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CN-122010997-A - Amino-bridged tetraphenyl ethylene phenylborate compound, synthesis method and application thereof, and glucose fluorescence detection method

CN122010997ACN 122010997 ACN122010997 ACN 122010997ACN-122010997-A

Abstract

The invention relates to the technical field of biological micromolecule fluorescence detection, and discloses an amino bridged tetraphenyl ethylene phenylborate compound, a synthesis method and application thereof and a glucose fluorescence detection method, wherein the compound takes tetraphenyl ethylene as an aggregation-induced emission parent nucleus, and can be specifically combined with glucose to generate an aggregation-induced emission effect through quaternized amino bridged biphenyl boric acid recognition groups; the invention also provides a two-step synthesis method of the compound, which has the advantages of simple synthesis route, mild condition, stable product purity and yield, and the glucose detection method constructed based on the compound avoids the inherent defects of the traditional enzymatic detection, improves the water solubility and glucose binding kinetics performance of the sensing molecule, has the advantages of high detection sensitivity, wide linear range, simple and convenient operation and strong anti-interference capability, and is suitable for the rapid quantitative detection of glucose in an aqueous phase system.

Inventors

  • ZHU QIJIAN
  • ZHONG TINGTING
  • JI QING
  • CHEN LONG

Assignees

  • 茅台学院

Dates

Publication Date
20260512
Application Date
20260325

Claims (10)

  1. 1. An amino-bridged tetraphenyl vinyl phenyl borate compound is characterized by having the following structural formula: 。
  2. 2. a method for synthesizing an amino-bridged tetraphenyl vinyl phenyl borate compound according to claim 1, comprising the steps of: (1) Synthesizing para-dimethylamino substituted tetraphenyl ethylene by using 1-bromo-1, 2-triphenylethylene and 4- (N, N-dimethylamino) phenylboronic acid as raw materials and performing Suzuki coupling reaction under the action of a palladium catalyst to obtain para-dimethylamino substituted tetraphenyl ethylene; (2) And (3) synthesizing a target compound, namely dissolving 4-bromomethyl phenyl borate and the p-dimethylamino substituted tetraphenyl ethylene prepared in the step (1) in anhydrous acetonitrile under the protection of inert gas, stirring at room temperature for reaction, distilling under reduced pressure to remove a solvent, and purifying by column chromatography to obtain the target amino bridged tetraphenyl vinyl phenyl borate compound.
  3. 3. The synthesis method according to claim 2, wherein the palladium catalyst in the step (1) is tetrakis (triphenylphosphine) palladium, the reaction solvent is a mixed system of tetrahydrofuran and aqueous potassium carbonate, the reaction mode is reflux reaction overnight, the product is purified by silica gel column chromatography, and the eluent is a mixed solution of dichloromethane and petroleum ether in a volume ratio of 1:6.
  4. 4. The method of claim 2, wherein the inert gas in the step (2) is argon, the reaction time is 12-24 hours, and the eluent for column chromatography purification is a mixture of ethyl acetate and petroleum ether in a volume ratio of 1:10.
  5. 5. Use of the amino-bridged tetraphenyl ethylene phenylboronate compound of claim 1 in the fluorescent detection of glucose.
  6. 6. A glucose fluorescence detection method is characterized in that the amino-bridged tetraphenyl ethylene phenylborate compound as defined in claim 1 is adopted as a fluorescence sensing molecule, and the method comprises the following steps: (1) Preparing a detection solution containing the fluorescent sensing molecules, wherein the solvent of the detection solution is a mixed solvent of dimethyl sulfoxide and water; (2) Mixing the glucose sample solution to be detected with the detection solution in an equal volume, and standing to obtain a sample to be detected; (3) And (3) carrying out fluorescence spectrum acquisition on the sample to be detected by adopting a fluorescence spectrophotometer, and realizing quantitative detection of glucose according to the fluorescence intensity of the characteristic emission peak.
  7. 7. The method of fluorescence detection of glucose according to claim 6, wherein the volume ratio of dimethyl sulfoxide to water in the mixed solvent is 1:10 to 1:30.
  8. 8. The method of fluorescence detection of glucose according to claim 6, wherein the pH of the detection solution is adjusted to 10.0 to 11.0 by using a potassium carbonate-potassium bicarbonate buffer system, and the concentration of the fluorescent sensor molecule in the detection solution is 0.005mM to 0.02mM.
  9. 9. The method of fluorescence detection of glucose according to claim 6, wherein the time of the standing treatment in the step (2) is not less than 12 hours, the excitation wavelength for fluorescence spectrum collection in the step (3) is 310nm, the emission spectrum collection range is 320nm to 700nm, and the excitation slit width and the emission slit width are both 5nm.
  10. 10. The method of claim 6, wherein the fluorescent peak intensity at 500nm is used as a quantitative basis in the step (3), a linear standard curve of the fluorescent intensity and the glucose concentration is established in advance, and the glucose concentration is obtained by calculating the fluorescent intensity of the sample to be measured.

