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Cucurbit [7] uril [3] rotaxane as well as preparation method and application thereof

A seven-membered cucurbit ring, rotaxane technology, applied in chemical instruments and methods, instruments, analytical materials and other directions, can solve the problem that the detection of amino acid molecules has not yet been reported, and achieve the effects of superior selection performance, low detection limit and high sensitivity

Inactive Publication Date: 2015-03-25
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there have been reports on the seven-membered cucurbitanyl-fluorescent supramolecular system as a molecular probe, but the detection of amino acid molecules based on the cucurbitane rotaxane system as a fluorescent molecular probe has not been reported yet.

Method used

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  • Cucurbit [7] uril [3] rotaxane as well as preparation method and application thereof
  • Cucurbit [7] uril [3] rotaxane as well as preparation method and application thereof
  • Cucurbit [7] uril [3] rotaxane as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Example 1: Synthesis of the guest N,N'-dihexanoic acid-1,2-bis(4-pyridyl)ethylene bromide (G)

[0039] In a 25 mL flask, add 182 mg (1.0 mmol) of 1,2-bis(4-pyridyl)ethylene and 546 mg (3.0 mmol) of bromohexanoic acid in 15 mL of DMF solution, N 2 Heating and reflux reaction under protection for 24 h, cooling after the reaction is complete, suction filtration, dissolving the precipitate in water to crystallize, washing with distilled water, washing with acetone, and drying to obtain the guest N,N'-dihexanoic acid-1,2-bis(4 -pyridyl) vinyl bromide G 400 mg, yield 70%. 1 H NMR (D 2 O, 400MHz) δ: 8.67(d, 4H, ArH), 8.07(d, 4H, ArH), 7.71(s, 2H, CH=CH ), 4.43 (t, 4H,CH 2 ), 2.21(t, 4H, CH 2 ), 1.88 (t, 4H, CH 2 ), 1.48 (t, 4H, CH 2 ), 1.21 (t, 4H, CH 2 ).

Embodiment 2

[0040] Embodiment two: [3] Assembly method of rotaxane system:

[0041]Weigh 48 mg (0.4 mmol) of seven-membered melon ring Q[7] and 12 mg (0.02 mmol) of guest G respectively, add them to 25ml of distilled water, and stir at 80-95°C for 2 hours. After cooling to room temperature, the aqueous solvent was removed by rotary evaporation. Precipitate with acetone, filter with suction, and dry. 55 mg of a light yellow solid was prepared with a yield of 91%. m.p.>300??C.; 1 H NMR (400 MHz, D 2 O): δ / ppm 8.35 (d, 4H, J = 6.4 Hz, ArH), 8.24 (d, 4H, J = 6.4 Hz, ArH), 7.94 (s,2H, CH=CH), 5.61 (t, 14H, J = 3.1 Hz, CH2), 5.38 (s, 14H, CH), 4.90 (d, 14H, J = 15.2 Hz, CH2), 4.10 (d, 4H, J = 15.2 Hz, CH2), 1.68 (s, 4H, CH2), 1.06 (s, 4H, CH2) , 0.85 (s, 4H, CH2), 0.45 (s, 4H, CH2).

Embodiment 3

[0042] Example 3: [3] Recognition and detection of amino acid molecules by rotaxane as a fluorescent probe

[0043] (1) Preparation method of rotaxane solution: weigh 30 mg of [3] rotaxane, dissolve in distilled water, and prepare 10 mL solution with a concentration of 1.00×10 -3 mol L -1 ;

[0044] (2) Amino acid standard solution: weigh high-grade pure lysine or arginine or a mixture of lysine and arginine to make 100mL aqueous solution, the concentration of amino acid aqueous solution is 1.00×10 -3 mol L -1 , according to the need to gradually dilute with distilled water to a suitable concentration;

[0045] Add [3] rotaxane aqueous stock solution (1.00×10 -4 mol L -1 , 1mL), amino acid aqueous solution concentration (5.00×10 -4 mol L -1 , 1 mL). Dilute to the mark with distilled aqueous solution, shake well, place at room temperature for 2 h, and transfer to a 3 cm quartz cuvette for fluorescence spectrum measurement. The excitation and emission wavelengths of...

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Abstract

The invention discloses a cucurbit [7] uril [3] rotaxane as well as a preparation method and application thereof, and belongs to the technical fields of organic synthesis and analytical chemistry. A fluorescence probe cucurbit [7] uril [3] rotaxane prepared by the method can be applied to high-selectivity and high-sensitivity detection of lysine or arginine or a mixture of the lysine and the arginine. Under the medium condition of an aqueous solution, a trace amount of lysine or arginine or the mixture of the lysine and the arginine can be detected by taking cucurbit urils supramolecular self-assembly as a probe system by adopting a fluorescence emission spectrophotometry at high sensitivity and high selectivity. The invention also discloses a preparation method and a technological condition of the cucurbit [7] uril [3] rotaxane. The reacting fluorescence excitation wavelength of the cucurbit [7] uril [3] rotaxane and the lysine or the arginine or the mixture of the lysine and the arginine is 317nm; and the maximal emission wavelength is 375nm.

Description

technical field [0001] The invention belongs to the field of organic synthesis and analytical chemistry. Specifically, it relates to a seven-membered cucurbit[3]rotaxane and its preparation method and application. Background technique [0002] Fluorescent probe technology based on molecular recognition, through the selective binding of specific target molecules and ions, the recognition information can be converted into easily detectable spectral signals through corresponding fluorescent signal transduction, so as to achieve in situ detection at the molecular level. , real-time detection, and can provide rich spectral information, and play an important role in various ion detection, DNA and protein molecular labeling, cell imaging, immune analysis, etc. [0003] Amino acids are the basic substances that make up living organisms and the basic substances of cell metabolism. The rapid identification of amino acids is of great significance to the analysis of cell metabolism, s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/22C07D213/04C09K11/06G01N21/64
CPCC07D487/22C07D213/04C09K11/06C09K2211/1029C09K2211/1044C09K2211/1074G01N21/643
Inventor 宋森倪新龙张建新陶朱
Owner GUIZHOU UNIV
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