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Fullerene dipolymer derivative and preparation method thereof
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A technology of fullerene dimers and derivatives, which is applied in the preparation of halogenated hydrocarbons, chemical instruments and methods, hydrocarbons, etc., and can solve problems such as limitations
Inactive Publication Date: 2013-10-16
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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Therefore, in order to obtain a relatively stable RC 60 - intermediate, the R substituent group with large steric hindrance must be selected to prevent S N 2 reactions occur, thus limiting the selection of raw materials for the synthesis of single-bond fullerene dimers and the synthesis of RC 60 -C 60 Types of R-type fullerene derivatives
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[0034] The invention discloses a preparation method of fullerene dimer derivatives, comprising the following steps:
[0035] 1,2-HRC 60 mixed with the electrolyte solution to obtain the first mixed solution, the R being PhCH 2 , 4-CH 3 PhCH 2 or 4-BrPhCH 2 ;
[0036] The first mixed solution is subjected to electrolytic reduction treatment, and the 1,2-HRC in the first mixed solution 60 Revert all to RC 60 2-· , to obtain the second mixed solution;
[0037] Oxidation treatment is carried out on the second mixed solution, and the RC 60 2-· Oxidation to neutrality gives fullerene dimer derivatives.
[0038] The above-mentioned processes for preparing fullerene dimer derivatives are all carried out under the protection of a protective gas, and the protective gas is preferably an inert gas or nitrogen.
[0039] The present invention has no limitation on the steric hindrance of R, which may be a group with small steric hindrance or a group with large steric hindrance. I...
Embodiment 1
[0047] Add 100mg 1,2-(PhCH 2 )HC 60 , to obtain the first mixed solution;
[0048] in N 2 Under the protection of , with a saturated calomel electrode as a reference electrode, a reduction potential of -0.90V is applied to the first mixed solution for controlled potential electrolysis, to 1,2-(PhCH 2 )HC 60 All are reduced to stop electrolysis to obtain the second mixed solution;
[0049] Adjust the voltage to 0.4V, oxidize the second mixed solution until the solution is neutral, remove the solvent by rotary evaporation, wash with methanol to remove TBAP, filter, and then dry in a vacuum oven to obtain a crude reaction product;
[0050] Using Buckyprep as the separation column and toluene as the mobile phase, high performance liquid chromatography was used for separation and purification to obtain two isomeric PhCH 2 C 60 -C 60 CH 2 Mixture of Ph.
[0051] image 3 It is the electrochemical cyclic voltammogram of this embodiment. Figure 4 Two isomeric PhCH prepared...
Embodiment 2
[0057] Take 100mL 0.02M TBAPF 6 The benzonitrile solution is an electrolyte solution, and the preparation method is the same as in Example 1, and a fullerene dimer derivative is prepared.
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Abstract
The invention discloses a fullerene dipolymer derivative and a preparation method thereof. The method comprises the followings steps of: in the process of oxidizing RC60<2-.> to neutral, firstly oxidizing RC60<2-.> into RC60-; and continually oxidizing the RC60<-> to neutral to obtain the fullerene dipolymer derivative. Compared with the prior art, the method has the advantages: 1,2-HRC60 is taken as a raw material, other reactive substances are not added, and an electrochemical method is adopted, so that the RC60<-> exists stably in a mixed solution without undergoing side reactions such as SN2 and the like, and the preparation method provided by the invention does not have any limit on the space steric hindrance of an R-substituted group. As proved by an experimental result, PhCH2C60-C60CH2Ph can be prepared with the method.
Description
technical field [0001] The invention relates to the technical field of fullerene dimer derivatives, in particular to a fullerene dimer derivative and a preparation method thereof. Background technique [0002] Fullerene (C 60 ) dimer is the precursor for the preparation of fullerene polymers (Martín et al. Chem.Rev.2006, 106, 5136-5190), and plays an important role in the research of fullerene derivatives (Komatsu et al. Nature 1997, 387, 583-586). In addition, fullerene dimers have unique electronic and optical properties, for example, C 60 -Tetrathiafulvalene-C 60 two C's in 60 Can double the lifetime of the charge-separated state (Martín et al. Org.Lett.2005, 7, 1691-1694); in molecular electronics, C 60 Dimers have better binding ability to metal molecules than thiols, and have potential application value for the synthesis of molecular wires (Martín et al. J. Am. Chem. Soc. 2008, 130, 13198-13199). [0003] RC connected with a single bond 60 -C 60 R-type fulleren...
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