral properties of these compounds were examined with reference to those of the analogs in which the central ring is five- and six-mernbered. 相似文献
6.
Ricardo C. Calhelha 《Tetrahedron letters》2010,51(2):281-283
Two methyl 3-aminothieno[3,2-b]pyridine-2-carboxylates were prepared from 3-fluoro or 3-nitropicolinonitriles and methyl thioglycolate in DMF/KOH(aq). From the unsubstituted precursor in the pyridine ring, di(hetero)arylamines were obtained by C-N Buchwald-Hartwig coupling with bromonitrobenzenes and with 2-bromopyridine. In the latter case a tetracyclic compound was formed by intramolecular cyclization. Using a brominated derivative in the pyridine ring as a coupling component, it was possible to synthesize C-C (Suzuki and Sonogashira) and C-N (Buchwald-Hartwig) coupling products and a tetracyclic compound obtained by bifunctionalization of the thienopyridine system. 相似文献
7.
We report herein an effective method for the construction of 4- and 7-ring benzo-fused thieno[3,2-b]thiophenes, involving palladium-catalyzed intramolecular decarboxylative arylation as the key step. 相似文献
8.
Hassan Bohra Hui Chen Yanfen Peng Amsalu Efrem Feng He Mingfeng Wang 《Journal of polymer science. Part A, Polymer chemistry》2018,56(22):2554-2564
Wide-bandgap π-conjugated donor-acceptor (D-A) alternating copolymers consisting of benzo[1,2-c:4,5-c']dithiophene-4,8-dione (BDTD) as the electron-accepting building block have demonstrated outstanding performances in organic bulk heterojunction (BHJ) solar cell devices. But the synthesis of these polymers has been largely limited to conventional polymerization techniques, particularly Stille-coupling based polycondensations, which often involve tedious preactivation of C-H bonds using highly flammable reagents such as butyl lithium and highly toxic reagents such as trialkyl tin chlorides. Herein, we report a “greener” synthetic route of direct arylation polymerization to a series of wide bandgap D-A copolymers with a common acceptor building block of BDTD. The structure–property relationship in these polymers is characterized. We also present the device performances of these polymers in both thin-film field-effect transistors and organic BHJ solar cells involving the BDTD-based polymers as the electron donors and fullerene derivatives as the electron acceptors. © 2018 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2018 , 56, 2554–2564 相似文献
9.
Van Baelen G Kuijer S Rýček L Sergeyev S Janssen E de Kanter FJ Maes BU Ruijter E Orru RV 《Chemistry (Weinheim an der Bergstrasse, Germany)》2011,17(52):15039-15044
Compared with the widespread use of carbonylative Pd-catalyzed cross-coupling reactions, similar reactions involving isocyanide insertion are almost virgin territory. We investigated the intramolecular imidoylative cross-coupling of N-(2-bromoaryl)amidines, leading to 4-aminoquinazolines. After thorough optimization of the reaction with respect to palladium source and loading, ligand, base, temperature, and solvent, a small library of 4-aminoquinazolines was prepared to determine the scope of this method. Various substituents are tolerated on the amidine and the isocyanide, providing efficient access to a broad range of diversely substituted 4-aminoquinazolines of significant pharmaceutical interest. 相似文献
10.
The synthesis of 10H-pyrrolo[1,2-a]thieno[3,4-e][1,4]diazepin-5(4H)-one ( 16 ) and some derivatives are described from methyl 3-bromomethylthiophene-4-carboxylate ( 5 ). The key step of these sequences is the intramolecular cyclization of the carbonylazides 12 and 13 . 相似文献
11.
