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Fluorescent probe and preparation method thereof

A fluorescent probe and naphthalene diimide technology, applied in the field of analysis and detection, can solve the problems of high cost, low use efficiency, and difficult long-term development

Active Publication Date: 2019-09-27
SOUTH CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] To sum up, although the current several mature methods have developed relatively maturely, they all have different defects. For example, although the spectrophotometric method is simple to operate and low in cost, the accuracy is not high, and the simultaneous use of Low efficiency; although gas chromatography and liquid chromatography have excellent detection results, the operation process is complicated and the cost is high, and it is not easy to develop for a long time

Method used

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  • Fluorescent probe and preparation method thereof
  • Fluorescent probe and preparation method thereof
  • Fluorescent probe and preparation method thereof

Examples

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Embodiment 1

[0046] An embodiment of the fluorescent probe of the present invention and its preparation method, the fluorescent probe of this embodiment

[0047] It is N-n-butyl-4-(4-phenol hydroxystyryl)-1,8-naphthalene diimide, and its structural formula is as Formula (I):

[0048]

[0049] The fluorescent probe synthesis route of this embodiment is as follows figure 1 Shown, its specific preparation method is as follows:

[0050] 1) Under nitrogen protection and stirring conditions, stir and dissolve 4-bromo-1,8 naphthalene anhydride (500mg, 1.8mmol) and n-butylamine (450μL, 4.5mmol) in absolute ethanol (10-15ml) and use Heat the reaction solution to 85°C under oil bath conditions, connect the condenser to form reflux, and keep the reaction conditions for 3 to 4 hours, then stop heating. After the reaction solution is cooled to room temperature, take the reaction solution into a 250mL flask, and then use a rotary evaporator to The reaction solvent was evaporated, and the resulting ...

Embodiment 2

[0053] The action mechanism diagram of embodiment 2 fluorescent probe and isocyanate

[0054] This example tests the mechanism of action between N-n-butyl-4-(4-phenol hydroxystyryl)-1,8-naphthalene diimide fluorescent probe and isocyanate. The detection group of the fluorescent probe is a hydroxyl group, which is dissolved in an ethanol solution. After reacting with isocyanate under the condition of triethylamine, the hydroxyl group reacts to form a carbamate, and the ethanol solution of the fluorescent probe appears orange macroscopically. , the solution turns light green after interacting with isocyanate, the specific changes are as follows Figure 4 shown.

Embodiment 3

[0055] The ultraviolet fluorescence spectrum property of embodiment 3 fluorescent probes

[0056] In this example, the ultraviolet absorption and fluorescence spectra of N-n-butyl-4-(4-phenol hydroxystyryl)-1,8-naphthalene diimide fluorescent probe were tested. The specific method is as follows: Dissolve 4 mg of pure probe in 4 ml of absolute ethanol to prepare a standard probe solution (mother solution), take 300 μl into a cuvette, and then add 2.7 ml of absolute ethanol to prepare a detection solution. The detection solution is tested with a UV spectrophotometer to obtain a UV absorption spectrum as shown in Figure 5 As shown, the fluorescent probe has a strong absorption peak at 420nm; another 300 μl of the mother solution is taken into a cuvette, and then 2.7ml of absolute ethanol is added to prepare a detection solution, and the detection solution is subjected to fluorescence detection to obtain a fluorescent probe As shown in 9, the fluorescence spectrum of the fluores...

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Abstract

The invention relates to a fluorescent probe and a preparation method thereof, in particular to a ratiometric fluorescent probe for detecting isocyanate and a preparation method thereof. The structural formula of the fluorescent probe is shown as a formula (I) as shown in the description. The fluorescent probe is synthesized through multi-step molecular modification based on the fluorescent characteristic of the naphthylamide dye, and has the specific detection function on the isocyanate compound. When the fluorescent probe reacts with the isocyanate compound containing the -N=C=O group, the fluorescence emission wavelength of the product has longer blue shift than that of the probe, so that the ratiometric detection of the isocyanate compound can be achieved through the fluorescent probe. The fluorescent probe has the excellent chemical stability and the light stability, and has the high sensitivity and the specificity for detecting the isocyanate compounds.

Description

technical field [0001] The invention relates to a fluorescent probe and a preparation method thereof, in particular to a fluorescent probe for isocyanate detection and a preparation method thereof, belonging to the technical field of analysis and detection. Background technique [0002] Isocyanates are a large class of organic compounds containing (O=C=N-), including diisocyanates, monoisocyanates and polyisocyanates. Because the two heterogroup double bonds of the carbon atoms in the isocyanate group are connected to the extremely negative nitrogen and oxygen atoms, the compounds containing isocyanate groups have high chemical activity, and can be combined with most active hydrogen groups. Compounds react, such as: hydroxyl, amine, carboxyl, etc. Currently common isocyanates include toluene diisocyanate (TDI), diphenylmethane diisocyanate (MDI), isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI) and the like. [0003] Isocyanate is an important industrial ra...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): G01N21/64
CPCG01N21/6402
Inventor 侯贤锋高振忠王晓波百明阳李锰陈凯
Owner SOUTH CHINA AGRI UNIV
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