Perylene diimide derivative, preparation method and application of perylene diimide derivative in preparation of ATP (adenosine triphosphate) fluorescent probe

A technology of perylene imide and fluorescent probe, applied in the field of fluorescent probe, can solve the problems of poor solubility of perylene imide derivatives, harsh synthesis conditions, high reaction temperature, etc. good effect

Active Publication Date: 2020-02-04
TIANJIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] However, due to the influence of special structure, the solubility of most perylene imide derivatives is relatively poor, and the synthesis conditions are relatively harsh, usually requiring higher reaction temperature, longer reaction time and special reaction solvents, etc., which limit the The application of such materials in some aspects

Method used

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  • Perylene diimide derivative, preparation method and application of perylene diimide derivative in preparation of ATP (adenosine triphosphate) fluorescent probe
  • Perylene diimide derivative, preparation method and application of perylene diimide derivative in preparation of ATP (adenosine triphosphate) fluorescent probe
  • Perylene diimide derivative, preparation method and application of perylene diimide derivative in preparation of ATP (adenosine triphosphate) fluorescent probe

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Experimental program
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Effect test

Embodiment 1

[0039] A preparation method of perylene imide derivatives, comprising the steps of:

[0040](1) Weigh 1.00g (2.55mmol) 3,4,9,10-perylenetetracarboxylic dianhydride (I), 1.15g (6.37mmol) 5-aminoisophthalic acid, 0.200g (0.912mmol) Zinc acetate in water and 20g imidazole were placed in a round bottom flask, heated to 127°C and stirred for 6 hours under nitrogen protection; after the reaction was completed, transferred to a container with a reflux device, and 100mL of absolute ethanol was added, refluxed 6 hours; stop heating and stirring, leave standstill 10h; Vacuum suction filtration obtains dark red precipitate, and washes repeatedly 3 times with absolute ethanol, obtains compound (II), and the productive rate is 83.2%, and its structure is passed by nuclear magnetic spectrum and Infrared for confirmation; hydrogen spectrum: δ (TMS, ppm): 7.15 (m, 8H), 8.11 (s, 4H), 8.43 (s, 2H); infrared (KBr, cm -1 ):1698,1664,1596,1353,1251;

[0041] (2) Weigh 33.7mg (0.6mmol) of potassi...

Embodiment 2

[0050] A kind of purposes that perylene imide derivative prepares ATP fluorescent probe, comprises the steps:

[0051] Put the peryleneimide derivative (IV) prepared in Example 1 into an aqueous ethanol solution with a volume concentration of 50%, shake it, and prepare a kind of ATP fluorescent probe; the peryleneimide derivative (IV) and ethanol The molar ratio is 1:12500.

Embodiment 3

[0053] The measurement of the optical properties of the ATP fluorescent probe prepared in embodiment 2 under different ATP concentrations

[0054] Get 9 parts of ATP fluorescent probe solution (I) that the volume is 5mL prepared by Example 2, then add respectively 5mL containing 0, 0.4, 0.8, 1.2, 1.6, 2, 2.4, 2.8, 3 equivalents The ethanol aqueous solution of the ATP (the ethanol aqueous solution volume concentration is 50%), measure its ultraviolet-absorption spectrum and fluorescence spectrum, see figure 2 and image 3 . From figure 2 It can be seen from the UV-absorption spectrum that without adding ATP, the maximum absorption wavelength is around 529nm, and there are two peaks around 492nm and 460nm. With the gradual addition of ATP, the peaks at 529 and 492nm decreased gradually, while the absorption peak at 460nm increased gradually, a new peak appeared at 577nm, and a clear isosbestic point appeared at 548nm. exist image 3 It can be seen from the fluorescence sp...

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Abstract

The invention discloses a perylene diimide derivative, a preparation method and application of the perylene diimide derivative in preparation of an ATP (adenosine triphosphate) fluorescent probe. Theperylene diimide derivative is shown as a formula (IV), wherein R<+> = R'2(CH3)2N<+>, and R' is linear alkyl with 16-18 carbon atoms, branched alkyl or alkyl with a cyclic alkyl chain. The ATP fluorescent probe prepared from the perylene diimide derivative can selectively and quickly detect ATP, the prepared ATP fluorescent probe is good in chemical stability, high in sensitivity and good in selectivity and can be combined with a commercial fluorescent instrument to achieve quick response and real-time monitoring of the ATP; the perylene diimide derivative is used for preparing the fluorescentprobe high in luminescence performance and capable of quickly selectively analyzing the ATP, the preparation method is simple and convenient, reaction conditions are mild, reaction is performed in ethanol water, environment pollution is avoided, the requirements of green chemical probes are met, synthesis is simple, and products are easy to separate and purify.

Description

technical field [0001] The invention belongs to the technical field of fluorescent probes, and in particular relates to a perylene imide derivative, a preparation method and an application for preparing an ATP fluorescent probe. Background technique [0002] Perylene diimide (PDI) derivatives are an important class of fused-ring aromatic hydrocarbon compounds. This type of compound has a large conjugated system, high fluorescence quantum yield, and a wide range of absorption spectra. Excellent photoelectric properties and thermal stability. Since it was first synthesized in the 10s of the 20th century, after more than 100 years of development, it has played a very important role in the fields of organic light-emitting diodes, liquid crystal display materials, molecular switches, photovoltaic devices and fluorescent probes, and has important application value. . [0003] However, due to the influence of special structure, the solubility of most perylene imide derivatives is...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/06C09K11/06G01N21/64
CPCC07D471/06C09K11/06G01N21/643C09K2211/1007C09K2211/1029
Inventor 任相魁曾雨婷刘婕郭锦棠冯亚凯
Owner TIANJIN UNIV
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