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Perylene imide derivative, preparation method and application of preparing atp fluorescent probe
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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: 2022-05-10
TIANJIN UNIV
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[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
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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 imide derivative and its preparation method and the use of preparing ATP fluorescent probe. The perylene imide derivative is represented by formula (IV): wherein: R + =R' 2 (CH 3 ) 2 N + ; R' is a straight-chain alkyl group, a branched-chain alkyl group or an alkyl group with a cyclic alkyl chain having 16-18 carbon atoms. (1) The peryleneimide derivative ATP fluorescent probe of the present invention can detect ATP selectively and rapidly, and the prepared ATP fluorescent probe has good chemical stability, high sensitivity and good selectivity. The combined use of needles and commercial fluorescence instruments can realize rapid response and real-time monitoring of ATP; (2) the perylene imide derivatives of the present invention prepare fluorescent probes with high luminescence performance and rapid selective analysis of ATP, and the preparation method is simple and convenient. The reaction condition is mild, carried out under the condition of ethanol aqueous solution, has no pollution to the environment, meets the characteristics of a green chemical probe, and is simple in synthesis, and the product is 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...
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