Florian Beuerle Dr. Andreas Hirsch Prof. Dr. 《Chemistry (Weinheim an der Bergstrasse, Germany)》2009,15(30):7447-7455
New [3:3]hexakisadducts 3 , 6 , and 7 have been synthesized by a stepwise addition of two tripodal malonate tethers to pristine [60]fullerene. For the first time, [3:3]hexakisadducts of two sets of asymmetrically substituted malonate addends could be prepared as single in/out isomers by following this synthetic protocol. Thereby, four spherically defined addend zones I–IV were created with various similar degrees of latitude on the fullerene sphere. Four amphiphilic [3:3]hexakisadducts 12 , 14 , 18 , and 19 were prepared with different relative arrangements of both the hydrophilic and lipophilic moieties in the addend zones I / II and III / IV , respectively. 相似文献
12.
Takashi Hirota Kimiko Katsuta Tetsuto Namba Kenji Sasaki Shhei Hayakawa 《Journal of heterocyclic chemistry》1985,22(1):187-190
Benz[h]imidazo[1,2-c]quinazolinium-l-olate (5) and benzo[h]pyrrolo[1′,2′:3,4]imidazo[1,2-c]quinazolinium-8-olate (9) having novel meso-ionic ring systems were synthesized by the reaction of N-(5,6-dihydrobenzo[h]-quinazolin-4-yl)amino acids with acetic anhydride. 相似文献
13.
1 INTRODUCTION 2-Aminochromene is an important class of com- pounds found as the main compounds of many natu- rally occurring products employed as cosmetics and pigments and utilized as potential biodegradeable agro- chemicals[1~3]. In recent years, montmorillonite in natural and ex- changed forms has received considerable attention in different organic syntheses because of its environ- mental compatibility, low cost, high selectivity, reusa- bility and operational simplicity[4], such as … 相似文献
14.
15.
Cyclization of thioglycolic acids derivatives 3a-d gave isoindolo[1,2-b]thieno[2,3(3,2 or 3,4)-e][1,3]-thiazocines 4a-d . Isoindolo[2,1-a]thieno[2,3(3,2 or 3,4)-f][1,4] or [1,5]diazocines 10b or 11a-c were synthesized from Beckmann or Schmidt rearrangement of the ketones 7a-c . 相似文献
16.
17.
The formation of (E)-3-{2-(2,5-diphenylpyrazolo[1,5-c]pyrimidin-7-yl)hydrazono}indolin-2-ones 3 has been achieved by condensation of equimolar amounts of 7-hydrazino-2,5-diphenylpyrazolo[1,5-c]pyrimidine (1) and isatin (or isatin derivatives) 2 at room temperature. The (E)-products could be isomerized into corresponding the (Z)-3 isomers. Reactions of the latter fused heterocyclic hydrazones towards different electro-philic reagents yielded the corresponding 3-substituted derivatives 4-7. Dehydrative cyclisation of the hydrazones 3 using phosphorus oxychloride afforded the 2,5-diphenyl- indolo[2,3-e]pyrazolo[1',5':3",4"]pyrimido[2",1"-c][1,2,4] triazines 13. The polyfused heterocyclic ring system 13 underwent electrophilic substitution reactions at position 4 rather than at position 3. The 3-bromo isomer of 17 was prepared by a sequence of reactions starting from 2,5-diphenylpyrazolo[1,5-c]pyrimidine-7(6H)-thione (11). The orientation of the electrophilic attack was supported by spectroscopic and chemical evidence. Some of the synthesized compounds were found to possess slight to moderate activity against the microorganisms Bacillus subtilis, Micrococcus luteus, Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa. 相似文献
18.
19.
Yoshinori Tominaga Jiann-Kuan Luo Lyle W. Castle Raymond N. Castle 《Journal of heterocyclic chemistry》1993,30(1):267-273
The synthesis of the novel pyrazolo[4′,3′:5,6]pyrido[2,3-d]pyridazine ring system and some of its derivatives has been accomplished such as 4-amino-1-phenyl-5,8-dioxo-, 4-amino-5,8-dioxo-, 1-phenyl-5,8-dioxo-, 5,8-dioxo-, 5,8-dichloro-1-phenyl-, 5-ethoxy-1-phenyl- and 8-ethoxy-1-phenylpyrazolo[4′,3′:5,6]pyrido[2,3-d]pyrid-azines. 相似文献