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Transition-metal-salt-mediated radical reactions of fullerenes have attracted extensive attention as a new and important method for fullerene functionalization. The application of relatively cheap and easily available ferric perchlorate (Fe(ClO 4 ) 3 ) to the synthesis of [60]fullerene (C 60 ) has demonstrated remarkable advantages and afforded a series of novel fullerene derivatives. In this review we present our recent progress in this area and summarize the reactions of C 60 with malonate esters, β-keto esters, nitriles, aldehydes/ketones, and arylboronic acids in the presence of Fe(ClO 4 ) 3 to afford the C 60-fused disubstituted lactones, C 60-fused hemiketal, C 60-fused dihydrofuran, C 60-fused oxazoles, C 60-fused 1,3-dioxolanes, and fullerenyl boronic esters. The possible reaction mechanisms for the above-mentioned reactions are also described in detail. 相似文献
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I. P. Romanova O. G. Sinyashin G. G. Yusupova V. I. Kovalenko Yu. Ya. Efremov Yu. V. Badeev I. I. Vandyukova I. A. Arakelyan 《Russian Chemical Bulletin》1999,48(11):2144-2148
The reaction of [60]fullerene with diphenylphosphinoyl azide in toluene or ino-dichlorobenzene in the presence of traces of water affords 2-[N-(diphenylphosphoryl)amino]-1-hydroxy[60]fullerene This reaction in THF gives a mixture of (N-diphenylphosphoryl)[60]fullerenol[1,2-b]aziridine and a product of partial hydrolysis of the bisadduct of phosphorylated azide and fullerene.
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2168–2172, November, 1999. 相似文献
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Romanova I. P. Yusupova G. G. Nafikova A. A. Kovalenko V. I. Sinyashin O. G. 《Russian Chemical Bulletin》2002,51(8):1491-1496
A single di(azahomo)[60]fullerene isomer was prepared for the first time by the reaction between [60]fullerene and isocyanurato-substituted azide. The structure of the product was established by 1H and 13C NMR, UV, and IR spectroscopy. 相似文献
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Masaki Ozawa Jing Li Kentaro Nakahara Lixin Xiao Hiroharu Sugawara Koichi Kitazawa Kazushi Kinbara Kazuhiko Saigo 《Journal of polymer science. Part A, Polymer chemistry》1998,36(17):3139-3146
A novel series of polyamides having [60]fullerene moieties in the main chain were synthesized by a direct polycondensation of [60]fullerenobis(acetic acid) or [60]fullerenobis(acetic acid)/isophthalic acid mixture with a diamine in the presence of triphenyl phosphite and pyridine. Various properties of the polyamides were characterized by means of IR, GPC, TGA, DSC, UV–visible, and photoluminescence. The molecular weight Mw of the [60]fullerene-containing polyamides was observed in the range from about 300,000 to 3,000; upon the changing of the ratio of [60]fullerenobis(acetic acid)/isophthalic acid in the starting mixture, the resulting Mw decreased with increasing the ratio. Most of the thermal and optical properties gradually changed as the ratio changed; the major optical absorption band in visible range exhibited a significant tailing, which shifted toward a longer wavelength, while the photoluminescence spectrum red-shifted with increasing [60]fullerene content. © 1998 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 36: 3139–3146, 1998 相似文献
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The homodinuclear bismetallacyclopropa[60]fullerene complexes (η2-C60)M(μ-η1,η1-trans-Ph2PCHCH PPh2)2M(η2-C60) (1, M = Pt; 2, M = Pd) were prepared by reaction of C60 with M(dba)2 (dba = dibenzylideneacetone) and trans-1,1′-bis(diphenylphosphino)ethylene in 82% and 92% yield, whereas reaction of C60 with Pd(dba)2 and trans-dppet followed by treatment with C60 and Pt2(dba)3 gave rise to the heterodinuclear complex (η2-C60) Pd(μ-η1,η1-trans-Ph2PCHCH PPh2)2Pt(η2-C60) (3) in 65% yield. Mechanistic study showed that these reactions involve the intermediates of monometallacyclopropa[60]fullerene diphosphine ligands (η2-C60)M(η1-trans-Ph2PCHCHPPh2)2 (4, M = Pt; 5, M = Pd). All the mono- and bismetallacyclopropa[60]fullerene complexes 1-5 have been fully characterized by elemental analysis and spectroscopy, as well as for 2 by X-ray crystallography. 相似文献
