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Two-photon fluorescent dye based on phenyl-substituted fluoroboron dipyrrole and dianilinofluorene and its synthesis method

A technology for substituting fluorine boron dipyrrole and fluorine boron dipyrrole, which is applied in the direction of azo dyes, organic dyes, luminescent materials, etc., can solve the problem that the improvement of the two-photon absorption cross section is not obvious, and achieve the improvement of the two-photon absorption cross section and high fluorescence Quantum yield, the effect of strong two-photon fluorescence performance

Active Publication Date: 2018-03-23
ZHENGZHOU UNIV
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Problems solved by technology

For example, Wang et al. introduced alkynyl electron-donating groups at the 2 and 6 positions of fluoroboron dipyrrole, but the improvement of its two-photon absorption cross section was not obvious (29-60 GM)

Method used

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  • Two-photon fluorescent dye based on phenyl-substituted fluoroboron dipyrrole and dianilinofluorene and its synthesis method
  • Two-photon fluorescent dye based on phenyl-substituted fluoroboron dipyrrole and dianilinofluorene and its synthesis method
  • Two-photon fluorescent dye based on phenyl-substituted fluoroboron dipyrrole and dianilinofluorene and its synthesis method

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Embodiment 1

[0038] The synthesis route of the two-photon fluorescent dye based on phenyl-substituted fluoroborate dipyrrole and dianilinofluorene in this example is as follows:

[0039]

[0040] Among them, R is C 2 h 5 .

[0041] The synthesis method of the two-photon fluorescent dye based on phenyl-substituted fluoroborate dipyrrole and dianilinofluorene in this embodiment is as follows:

[0042] (1) Synthesis of 2,6-iodofluoroboron dipyrrole fluorophore 1a

[0043] A1: Under argon protection, add 500 mL of dichloromethane, 18.9 mmol of 2,4-dimethylpyrrole, 7.6 mmol of benzaldehyde and 0.1 mL of trifluoroacetic acid as catalysts into a 1000 mL three-neck flask, and stir magnetically for 6 h at room temperature ;

[0044] B1: Dissolve 7.6 mmol 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) in 150 mL of dichloromethane, add it to the reaction solution obtained in step A1, and continue stirring at room temperature for 15 min;

[0045] C1: Then add 10 mL diisopropylethylamine (DIEA) and...

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Abstract

The invention discloses a phenyl-substituted bodipy and diphenylamine fluorene based two-photon fluorescent dye. A structural general formula of the fluorescent dye is represented by a formula shown in the description, wherein R is C1-C18 alkyl. Steps for synthesizing the fluorescent dye are as follows: producing 5-phenyl-substituted and 2,6-iodinated bodipy from 2,4-dimethyl pyrrole and benzaldehyde, which serve as raw materials; subjecting fluorene, which serves as a raw material, to bromination, alkylation, Pd(0) catalyzed amination, a Pd(0) and CuI catalyzed Sonogashira cross-coupling reaction and trimethylsilyl removal, so as to produce a diphenylamine-fluorene-acetylene compound; and subjecting the 2,6-iodinated bodipy and the diphenylamine-fluorene-acetylene compound to a reaction, thereby obtaining the target product. The target compound has relatively high two-photon fluorescence performance, the maximum two-photon absorption cross section in toluene reaches 265GM, and the fluorescent quantum yield is 0.35, so that a new design way of think is provided for the synthesis and application of bodipy-based two-photon fluorescent dyes.

Description

technical field [0001] The invention belongs to the technical field of fluorescent dyes, and in particular relates to a two-photon fluorescent dye based on phenyl-substituted fluoroboron dipyrrole and dianilinofluorene and a synthesis method thereof. Background technique [0002] Two-photon absorption is a third-order nonlinear optical effect. Organic materials with large two-photon absorption cross-sections have broad application prospects in the fields of three-dimensional optical storage, two-photon fluorescence imaging, two-photon optical limiting materials, and photodynamic therapy. In the research field of two-photon fluorescent dyes, the development of fluorescent dyes with larger two-photon absorption cross section is the key. [0003] Fluoroboron dipyrrole is a class of fluorescent chromophores with excellent performance. It has a large molar extinction coefficient, high fluorescence quantum yield, good photostability, good tolerance to polarity and pH, and is easy...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02C09K11/06C09B57/00
CPCC07F5/022C09B57/00C09K11/06C09K2211/1007C09K2211/1011C09K2211/1029C09K2211/1055
Inventor 郝新奇菅宁歌高翔申晓静祝智慧朱新举赵雪梅宋毛平
Owner ZHENGZHOU UNIV
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