Pyridine quinoxaline double pillar [n] aromatic hydrocarbon based nanoparticle, and preparation method and applications thereof

[0043] Pyridinequinoxaline double pillar [n]arene host H(R 1 For the synthesis of methoxy group; n=4;), the synthetic route is as follows:

[0044]

[0045] (1) Synthesis of compound 1-2

[0046]

[0047] Compound 1-2 was synthesized by Williamson reaction. A mixture of compound 1-1 (1.2g, 1.6mmol) and benbromophenylboronate (1.4g, 4.8mmol) was dissolved in 30mL DMF, and NaH (0.38g, 16mmol) was added to create an alkaline environment. Mix the solution in N 2 Heated to 80°C under protection for 16 hours. After the reaction was finished, the solution was concentrated by rotary evaporation, and the crude product was purified by column chromatography (PE / DCM / EA, 10 / 1 / 1 as eluent) to obtain 1.2 g of pure product as a white powder. Yield: 76%.

[0048] (2) Synthesis of target product H

[0049]

[0050] The target product H (pyridinequinoxaline bispyra[n]arene host H) was synthesized by Suzuki reaction. Compound 1-2 (1.9g, 2mmol) described in step (1), compound

[0058] The pyridinequinoxaline double-cavity host molecule H prepared in Example 1 and the fluorescent guest molecule G2 have carried out ultraviolet-visible absorption light test respectively (H and G2 are dissolved in chloroform and tested, and the chloroform solution concentration of H is 10 μ M; G2 Chloroform solution concentration is 10 μ M, and test temperature is room temperature) and fluorescence emission spectrum test (H and G2 are dissolved in chloroform to test, and the chloroform solution concentration of H is 10 μ M; The chloroform solution concentration of G2 is 0.1 μ M, and test temperature is room temperature), measure The obtained UV-Vis absorption spectrum and fluorescence emission spectrum are overlaid, such as figure 1 shown.

[0059] from figure 1 It can be seen that the fluorescence emission of the pyridinequinoxaline double-cavity host molecule H overlaps very well with the ultraviolet absorption spectrum of the fluorescent guest molecule G2, both of which

[0061] The pyridinequinoxaline double-cavity host molecule H prepared in Example 1 and the non-fluorescent guest molecule G1 and the fluorescent guest molecule G2 were prepared in chloroform according to the molar ratio [H]:[G1]:[G2]=100:30:5 Mixing in the medium to prepare a mixed solution before the formation of nanoparticles, and then pour into double-distilled water containing surfactants to form nanoparticles (fluorescent nanoparticles) based on pyridinequinoxaline bicolumn [n]arene. Concrete preparation process comprises the following steps:

[0062] (1) Add host molecule H (pyridylquinoxaline double-cavity host molecule H) and non-fluorescent guest molecule G1, fluorescent guest molecule G2 into chloroform respectively, mix well, and prepare chloroform solutions of host molecule H, non-fluorescent The chloroform solution of the guest molecule G1 and the chloroform solution of the fluorescent guest molecule G2; the concentration of the three in chloroform is 10 -3 M.

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