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Romanova I. P. Kalinin V. V. Nafikova A. A. Yakhvarov D. G. Zverev V. V. Kovalenko V. I. Rusinov G. L. Plekhanov P. V. Charushin V. N. Sinyashin O. G. 《Russian Chemical Bulletin》2003,52(1):173-178
The reaction of [60]fullerene with 2-azidopyrimidines affords fullerenoimidazopyrimidines, whose electron affinity is higher than that of nonmodified C60. 相似文献
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Romanova I. P. Yusupova G. G. Nafikova A. A. Yakhvarov D. G. Larionova O. A. Sinyashin O. G. 《Russian Chemical Bulletin》2004,53(1):144-147
A reaction of [60]fullerene with O,O-dibutyl azidophosphate affords a first representative of phosphorylated azahomo[60]fullerenes, which is easier to reduce electrochemically than the starting C60. 相似文献
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The synthesis of a new linear benzo[3]phenylene-[60]fullerene dyad 1 is achieved over 10 steps in 15% overall yield by using an efficient sequence combining a double cobalt(I)-mediated cyclotrimerization with a Bingel reaction. 相似文献
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单加成环丙烷富勒烯膦酸酯衍生物的合成与电化学性能 总被引:1,自引:0,他引:1
在Mn(OAc)3•2H2O催化下, C60分别和亚甲基二膦酸四乙酯、氰基亚甲基膦酸二乙酯或乙氧羰基亚甲基膦酸二乙酯在氯苯中回流, 生成3个单加成环丙烷富勒烯膦酸衍生物C60C(R)PO(OEt)2 [1, R=PO(OEt)2; 2, R=COOEt; 3, R=CN]. 与以前报道的Bingel反应法相比, 该方法副产物少并且缩短了反应时间. 采用循环伏安法发现1, 2的还原电位相对于C60发生负移, 而3的还原电位相对于C60却正移40 mV, 表明引入象氰基一样具有很强吸电子能力的取代基团, 可以改善富勒烯球的电化学性能, 合成电子接受能力较强的富勒烯衍生物. 相似文献
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《高分子科学杂志,A辑:纯化学与应用化学》2013,50(12):1263-1273
Abstract A new synthetic approach for the fabrication of core‐shell like conducting elastomers was described. The approach utilized the facile intermolecular self‐assembly of poly(dimethylsiloxane) (PDMS) in DMSO leading to formation of a core particle, while soluble oligoaniline (A x ) segments dispersed in the solution phase resembling a shell overlayer for building the morphology. This morphology was demonstrated by bis[penta(tetraanilinofullereno)] bis(aminopropyl)poly(dimethylsiloxane) [PDMS‐(F5A4)2] triblock co‐oligomers synthesized using a functionalized C60 derivative as a linker. Observation of 1H NMR spectroscopic responses on the PDMS particle formation in DMSO‐d 6 is consistent with the proposed core‐shell geometry with oligoaniline moieties located at the shell overlayer. 相似文献
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Atsushi Ikeda Masaru Kawaguchi Yoshio Suzuki Tsukasa Hatano Munenori Numata Seiji Shinkai Akio Ohta Makoto Ohta 《Journal of inclusion phenomena and macrocyclic chemistry》2000,38(1-4):163-170
The calixarene-fullerene interaction,which causes only a slight change in the absorptionspectra, has been substantiated by calorimetricmeasurements: the H° values arecomparable with those obtained from the associationconstants estimated by a spectroscopic method. Furthermore, we determined the association constantbetween homooxacalix[3]arene and [60]fullerenederivatives with a porphyrin moiety by fluorescencespectra. 相似文献
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Study of the factors determining the outcome of cycloaddition of isocyanurato-substituted azides to [60]fullerene 总被引:2,自引:0,他引:2
Sinyashin O. G. Romanova I. P. Yusupova G. G. Nafikova A. A. Kovalenko V. I. Azancheev N. M. Fattakhov S. G. Reznik V. S. 《Russian Chemical Bulletin》2001,50(11):2162-2171
