Fluorescence sensing film based on boron dipyrromethene-phenyl boronic acid (BODIPY-PBA), preparation method and application thereof

A technology of fluoroboron dipyrrole and fluorescent sensing membrane, which is applied in the field of probes to achieve the effect of fast response time and good selectivity

Active Publication Date: 2012-10-17
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

There are few reports on the use of boronic acid dye-based lipophilic polymer sensing membranes for the detection of carbohydrates 17 , although such membranes are widely used to extract carbohydrates from aqueous solutions 18

Method used

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  • Fluorescence sensing film based on boron dipyrromethene-phenyl boronic acid (BODIPY-PBA), preparation method and application thereof
  • Fluorescence sensing film based on boron dipyrromethene-phenyl boronic acid (BODIPY-PBA), preparation method and application thereof
  • Fluorescence sensing film based on boron dipyrromethene-phenyl boronic acid (BODIPY-PBA), preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Example 1: Synthesis of BODIPY-PBA derivatives.

[0044] 1. Fluoroboron dipyrrole-phenylboronic acid is 8-phenylboronic acid pinacol ester-1,3,5,7-tetramethyl-4,4-difluoro-4-boron-3a,4a-diazepine symmetry Indacene (compound 2a) and 8-phenylboronic acid-1,3,5,7-tetramethyl-4,4-difluoro-4-boron-3a,4a-diazasymmetric indacene (compound 2b )Synthesis.

[0045] 13g (70mmol) of p-bromobenzaldehyde and 16ml (2.1eq) of 2,4-dimethylpyrrole and 50ml of dichloromethane were stirred under the protection of nitrogen under an ice-water bath. Trifluoroacetic acid was added dropwise, and the temperature was naturally raised to room temperature after the drop, and reacted in the dark for 6 hours. Add 16g (70mmol) dichlorodicyanobenzoquinone (DDQ) to continue the reaction for 2 hours, add dropwise N,N-isopropylethylamine (DIPEA) 90mL (7.0eq) and 100mL (7.0eq) boron trifluoride ether , Protected from light and reacted for 4h, the reaction mixture was washed with water, dried, and the so...

Embodiment 2

[0056] Example 2: Homogeneous detection.

[0057] Dissolve 1 μM compounds 2a, 2b, and 4b in ethanol, respectively, for the detection of optical properties, such as figure 2 shown. The emission wavelengths of 2a, 2b, and 4b are 510nm, 522nm, and 580nm, respectively. 2b was mixed with equal volumes of buffer solutions with different pH values ​​to prepare 1 μM BODIPY-PBA for pH response detection, image 3 is the response of the 2b probe to pH, and the fluorescence intensity increases with the increase of alkalinity. The pKa of 2b is 10.1, which is higher than that of phenylboronic acid, mainly due to the influence of the structure of BODIPY 24 . In the BODIPY-PBA structure, since the BODIPY fluorophore and the intermediate substituted phenylboronic acid are perpendicular to each other, the two parts are separated. The trisubstituted boron atom is sp 2 The hybrid planar triangular structure, with empty p orbitals, enables boronic acid to accept electrons. It is obvious t...

Embodiment 3

[0060] Example 3: Preparation and detection of polymer optical sensor.

[0061] A fluorescent sensing film based on fluoroborate dipyrrole-phenylboronic acid, which includes the following components in weight percentage:

[0062]

[0063] The BODIPY-PBA selects compounds 2a, 2b or 4b, respectively.

[0064] The preparation method of the above-mentioned fluorescent sensing film based on fluoroboridipyrrole-phenylboronic acid: the formulation amount of fluoroboridipyrrole-phenylboronic acid, tridodecylmethylammonium chloride, polyvinyl chloride and 2-nitrobenzene Mix with n-octyl ether, dissolve in an organic solvent, mix thoroughly, apply a film evenly on the substrate, and dry it at room temperature to avoid light. The organic solvent is tetrahydrofuran (THF) or dimethylsulfoxide (DMSO). Wherein, the ratio of the added volume of the organic solvent to the total weight of fluoroborate dipyrrole-phenylboronic acid, tridodecylmethylammonium chloride, polyvinyl chloride and 2...

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Abstract

The present invention discloses a fluorescence sensing film based on boron dipyrromethene-phenyl boronic acid (BODIPY-PBA), wherein the fluorescence sensing film comprises, by weight, 0.18% of BODIPY-PBA, 0.14% of tridodecyl methyl ammonium chloride, 33.23% of polyvinyl chloride, and the balance of 2-nitrophenyl octyl ether. The present invention further discloses a preparation method for the fluorescence sensing film based on the BODIPY-PBA, and an application of the fluorescence sensing film. According to the present invention, the new synthesis route is adopted to prepare a series of BODIPY-PBA derivatives, wherein the BODIPY-PBA derivatives have different emission wavelengths and high quantum yields. With application of the BODIPY-PBA in fluorescent probes, monosaccharide can be detected in homogeneous phases and polymer optical sensing films, the fructose selectivity is particularly good, the response time is short (20 minutes), and the glycogen can be directly detected in homogeneous phases.

Description

technical field [0001] The invention belongs to the technical field of probes, and in particular relates to a fluorescent sensing film based on fluoroborate-dipyrrole-phenylboronic acid and a preparation method and application thereof. Background technique [0002] Sugars, including monosaccharides, disaccharides, oligosaccharides and polysaccharides, are an important part of life and the main source of energy, so the detection of sugars is of great significance in the fields of medical diagnosis, food technology and biological science 1-3 . One of the earliest methods for detecting sugars was the enzyme electrode developed in the 1960s. 4 . In addition, chemical sensors with fluorescent dyes and chelating groups are attracting more and more attention. 5，6 . Especially acceptors with boronic acid have been used in sugar sensors, because the neutral structure of boronic acid is sp 2 Hybrid, planar triangular structure, electron-deficient Lewis acid can quickly and revers...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): G01N21/64C07F5/02C07F5/04
Inventor 秦玉翟晶莹潘婷
Owner NANJING UNIV
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