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Near infrared organic fluorescent dye with mechanical responsiveness

A fluorescent dye and responsive technology, applied in the field of organic fluorescent dyes, can solve the problems of complex dye steps, low fluorescence quantum yield, etc., and achieve the effect of good application value

Active Publication Date: 2015-09-23
TAIYUAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Since the energy level difference between the lowest excited state and the ground state of red fluorescent dyes is small, the non-radiative inactivation of excited state dye molecules is often more effective, resulting in the fluorescence quantum yield of most red fluorescent dyes is not high, and such dyes Synthesis requires more complex steps
Therefore, there are relatively few near-infrared or red-emitting organic dyes that are mechanoresponsive.

Method used

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  • Near infrared organic fluorescent dye with mechanical responsiveness
  • Near infrared organic fluorescent dye with mechanical responsiveness
  • Near infrared organic fluorescent dye with mechanical responsiveness

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Add 139.4mg (0.4mmol) of 3-butyl-2,5-bis(4-formylphenyl)thiophene and 128.6mg (0.88mmol) of 1,3-indanedione into a 50mL round bottom flask, add anhydrous Dissolve 15 mL of ethanol, add a few drops of acetic acid and triethylamine at the same time, and stir the reaction at room temperature. After the reaction is complete, stand and filter to obtain purple-red powder, recrystallize with absolute ethanol to obtain bright red needles. The bright red needles were completely dissolved in dichloromethane, and the solvent dichloromethane was quickly removed on a vacuum rotary evaporator to obtain 215.7 mg of crystalline organic fluorescent dye dark red powder, with a yield of 89.2%.

[0031] 1 H-NMR (400 MHz, CDCl 3 , ppm): δ= 8.57~8.53 (q, 4H); 8.04~8.00 (m, 4H); 7.92 (s, 1H); 7.90 (s, 1H); 7.84~7.81 (m, 4H); 7.76 (d , 2H); 7.65 (d, 2H); 7.41 (s, 1H); 2.75 (t, 2H); 1.68 (m, 2H); 1.36 (m, 2H);

[0032] MALDI-TOF-MS: [M] + cacld.C 40 h 28 o 4 S, 604.1708; found: 604.170...

Embodiment 2

[0034] Add 150.6mg (0.4mmol) of 3-hexyl-2,5-bis(4-formylphenyl)thiophene and 128.6mg (0.88mmol) of 1,3-indanedione into a 50mL round bottom flask, add absolute ethanol 15mL was dissolved, and a few drops of acetic acid and triethylamine were added at the same time, and the reaction was stirred at room temperature. After the reaction is complete, stand and filter to obtain purple-red powder, recrystallize with absolute ethanol to obtain bright red needles. The bright red needles were completely dissolved in dichloromethane, and the solvent dichloromethane was quickly removed on a vacuum rotary evaporator to obtain 220 mg of crystalline organic fluorescent dye dark red powder with a yield of 86.9%.

[0035] 1 H-NMR (400 MHz, CDCl 3 , ppm): δ= 8.58~8.54 (q, 4H); 8.05~8.01 (m, 4H); 7.93 (s, 1H); 7.89 (s, 1H); 7.85~7.82 (m, 4H); , 2H); 7.66 (d, 2H); 7.43 (s, 1H); 2.78 (t, 2H); 1.72 (m, 2H); 1.39 (m, 2H); 1.31 (m, 4H); 3H).

[0036] MALDI-TOF-MS: [M] + cacld.C 42 h 32 o 4 ...

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Abstract

The invention discloses a near infrared organic fluorescent dye with mechanical responsiveness. The near infrared organic fluorescent dye with the mechanical responsiveness is dark red crystalline powder with a compound with the following structure formula, the crystalline powder is obtained through the mode that the compound is dissolved in an organic solvent capable of dissolving the compound, and then the organic solvent is removed through vacuum rotary evaporation. The near infrared organic fluorescent dye is changed from a crystalline state to an amorphous state under the mechanical force effect, under the excitation of blue rays, 620 nm macroscopic red fluorescence can be emitted, the absolute fluorescence quantum yield is above 11%, after the steam fumigation of the organic solvent, the near infrared organic fluorescent dye can be changed from the amorphous state to the crystalline state, the fluorescence is deactivated, and the fluorescence quantum yield is 0. The features of the near infrared organic fluorescent dye with the mechanical responsiveness have good application prospect at aspects of anti-counterfeiting, stress probe / detection, sensors and fluorescent probes. (please see the formula in the instruction).

Description

technical field [0001] The invention relates to an organic fluorescent dye. The organic fluorescent dye can emit red fluorescence after mechanical force action. Background technique [0002] Organic fluorescent dyes have been widely used in organic electroluminescent diodes, organic solid-state lasers, and bioluminescent imaging, making them a research hotspot in science and industry. Especially red fluorescent dye, because it is an important part of the three-primary color red, green and blue full color scheme, and the penetration of red light to biological tissues is far better than other colors, it can be used for bioluminescence labeling and imaging, etc. The development of organic red fluorescent dyes has important research significance and application prospects. [0003] Most organic fluorescent dyes have strong fluorescence emission in dilute solution, but show no fluorescence or weak fluorescence in solid state, which greatly limits the practical application of orga...

Claims

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Application Information

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IPC IPC(8): C09K11/06C09B23/10C07D333/22
Inventor 郭鹍鹏李洁王华成君武钰铃梁效中曹亚雄
Owner TAIYUAN UNIV OF TECH