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Two-photon fluorescent dye based on 4-methoxyphenyl-substituted boron-dipyrromethene and diphenylaminoindenofluorene and its synthesis method

A technology of fluorine boron dipyrrole and two-photon fluorescence, which is applied in the field of fluorescent dyes, can solve the problem that the two-photon absorption cross section is not significantly improved, and achieve good single-photon and two-photon absorption and fluorescence performance, high fluorescence quantum yield, Effect of High Synthesis Yield

Active Publication Date: 2017-03-08
CHINA NAT TOBACCO QUALITY SUPERVISION & TEST CENT
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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) [6]

Method used

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  • Two-photon fluorescent dye based on 4-methoxyphenyl-substituted boron-dipyrromethene and diphenylaminoindenofluorene and its synthesis method
  • Two-photon fluorescent dye based on 4-methoxyphenyl-substituted boron-dipyrromethene and diphenylaminoindenofluorene and its synthesis method
  • Two-photon fluorescent dye based on 4-methoxyphenyl-substituted boron-dipyrromethene and diphenylaminoindenofluorene and its synthesis method

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Example 1: Synthesis of 2,6-iodofluoroboron dipyrrole fluorophore 1a

[0026] Under argon protection, add 500 mL of dichloromethane, 18.9 mmol of 2,4-dimethylpyrrole, 7.6 mmol of 4-methoxybenzaldehyde and three drops of trifluoroacetic acid as catalysts into a 1000 mL three-neck flask, and stir magnetically at room temperature After 6 h, 7,9 mmol of 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) was dissolved in 150 mL of dichloromethane, added to the above reaction solution, and continued to stir at room temperature for 15 min. Then, 10 mL of diisopropylethylamine (DIEA) and 10 mL of boron trifluoride ether solution were added to the above reaction liquid, and after stirring at room temperature for 30 min, 200 mL of water was added to quench the reaction, dichloromethane was extracted, and the liquids were separated. , dried over anhydrous sodium sulfate, the solvent dichloromethane was distilled off in vacuo, using dichloromethane:petroleum ether=1:2 as the eluent, and se...

Embodiment 2

[0028] Embodiment 2: the synthesis of diphenylamine-indenofluorene-acetylene compound 2f (R=C 4 h 9 )

[0029] (1) Synthesis of 2a

[0030] In a 250 mL three-neck round bottom flask, add 1.5 g (5.3 mmol) of indenofluorenedione, 120 mL of diethylene glycol, and then add 7.5 g of KOH and 8 mL of 98% hydrazine monohydrate. Then install a thermometer and a reflux condenser on the round-bottomed flask, and slowly heat up the temperature of the mixed solution to 160 ° C on a heating mantle with magnetic stirring. The water and excessive hydrazine hydrate generated in the reaction were removed by distillation, and then the temperature was raised to 196° C. for heating and reflux reaction for 24 h. After the reaction, the hot reaction solution was poured into the ice-water mixture containing dilute hydrochloric acid. A solid was formed and left to stand for a while. The gray solid obtained was filtered with Buchner funnel, washed with water several times, and then added to glacial ...

Embodiment 3

[0041] Embodiment 3: the synthesis of two-photon fluorescent dye TPFD (R=C 4 h 9 )

[0042] In a 10 mL Shrek reaction tube, add compound 2f (0.17 g, 0.26 mmol), Pd 2 (dba) 3(4.58 mg, 5%), tris(2-furyl)phosphine (2.32 mg, 10%) and cuprous iodide (1.9 mg, 10%), then add 0.8 mL of anhydrous DMF and 0.2 mL of freshly treated A mixed solvent of triethylamine, compound 1a (0.1 mmol) was added under nitrogen protection, and after reacting for 0.5 h at 60°C, the TLC plate detected that the raw material fluoroboron dipyrrole had completely reacted, then stopped the reaction, and poured the reaction solution into ether , transferred to a separatory funnel, washed several times with water, allowed to stand for stratification, dried the collected upper organic phase with anhydrous magnesium sulfate, filtered through a Buchner funnel to remove anhydrous magnesium sulfate, concentrated in vacuum on a rotary evaporator, The obtained blue solid was dissolved in dichloromethane and then ad...

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Abstract

The invention discloses a two-photon fluorescent dye based on 4-methoxyphenyl-substituted boron-dipyrromethene and diphenylaminoindenofluorene and its synthesis method. The two-photon fluorescent dye has a general structural formula shown in the description. In the formula, R represents a C1-C18 alkyl group. The synthesis method comprises that 1) 2, 4-dimethylpyrrole and 4-methoxybenzaldehyde as raw materials undergo a reaction to produce 2, 6-bit iodinated boron-dipyrromethene, 2) indenofluorene dione as a raw material is reduced, the reduced product undergoes an alkylation reaction, the product undergoes a bromination reaction, the product undergoes a Pd(0) catalytic amination reaction, and the product undergoes a Pd(0) and CuI catalytic Sonogashira cross-coupling reaction to produce a diphenylamino-indenofluorene-acetylene compound, 3) the two products obtained by the steps 1 and 2 undergo a reaction to produce the two-photon fluorescent dye. The dye has strong two-photon fluorescence performances. In toluene, the two-photon fluorescent dye has the maximum two-photon absorption cross section of 757 GM and a fluorescence quantum yield of 0.49. The two-photon fluorescent dye provides a novel design idea for synthesis and application of the boron-dipyrromethene-based two-photon fluorescent dye.

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 4-methoxyphenyl substituted fluoroborate dipyrrole and dianilinoindenofluorene 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 in three-dimensional optical storage [1] , two-photon fluorescence imaging [2] , two-photon optical limiting material [3] and photodynamic therapy [4] and other fields have broad application prospects. 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 to...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/00C09B57/00
CPCC07F5/022C09B57/00C09K11/06C09K2211/1007C09K2211/1011C09K2211/1014C09K2211/1029C09K2211/1055
Inventor 韩书磊陈欢刘彤付亚宁侯宏卫
Owner CHINA NAT TOBACCO QUALITY SUPERVISION & TEST CENT
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