Naphthylthiourea-modified permethylated beta-cyclodextrin derivative, preparation method and application method thereof

A technology of naphthyl thiourea and methylation, applied in fluorescence/phosphorescence, material excitation analysis, etc., can solve the problems of complex synthetic routes, low sensitivity, and long response time, and achieve simple synthetic routes, good sensitivity, and selectivity sex high effect

Inactive Publication Date: 2010-02-10
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, many of the above-mentioned methods for identifying mercury have complex synthetic routes; low yield; poor water solubility, need to add auxiliary organic solvents; long response time; or low sensitivity and so on. Cyclodextrin has good water solubility, but there are few reports on the use of cyclodextrin-modified derivatives for mercury ion recognition

Method used

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  • Naphthylthiourea-modified permethylated beta-cyclodextrin derivative, preparation method and application method thereof
  • Naphthylthiourea-modified permethylated beta-cyclodextrin derivative, preparation method and application method thereof
  • Naphthylthiourea-modified permethylated beta-cyclodextrin derivative, preparation method and application method thereof

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Experimental program
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Effect test

Embodiment 1

[0036] Synthesis of permethylated β-cyclodextrin derivatives modified by naphthylthiourea

[0037] Synthetic route such as figure 2

[0038] The synthesis steps are as follows:

[0039] Under a nitrogen atmosphere, 1.0 mmol 6-deoxy-6-amino-permethylated-β-cyclodextrin and 3.0 mmol 1-naphthyl isothiocyanate were reacted in a dry dichloromethane solution under electromagnetic stirring at room temperature After 24 hours, the solvent was removed by rotary evaporation. The obtained solid was separated with a silica gel column. The eluent was ethyl acetate to obtain a white naphthylthiourea modified permethylated β-cyclodextrin derivative with a yield of 85% and a molecular weight It is 1598.7g / mol.

Embodiment 2

[0041] Synthesis of permethylated β-cyclodextrin derivatives modified by naphthylthiourea

[0042] Synthetic route such as figure 2

[0043] The synthesis steps are as follows:

[0044] Under a nitrogen atmosphere, 1.0 mmol 6-deoxy-6-amino-permethylated-β-cyclodextrin and 30.0 mmol 1-naphthyl isothiocyanate were reacted in a dry dichloromethane solution under electromagnetic stirring at room temperature After 24 hours, the solvent was removed by rotary evaporation. The obtained solid was separated with a silica gel column. The eluent was ethyl acetate to obtain a white naphthylthiourea modified permethylated-β-cyclodextrin derivative with a yield of 86%. The molecular weight is 1598.7g / mol.

Embodiment 3

[0046] Compound characterization

[0047] The NMR, elemental analysis and mass spectrometric characterization of the naphthylthiourea modified permethylated β-cyclodextrin derivative of the present invention:

[0048] 1 HNMR(400MHz, D 2 O, ppm), δ3.06-3.66 (m, 101H, H of C-3, C-5, C-6, C-2, C-4, OC), 5.06-5.34 (m, 7H, H of C-1), 7.58-7.60 (m, 4H, H of naphthalene), 7.92-7.99 (m, 3H, H of naphthalene). C 73 H 118 N 2 O 34 S: Measured value: C, 54.50%; H, 7.76%; N, 1.72%. Theoretical value: C, 54.81%; H, 7.43%; N, 1.75%. ESI-MS: 1599.6[M+H] + , 1621.7[M+Na] + .

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Abstract

The invention discloses a naphthylthiourea-modified permethylated beta-cyclodextrin derivative, a preparation method and an application method thereof, the chemical formula of the compound is C73H118N2O34S, and the structure and the schematic diagram are shown as attached figures. The compound is simply prepared by the reaction of an amino derivative of cyclodextrin and naphthalene isothiocyanatewith high yield. The compound has high selectivity and high sensitivity on the recognition of mercury ions due to high sulphophile affinity of mercury. The divalent mercury ions are added in the compound in a water phase, fluorescence can be greatly ascended in a short period of time, the detection limit is 50ppb, the compound is resistant to the addition of other ions, such as, Li<+>, Na<+>, K<+>, Mg<2+>, Ca<2+>, Sr<2+>, Ba<2+>, Ag<+>, Cd<2+>, Ce<2+>, Co<2+>, Cu<2+>, Ni<2+>, Pb<2+>, Sr<2+>, Zn<2+> and the like, and the compound has no obvious change after the addition of other ions. The invention provides a reagent and a method which can rapidly test water solubility of the mercury ions in an environment and a biological body with high selectivity, high sensitivity and fluorescence enhancement and is applicable to the wider pH range of (3-12).

Description

【Technical Field】: [0001] The invention belongs to the field of material chemistry and applied chemistry, and relates to a naphthylthiourea modified permethylated β-cyclodextrin derivative, and a preparation method and application thereof in a wide pH (3-12) application range in an aqueous phase To divalent mercury ion (Hg 2+ ) Highly selective and rapid identification method and fluorescence sensing mechanism. 【Background technique】: [0002] Mercury is an element with great physiological toxicity. Because of its high bioaccumulation and its wide use in industry, its toxicity has attracted worldwide attention. The divalent mercury ion in the form of inorganic salt is considered to be one of the most dangerous and toxic inorganic metal ions, because it can be converted into more toxic methylmercury by microorganisms in water and can damage the human center through bioaccumulation The nervous system, and the detection of divalent mercury ions has become a major topic of common co...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08B37/16G01N21/64
Inventor 刘育孙战虎陈湧王克让蒋邦平
Owner NANKAI UNIV
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