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Two-photon fluorescent probe of benzoindole derivative and preparation method and application thereof

A benzoindole derivative, two-photon fluorescence technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of inability to detect low concentration, complex sample pretreatment, low detection sensitivity, etc. Small sampling volume, high sensitivity, high sensitivity effect

Inactive Publication Date: 2017-05-17
ANHUI UNIVERSITY
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Problems solved by technology

However, these detection methods have disadvantages such as complicated sample pretreatment, time-consuming, complicated operation procedures, etc.
In addition, the detection sensitivity of these methods is low, that is, they cannot detect low concentrations of HSO 3 -

Method used

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  • Two-photon fluorescent probe of benzoindole derivative and preparation method and application thereof
  • Two-photon fluorescent probe of benzoindole derivative and preparation method and application thereof
  • Two-photon fluorescent probe of benzoindole derivative and preparation method and application thereof

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Embodiment Construction

[0040] The preparation method of the benzindole derivative two-photon fluorescent probe in this embodiment is as follows:

[0041] 1. Synthesis of intermediate OT

[0042] Add 3.51g (10mmol) of 2,3,3-trimethylbenzindole to a 50mL round-bottomed flask, add 2.8g (20mmol) of methyl iodide at room temperature, mix well and stir at room temperature for 24h. After the reaction A white precipitate is formed (if the precipitate contains a small amount of impurities, it can be washed with an appropriate amount of ethanol), and 3.3 g of a white solid is obtained by suction filtration, which is the intermediate OT, and the yield is 94%.

[0043] 2. Synthesis of target product L

[0044] Add 3.51g (10mmol) of intermediate OT, 1.1g (10mmol) of 4-pyridinecarbaldehyde and 30mL of ethanol to a 100mL three-necked flask in turn, add 2 drops of catalyst hexahydropyridine under stirring, and then raise the temperature to 60°C for 6 hours. The solution turned purple, and a red solid was precipit...

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Abstract

The invention discloses a two-photon fluorescent probe of a benzoindole derivative and a preparation method and an application thereof. A structural formula of the two-photon fluorescent probe of the benzoindole derivative is shown in description. The two-photon fluorescent probe has the advantages that a benzoindole group with higher reaction activity and good biocompatibility is used as a main body, and reacts with 4-pyridylaldehyde, so that an indole derivative L with a phi-conjugated system is concisely and efficiently prepared, and is subject to anion identification and activity screening; the results show that the indole derivative L has the property of singly identifying HSO3-, and the single-photon fluorescence and two-photon fluorescence are obviously changed before and after identification; cell experiments show that when the indole derivative L is used as the two-photon fluorescent probe, the indole derivative L can penetrate through a cell membrane, so as to detect the cytoplasm exogenous H3O3-.

Description

technical field [0001] The invention relates to a two-photon fluorescent probe, in particular to a benzindole derivative two-photon fluorescent probe and its preparation method and application. Background technique [0002] With the development of two-photon technology, the advantages of two-photon fluorescent materials in biological applications have attracted more attention. First of all, during the use of biologically specific two-photon fluorescent materials, the excitation light source is located in the near-infrared / infrared region, which has stronger penetrating ability; secondly, within the excitation range of two-photon fluorescent materials, it effectively avoids Biological autofluorescence interferes with the luminescent properties of the material itself; third, only the molecules near the focal point are excited when the two-photon fluorescent material is excited, which can significantly reduce the damage of the laser to the molecules and reduce photobleaching. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/06C09K11/06G01N21/64
CPCC07D401/06C09K11/06C09K2211/1029G01N21/6486
Inventor 张琼祝英忠宋磊磊徐颖吴杰颖田玉鹏李胜利周虹屏李飞
Owner ANHUI UNIVERSITY
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