Description

Amino-bridged tetraphenyl ethylene phenylborate compound, synthesis method and application thereof, and glucose fluorescence detection method Technical Field The invention relates to the technical field of biological small molecule fluorescence detection, in particular to an amino bridged tetraphenyl ethylene phenylborate compound, a synthesis method and application thereof, and a glucose fluorescence detection method. Background Glucose is a core energy substance necessary for a living body to maintain normal physiological operation, and its content level in the living body is closely related to the metabolic state of the body. In recent years, with the improvement of living standards of residents and the diversification of dietary structures, daily sugar intake of people is remarkably increased, and long-term overload sugar intake can cause various metabolic diseases such as obesity, diabetes and the like, and the incidence of the diseases is in a situation of rising year by year and becoming younger. Therefore, the development of a simple, rapid and high-sensitivity glucose detection method has very important practical significance for early screening, daily monitoring and clinical diagnosis of metabolic diseases. In the existing glucose detection technology, the fluorescence detection method has been widely studied and applied by virtue of the advantages of high response speed, high detection sensitivity, portability in operation, capability of realizing in-situ detection and the like. Currently, the mainstream fluorescence method glucose detection is realized by a catalytic system based on glucose oxidase, the method relies on the catalytic activity of biological enzyme, and the biological enzyme has the defects of poor stability, complex preparation process and severe storage and use conditions, is extremely easy to be inactivated due to the influence of factors such as environmental temperature, pH and the like, is difficult to meet the requirements of on-site rapid detection and long-term stable use, and limits the expansion of application scenes. In view of the inherent defects of enzymatic detection, non-enzymatic fluorescent glucose detection technology has become a recent research focus. The prior reported non-enzymatic fluorescence detection technology is constructed based on a photoinduced electron transfer mechanism, however, the rationality of the detection mechanism is always in question in the industry, and researchers are provided with phenylboronic acid sensors constructed based on anthracene fluorophores, so that the fluorescence response of the phenylboronic acid sensors to glucose is proved to be derived from the depolymerization process of fluorescent molecule aggregates, but not the photoinduced electron transfer effect which is recognized before. In addition, researchers construct an aggregation-induced emission type glucose sensor based on tetraphenyl ethylene phenylboronic acid, which forms a dimer through bonding of glucose and a sensing molecule and inhibits benzene ring rotation to improve fluorescence intensity, so that the detection of glucose is realized, but the sensing molecule has poor water solubility, has insufficient binding kinetics performance on glucose in an aqueous phase system, has a detection effect limited by the number of molecules bound, lacks a simple, convenient, efficient and large-scale preparation synthetic route, and is difficult to realize high-sensitivity and wide-range quantitative detection and industrialization application of glucose. Disclosure of Invention The invention aims to provide an amino-bridged tetraphenyl vinyl phenyl borate compound, a synthesis method, application and a glucose fluorescence detection method thereof, so as to solve the technical problems that in the existing glucose fluorescence detection technology, enzyme method relies on biological enzyme to have inherent defects of poor stability, complex preparation and harsh use conditions, but the enzyme aggregation-induced emission sensor molecule has poor water solubility, insufficient glucose binding kinetics, the detection effect is limited by the number of molecules bound, and a simple and large-scale preparation synthetic route is lacking. In order to achieve the aim, the invention adopts the following technical scheme that an amino bridged tetraphenyl ethylene phenylborate compound has the following structural formula: 。 the synthesis method of the amino-bridged tetraphenyl ethylene phenylborate compound comprises the following steps: (1) Synthesizing para-dimethylamino substituted tetraphenyl ethylene by using 1-bromo-1, 2-triphenylethylene and 4- (N, N-dimethylamino) phenylboronic acid as raw materials and performing Suzuki coupling reaction under the action of a palladium catalyst to obtain para-dimethylamino substituted tetraphenyl ethylene; (2) And (3) synthesizing a target compound, namely dissolving 4-bromomethyl phenyl borate and the p-dimethylamino substituted te