The final outcome of cycloaddition of isocyanuratoalkyl azides to C60 depends on the temperature, the thermal stability of azides, the substituents in the isocyanurate ring, and the number of methylene groups in the alkyl radical. The thermal transformations of the monoadducts obtained were studied. 相似文献
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New stable [6,6]-methano cycloadducts and fulleropyrazolines containing electron-withdrawing groups have been obtained by the reaction of ethyl diazopyruvate with [60]fullerene. The results obtained by a systematic study conducted both in thermal and catalytic conditions have provided crucial indications concerning the mechanism of this important cluster opening process in fullerene chemistry. 相似文献
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V. V. Kutyreva E. A. Shchupak V. L. Karnatsevich N. L. Bazyakina O. N. Suvorova 《Russian Chemical Bulletin》2005,54(6):1535-1536
The Prato reaction was used to synthesize a monoammonium derivative of fullerenopyrrolidine.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1491–1492, June, 2005. 相似文献
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Yu Chen Yun Zhao Ruifang Cai Zu-En Huang Lixiang Xiao 《Journal of Polymer Science.Polymer Physics》1998,36(14):2653-2663
The novel C60–styrene copolymers with different C60 contents were prepared in sodium naphthalene-initiated anionic polymerization reactions. Like the pure polystyrene, these copolymers exhibited the high solvency in many common organic solvents, even for the copolymer with high C60 content. In the polymerization process of C60 with styrene an important side reaction, i.e., reaction of C60 with sodium naphthalene, would occur simultaneously, whereas crosslinking reaction may be negligible. 13C-NMR results provided an evidence that C60 was incorporated covalently into the polystyrene backbone. In contrast to pure polystyrene, the TGA spectrum of copolymer containing ∼ 13% of C60 shows two plateaus. The polystyrene chain segment in copolymer decomposed first at 300–400°C. Then the fullerene units reptured from the corresponding polystyrene fragments attached directly to the C60 cores at 500–638°C. XRD evidence indicates that the degree of order of polymers increases with the fullerene content increased in terms of crystallography. Incorporation of C60 into polystyrene results in the formation of new crystal gratings or crystallization phases. In addition, it was also found that [60]fullerene and its polyanion salts [C60n−(M+)n, M = Li, Na] cannot be used to initiate the anionic polymerization of some monomers such as acrylonitrile and styrene, etc.© 1998 John Wiley & Sons, Inc. J. Polym. Sci. B Polym. Phys. 36: 2653–2663, 1998 相似文献
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[2+2] click chemistry followed by Prato reaction is reported the first time for energy level tunable functionalization of C60. The novel kind of D–A–A C60 charge-transfer complexes exhibits strikingly enhanced optoelectronic properties and significant third-order nonlinear optical potentials. Meanwhile, structures of the ‘click’ C60 products were fully characterized by NMR, IR, and MS. By introducing TCNE, TCNQ, F4-TCNQ click monomers, we obtained energy level tunable fullerene derivatives in high solubility, which was beneficial for processing. Furthermore, UV–vis spectra were enlarged with end-absorptions into the near infrared region, indicating excellent nonlinear optical properties. The electrochemical properties have been studied by cyclic voltammograms, which were in good correlation with the optical spectroscopic and DFT data. 相似文献
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I. P. Romanova V. F. Mironov O. A. Larionova V. I. Morozov V. V. Zverev O. G. Sinyashin 《Russian Chemical Bulletin》2008,57(1):209-211
Fullerene C60 reacts with phosphorous acid triamides to give the radical anion.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 201–203, January, 2008. 相似文献