9,9'-(3,3'-dihydroxy-4,4'-diphenyl ether group) difluorone reagent and its preparation method and application

A technology of double fluorescent ketone and diphenyl ether based diformaldehyde, which is applied in chemical instruments and methods, luminescent materials, chemiluminescence/bioluminescence, etc., can solve the problems of unsatisfactory sensitivity and selectivity, and achieve stable properties and low cost. , selective effect

Inactive Publication Date: 2017-10-27
SHANXI DATONG UNIV
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Problems solved by technology

[0004] The present invention provides a 9,9'- (3,3'-dihydroxy-4,4'-diphenyl ether group) difluorone reagent and its preparation method and application

Method used

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  • 9,9'-(3,3'-dihydroxy-4,4'-diphenyl ether group) difluorone reagent and its preparation method and application
  • 9,9'-(3,3'-dihydroxy-4,4'-diphenyl ether group) difluorone reagent and its preparation method and application
  • 9,9'-(3,3'-dihydroxy-4,4'-diphenyl ether group) difluorone reagent and its preparation method and application

Examples

Experimental program
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Embodiment １

[0020] Example 1: A 9,9'-(3,3'-dihydroxy-4,4'-diphenyl ether group) difluorone reagent, referred to as 9,9'-DHDPDF, its molecular structural formula is:

[0021] .

[0022] The preparation method of the 9,9'-(3,3'-dihydroxy-4,4'-diphenyl ether group) bisfluorone reagent comprises the following steps:

[0023] (1) Synthesis of trimerol triacetate: add 28 mL of acetic anhydride and 1 mL of concentrated H to a 100 mL beaker 2 SO 4 Stir and mix, add 11g of p-benzoquinone under vigorous stirring, react at 40°C-50°C for 1.5h, pour it into 100 mL of cold water under stirring, precipitate a white precipitate, obtain 22 g of crude product by suction filtration, and recrystallize from ethanol to obtain pure product Triphenol triacetate 20 g;

[0024] (2) Preparation of 3,3'-dihydroxy-4,4'-diphenyl ether dicarbaldehyde: Add 10.1g (50 mmol) 3,3'-dihydroxydicarboxylate into a 250mL flask equipped with a reflux condenser Phenyl ether, 120 mL absolute ethanol, 28 g (0.7 mol) sodium hyd...

experiment example １

[0026] Experimental example 1: 9,9'-(3,3'-dihydroxy-4,4'-diphenyl ether group) difluorone on Co 2+ photometric analysis.

[0027] Accurately pipette ≤20 μg of Co 2+ In a 25 mL volumetric flask, add 2.0 mL of borax-sodium hydroxide buffer solution with pH 9.0, 10 g / L cetylpyridinium bromide (CPB) microemulsion (CPB: n-butanol: n-heptane : water = 1.0: 1.0: 1.0: 97) 3.0 mL, 0.2 g / L 9,9'-DHDPDF 1.0 mL, then dilute to the mark with twice distilled water, shake well and let stand for 10 min, use a 1 cm cuvette , At 660 nm, the absorbance of the complex was measured with a reagent blank as a reference.

[0028] Sample analysis: according to the literature [Journal of Pharmaceutical Analysis, 1997, Vol. 77, No. 4, 261-264. Wei Qin, Du Bin, Zhang Xuzhen], pipette vitamin B 12 Put 1.0 mL of the sample in a 50 mL beaker, add 8 mol / L nitric acid for nitration, add 5 mL of 2% hydrogen peroxide and evaporate to near dryness, add 3 mL of 1∶1 hydrochloric acid and appropriate amount of wa...

experiment example ２

[0035] Experimental example 2: Determination of nickel by 9,9'-(3,3'-dihydroxy-4,4'-diphenyl ether group) bisfluorone fluorescence quenching method.

[0036] Accurately weigh ≤0.005µg nickel in a 25ml volumetric flask, add 2 mL of 3 % Tritonx-100 aqueous solution, 3.0 mL of borax-hydrochloric acid buffer solution with pH 9.4, 2×10 -5 mol / L 9,9'-DHDPDF ethanol solution 2.0 mL, dilute to volume with water, and place for 10 min. Using a 1cm quartz cuvette, at the excitation wavelength (λ ex )465 nm, emission wavelength (λ em ) at 586 nm to measure the fluorescence intensity F of the complex, and at the same time measure the fluorescence absorbance F of the reagent blank under this condition, and calculate the fluorescence quenching value ΔF (ΔF=F 0 -F).

[0037] Sample determination: Weigh 1.0000 g of solid sample, carry out microwave digestion on the sample according to the literature [Food Science, 2011, Vol. Volume 2, pp. 158-160, Wei Qin] separated and enriched nickel, an...

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Abstract

The invention belongs to the technical field of phenylfluorone compounds and provides a 9,9'-(3,3'-dihydroxy-4,4'-diphenylether)bifluorone reagent and a preparation method and application thereof to solve the problem that an existing phenylfluorone compound having non-ideal sensitivity and selectivity is unable to serve as a fluorescent reagent in the fluorescent detection of metal ions.Two pyranoid ring structural units are introduced in molecules, the quantity of metal ion coordination sites is increased by one time, the ability of the reagent to coordinate with metal ions is enhanced, and the fluorescent reagent good in sensitivity and selectivity is obtained.The preparation method is simple, the cost is low, properties are stable, a detection limit in nickel determination by fluorophotometric quenching process in a basic medium in the presence of a surfactant is lower that of other reagent quenching processes, cobalt determination by spectrophotometry is higher than other fluorone reagent processes in sensitivity, and a detection limit in cobalt determination by discoloring spectrophotometry is lower than that of a process using other fluorone reagents.This reagent has high detection speed for nickel and cobalt ions and is good in selectivity, high in sensitivity and high in complex stability.

Description

technical field [0001] The invention belongs to the technical field of phenylfluorone compounds, and specifically relates to a 9,9'-(3,3'-dihydroxy-4,4'-diphenyl ether group) difluorone reagent and its preparation method and application . Background technique [0002] Fluorone reagents refer to a class of triphenylmethane derivatives containing 2,3,7-trihydroxy-6-keto-pyran ring structure in the molecule. The compound formed when the 9-position hydrogen atom is replaced by phenyl is also known as phenylfluorone (see structure figure 1 ). Phenylfluorone is mostly orange or red crystals, hardly soluble in water and cold ethanol, but easily soluble in acidified ethanol. Molecules of such compounds are rigid, planar conjugation and large Bond structure, easy to absorb ultraviolet-visible light and excited to produce fluorescence. Its color reaction functional group is the o-dihydroxy group or o-hydroxyquinone group at both ends of the molecule. Oxygen atoms in hydroxyl an...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/82C09K11/06G01N21/76
CPCC07D311/82C09K11/06C09K2211/1088G01N21/76
Inventor 刘慧君樊月琴赵强马琦樊志会宋金萍
Owner SHANXI DATONG UNIV
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