Corannene-based cage compound, molecular capsule, preparation method and application thereof
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A technology of cage compounds and compounds, applied in the field of supramolecular chemical material technology and organic synthesis
Inactive Publication Date: 2019-07-12
BEIJING NORMAL UNIVERSITY
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Embodiment 1
[0090] Synthesis of an example compound 1A in the cage compound based on corannene and its application in the separation of fullerenes, the structural formula of the compound formula (1A) is as follows:
[0091]
[0092] according to figure 1 Shown synthetic route, the compound shown in preparation formula (1A), concrete steps are as follows:
[0093] 1) Add 3-bromo, 5-hydroxypyridine (2g, 11.5mmol), compound shown in formula (6) (n=3, 5.5g, 17.2mmol), K 2 CO 3 (4.8g, 34.5mmol) and DMF (40ml); mix well and heat to 70°C, stir for 16 hours; after the reaction is cooled to room temperature, add 40ml of water, extract three times with ethyl acetate, combine the organic phases, wash with saturated saline Wash twice, add anhydrous Na 2 SO 4 Dried, filtered and then spin-dried, purified and separated by a silica gel column to obtain 3g of a colorless oily product compound shown in formula (9) (R is an ether oxygen chain, n=3), with a yield of 81.7%; the structural verification...
Embodiment 2
[0113] The synthesis of an example of compound 1B in the cage compound based on corannene and its application in the separation of fullerenes, the structural formula of compound 1B is as follows:
[0114]
[0115] The specific implementation method is the same as in Example 1, only the compound shown in the formula (6) in step 1) is replaced by iodoisobutyl, and the synthetic route is as follows Figure 15 As shown, the compound shown in formula (1B) is obtained.
Embodiment 3
[0117] Repeat Example 1, the only difference is: R is a kind of alkyl chain or hydrogen atom, m=1, 2, 3, 4, 5, 6, 7, 8, 9 or 10, technical effect and embodiment 1 approx.
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Abstract
The invention discloses a cage compound based on a corannulene, a molecular capsule formed by the cage compound and fullerene, a preparation method and application thereof, wherein the cage compound based on the corannulene has a structure shown in the formula (1) shown in the specification. In the formula (1), a is equal to 0 or 1, X=O or NH, Y is one of an ether oxygen chain, an alkyl chain or ahydrogen atom, and n and m are integers greater than or equal to zero. The cage compound has a unique curved structure and has a cage structure with a certain size of cavity; the cage structure provided in the present invention has a cavity size matching with C60 and C70, can be respectively complexed with the C60 and the C70 to obtain C60 capsules and C70 capsules, can also be selectively complexed with the C60 to obtain the single C60 capsules by temperature regulation; and the C60 capsules and the C70 capsules obtained in the present invention can achieve capsule dissociation to release the C60 and the C70, so that extraction and separation and purification of the fullerene can be achieved.
Description
technical field [0001] The invention belongs to the field of supramolecular chemical material technology and organic synthesis, and in particular relates to a cage compound based on corannene, a molecular capsule formed by the cage compound and fullerene, a preparation method and an application. Background technique [0002] Since the discovery of fullerenes in 1985, representative C 60 and C 70 Because of its special structure and properties, it has important research value and application prospects in the fields of materials, chemical biology and other sciences, and has received extensive attention and research. Therefore, in order to purify and separate fullerenes, the selective recognition of fullerenes is particularly important. [0003] Currently in this field, most are based on calixarenes (E. Huerta, G.a. Metselaar, A. Fragoso, E. Santos, C. Bo and J. de Mendoza, Selective Binding and Easy Separation of C70 by Nanoscale Self-Assembled Capsules, Angew .Chem.,Int.Ed...
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