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Two-photon fluorescent material benzoxazolyl pyridinium salt and its preparation method and application

A technology of benzoxazolyl pyridinium salt and two-photon fluorescence, applied in the field of fluorescent materials, can solve problems such as two-photon absorption limitation, and achieve the effects of low cost, easy operation and easy availability of raw materials

Active Publication Date: 2020-11-06
ANHUI UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] However, at present, the two-photon absorption cross-section of general materials is usually many orders of magnitude smaller than the single-photon absorption cross-section, resulting in many restrictions on the practical application of two-photon absorption.

Method used

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  • Two-photon fluorescent material benzoxazolyl pyridinium salt and its preparation method and application
  • Two-photon fluorescent material benzoxazolyl pyridinium salt and its preparation method and application
  • Two-photon fluorescent material benzoxazolyl pyridinium salt and its preparation method and application

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Embodiment 1

[0041] The preparation method of two-photon fluorescent material benzoxazolyl pyridinium salt, see figure 1 , including the following steps:

[0042] A, the preparation of intermediate M1

[0043] Weigh 20.4g (0.15mol) of p-toluic acid and 35.97g (0.33mol) of o-aminophenol, put them in a 250mL three-neck flask, add 1500mL of polyphosphoric acid, under nitrogen protection, reflux at 220°C for 6h, and then the obtained reaction Cool the liquid to 80°C, pour it into a large beaker with ice water, add an appropriate amount of saturated NaOH aqueous solution dropwise to adjust the pH of the solution to 7-8, use 300mL of ethyl acetate for multiple extractions, then spin dry the ethyl acetate, and then Ethanol recrystallization was carried out to obtain 9.84 g of solid, namely intermediate M1, with a yield of 31%.

[0044] Intermediate M1 1 H NMR: (400MHz, CD 2 Cl 2): δ(ppm)8.17(s,2H),7.77(s,1H),7.63(s,1H),7.38(s,4H),2.48(s,2H). 13 C NMR: (100MHz, CD 2 Cl 2 ):δ(ppm)163.58,151...

Embodiment 2

[0061] Preparation method of two-photon fluorescent material benzoxazolylpyridinium salt

[0062] This embodiment is similar to Embodiment 1, and for the sake of concise description, only the differences will be described. Their difference is: in step A of this example, reflux was carried out at 210°C for 7 hours, and the yield of M1 was 30.5%. The yield is 58%. In step C, the yield of M3 is 75% under reflux at 40°C for 8h. In step D, the yield of M4 is 59% under reflux at 140°C for 10h. In step E, it is The temperature was raised to 50° C. and reacted at this temperature for 3 hours, the yield of M5 was 70%. In step F, the reaction was carried out at 60° C. for 7 hours, and the yield of the target product L was 61%.

Embodiment 3

[0064] Preparation method of two-photon fluorescent material benzoxazolylpyridinium salt

[0065] This embodiment is similar to Embodiment 1, and for the sake of concise description, only the differences will be described. Their differences are: in step A of this example, reflux was carried out at 240°C for 4 hours, and the yield of M1 was 30%. The yield is 56%. In step C, the yield of M3 is 76% under reflux at 60°C for 7h. In step D, the yield of M4 is 58% under reflux at 140°C for 14h. In step E, it is Raise the temperature to 40° C. and react at this temperature for 6 h, the yield of M5 is 69%. In step F, the reaction is carried out at 90° C. for 4 h, and the yield of the target product L is 59%.

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Abstract

The invention discloses a two-photon fluorescent material benzoxazolylpyridinium salt and its preparation method and application. The two-photon fluorescent material benzoxazolylpyridinium salt is a water-soluble two-photon induced fluorescent material with low toxicity , and has good membrane penetration and can enter cells, and can be applied to two-photon fluorescence confocal microscopy imaging. The structural formula of the two-photon fluorescent material benzoxazolyl pyridinium salt is as follows:

Description

technical field [0001] The invention relates to the field of fluorescent materials, in particular to a two-photon fluorescent material benzoxazolylpyridinium salt and its preparation method and application. Background technique [0002] In recent years, the application of organic two-photon materials in many fields, especially in two-photon fluorescence microscopy and imaging, has received extensive attention. Compared with single-photon confocal microscope, two-photon confocal microscope has many advantages: (1) Two-photon confocal microscope can use infrared laser with longer wavelength (near infrared region) and stronger penetration ability in biological tissues as The excitation light source can greatly reduce the absorption and scattering of excitation light by biological tissues, obtain strong sample fluorescence and solve the problem of tomographic imaging of deep substances in biological tissues. (2) Since the two-photon fluorescence emission wavelength is far away ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D413/10C09K11/06G01N21/64
CPCC07D413/10C09K11/06C09K2211/1033G01N21/6486
Inventor 许洪康周虹屏刘丹王海燕孔林田玉鹏
Owner ANHUI UNIVERSITY
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