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9, 9'-(N-phenyl-N, N-4, 4'-diphenyl) double fluorescein reagent and preparation method and application thereof

A dual-fluorescein and diphenyl technology, which is applied in the directions of fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of unsatisfactory sensitivity and selectivity of reagents for detecting heavy metal ions, and achieve a simple preparation method and low cost. Effect

Inactive Publication Date: 2017-06-13
SHANXI DATONG UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The present invention aims to provide a preparation method and application of a 9,9'-(N-phenyl-N,N-4,4'-diphenyl)bisfluorone reagent to solve the problem of detecting heavy metal ions in the prior art The sensitivity and selectivity of reagents are not ideal enough. Triphenylamine, which has a large degree of conjugation and fluorescence characteristics, is prepared by formylation reaction to 4,4'-diformyl triphenylamine, and then combined with trimeryltriphenol triacetic acid 9,9'-(N-phenyl-N,N-4,4'-diphenyl)bifluorone reagent (abbreviated as 9,9'-NNBPBF) with high sensitivity and good selectivity for ester reaction synthesis

Method used

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  • 9, 9'-(N-phenyl-N, N-4, 4'-diphenyl) double fluorescein reagent and preparation method and application thereof
  • 9, 9'-(N-phenyl-N, N-4, 4'-diphenyl) double fluorescein reagent and preparation method and application thereof
  • 9, 9'-(N-phenyl-N, N-4, 4'-diphenyl) double fluorescein reagent and preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0032] Example 1: A preparation method of 9,9'-(N-phenyl-N,N-4,4'-diphenyl)bisfluorone

[0033] The reaction formula is as follows:

[0034]

[0035] A method for preparing 9,9'-(N-phenyl-N,N-4,4'-diphenyl)bisfluorone, comprising the following steps:

[0036] (1) Synthesis of p-benzoquinone

[0037] Dissolve 20.0g of hydroquinone in a 1000mL long-necked flask filled with 333mL of 50°C hot water, and then slowly add 20mL of concentrated H 2 SO 4 , use crushed ice to strictly control the reaction temperature at 20-30°C, then slowly add 266.6mL K 2 Cr 2 o 7 solution (contains K 2 Cr 2 o 7 32.79g). After the reaction, the crude product of p-benzoquinone was obtained by suction filtration, washed with cold water and dried to obtain 9.5 g of yellow p-benzoquinone with a yield of 48.3%.

[0038] (2) Synthesis of trimerol triacetate

[0039]In a 100 mL round bottom flask, add 40.0 mL of acetic anhydride and 2.0 mL of concentrated sulfuric acid in sequence, and add 9.5 g...

Embodiment 2

[0049] Example 2: 9,9'-(N-phenyl-N,N-4,4'-diphenyl)bifluorone reagent spectrophotometry on Zn 2+ Analysis and detection of ions

[0050] In a 25mL volumetric flask, accurately pipette no more than 15μg of Zn 2+ , followed by adding 2.0mL of borax-NaOH buffer solution with pH 10.6, 1.5mL of CPB (cetylpyridinium bromide)-OP microemulsion (CPB:OP:n-butanol:n-heptane:H 2 The mass ratio of O is 1:5:3.5:0.8:89), 2.0mL 0.3g / L 9,9'-NNBPBF ethanol solution, then dilute to the mark with twice distilled water, shake well and let it stand for 15min, then use 1cm ratio The color dish is at 620nm, and the absorbance of the system is measured with the reagent blank as a reference.

[0051] According to the literature [Analytical Chemistry, Wei Qin et al., 2004, Vol. 32, No. 11, No. 1509-1512], accurately weigh 5 g of the sample, place it in a muffle furnace and incinerate at 600 °C for 4 h, add a small amount of hydrochloric acid (1+1) to dissolve the residue, and then add 4 mL Nitric aci...

Embodiment 3

[0056] Example 3: 9,9'-(N-phenyl-N,N-4,4'-diphenyl)bifluorone reagent fluorescence quenching method on Cu 2+ Analysis and detection of ions

[0057] In a 25mL volumetric flask, add no more than 5μg of Cu 2+ , add 2.0mL 1.0×10 -4 mol / L 9,9'-NNBPBF ethanol solution, 3.0 mL pH=8.0 triethanolamine-hydrochloric acid buffer solution, 3.0 mL absolute ethanol, 4.0 mL 0.5% cetyltrimethylammonium bromide (CTMAB) Solution, then diluted with water to the mark, shake well. Prepare the reagent blank in the same way. Leave it for 10min. on a spectrofluorometer at λ ex =556nm,λ em = Measure the fluorescence intensity F, F of the test solution and the blank at 596nm 0 , calculate the fluorescence quenching value ΔF=F 0 -F.

[0058] According to the literature [Analytical Chemistry, 2004,32(6):838], accurately weigh 1g of clean hair sample in a small beaker, add 10mL HNO 3 , digested by heating at low temperature until the brown gas escapes, and the solution is light yellow, add 1mL H...

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Abstract

The invention discloses 9,9'-(N-phenyl-N,N-4,4'-diphenyl)bifluorone. According to the invention, triphenylamine with a great conjugation degree and fluorescence characteristics is subjected to formylation so as to prepare 4,4'-diformyl triphenylamine, and 4,4'-diformyl triphenylamine reacts with hydroxyquinol triacetate so as to synthesize a 9,9'-(N-phenyl-N,N-4,4'-diphenyl)bifluorone reagent (9,9'-NNBPBF, for short) with high sensitivity and good selectivity. The reagent can be used for spectrophotometric detection of Zn<2+> in an alkaline medium and fluorescence quenching detection of Cu<2+>.

Description

technical field [0001] The invention belongs to the technical field of fluorone compounds, and in particular relates to a preparation method and application of a 9,9'-(N-phenyl-N,N-4,4'-diphenyl)bisfluorone reagent. Background technique [0002] Phenylfluorone reagents are a class of acidic triphenylmethane organic dye reagents, mostly red solids, insoluble in water, easily soluble in acidified ethanol, and the solubility and Sensitivity of color reaction with metal ions. This type of reagent is a rigid planar macromolecular reagent with a conjugated large π bond, so it has strong fluorescence properties. In addition, because there are 3 hydroxyl groups at the 2, 3 and 7 positions of the pyran ring, the oxygen atom in the hydroxyl group has Two lone pairs of electrons, or the hydroxyl group is easy to form oxygen negative ions in alkaline medium, which can form coordination bonds with empty orbitals of metal ions [Huang Yingping, Zhang Huali. Metallurgical Analysis, 1977.17...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/90C09K11/06G01N21/64
CPCC07D311/90C09K11/06C09K2211/1022C09K2211/1088G01N21/643G01N2021/6432
Inventor 吕存琴刘建红郭永晋春费鹏张进
Owner SHANXI DATONG UNIV
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