Phenyl-substituted bodipy and diphenylamine fluorene based two-photon fluorescent dye and synthesis method therefor

A fluoroboron-substituted dipyrrole and two-photon fluorescence technology, applied in the field of fluorescent dyes, can solve the problem of insignificant improvement of the two-photon absorption cross-section, and achieve the improvement of the two-photon absorption cross-section, strong two-photon fluorescence performance, and high fluorescence quantum yield. Effect

Active Publication Date: 2017-03-08
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 fluorob

Method used

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  • Phenyl-substituted bodipy and diphenylamine fluorene based two-photon fluorescent dye and synthesis method therefor
  • Phenyl-substituted bodipy and diphenylamine fluorene based two-photon fluorescent dye and synthesis method therefor
  • Phenyl-substituted bodipy and diphenylamine fluorene based two-photon fluorescent dye and synthesis method therefor

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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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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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