Perylene diimide fluorescent dye with ortho-substituted benzanthrone, and preparation ,method and application thereof

A technology of perylene diimide and benzoanthrone, which is applied in the field of organic nonlinear optical materials, can solve problems such as fluorescence quenching, achieve large application potential, large two-photon absorption cross-section value, and improve third-order nonlinear optics. active effect

Active Publication Date: 2021-08-31
SHANTOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, since perylene diimide itself is a compound with a large π-conjugated system, it is prone to π-π stacking in vivo, which eventually leads to fluorescence quenching.
At present, the ortho-position modification of perylene diimide is relatively small, so the fluoropho

Method used

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  • Perylene diimide fluorescent dye with ortho-substituted benzanthrone, and preparation ,method and application thereof
  • Perylene diimide fluorescent dye with ortho-substituted benzanthrone, and preparation ,method and application thereof
  • Perylene diimide fluorescent dye with ortho-substituted benzanthrone, and preparation ,method and application thereof

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Embodiment 1

[0038] A kind of preparation of the perylene diimide derivative (compound 5) of ortho-substituted benzanthrone, its reaction formula is as follows:

[0039]

[0040] It mainly includes the following steps: add the 2-brominated 7-tridecyl substituted perylene diimide derivative (compound 4, 0.69g, 0.83mmol) into the two-necked bottle, and introduce boric acid at the 3rd position Benzoanthrone derivative of pinacol ester (compound 2, 0.59g, 1.66mmol), tetrakis(triphenyl)phosphine palladium (0.05g, 0.04mmol) catalyst and potassium carbonate (0.23g, 1.66mmol), extraction Nitrogen was circulated in vacuum three times, and 30ml of N,N-dimethylformamide was injected into the reaction flask with a syringe. Heat to 80°C, 1000r / min, and react for 12 hours. Cool to room temperature after the reaction, remove excess solvent with a rotary evaporator, add 50 mL of dichloromethane solution to dissolve the solid, wash with 20 mL of distilled water, and separate the layers. Use anhydrous ...

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Abstract

The invention relates to a perylene diimide fluorescent dye with ortho-substituted benzanthrone. 3, 4, 9, 10-perylenetetracarboxylic diimide is used as a core group, imide nitrogen atoms at two ends of the core group are connected with 7-tridecyl, and the ortho-position of the core group is connected with benzanthrone. The 7-tridecyl group is introduced to the perylene diimide group, and the benzanthrone group is introduced to the ortho position, so that the obtained perylene diimide fluorescent dye of ortho-substituted benzanthrone has a large two-photon absorption cross section value, the third-order nonlinear optical activity is greatly improved, and the perylene diimide fluorescent dye can be applied to a third-order nonlinear optical material. Meanwhile, no matter whether single photons or two photons are used for exciting the aggregation states of the two photons, the perylene diimide fluorescent dye with ortho-substituted benzanthrone shows AIE properties, and has great application potential in the aspects of two-photon fluorescence imaging and two-photon dynamic therapy.

Description

technical field [0001] The invention relates to the field of organic nonlinear optical materials, in particular to a perylene diimide fluorescent dye with ortho-substituted benzanthrone and its preparation and application. Background technique [0002] Organic nonlinear optical materials have the advantages of multiple relationship between absorption wavelength and emission wavelength, fast response time, and easy processing into high-quality optical devices. They have great potential significance in information technology and industrial applications. The two-photon absorption (TPA) effect is a phenomenon in which molecules are excited by light under laser light, and it is a kind of third-order nonlinear optical effect. The molecule simultaneously absorbs two photons of the same or different frequencies, producing a very high transient photon density. Two-photon absorption has attracted great interest due to its many advantages, especially when applying this technique to ph...

Claims

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Application Information

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IPC IPC(8): C07D471/06C09K11/06A61K49/00A61K41/00C09B57/00G01N21/64
CPCC07D471/06C09K11/06A61K49/0021A61K41/008C09B57/00G01N21/6428G01N21/6456C09K2211/1011C09K2211/1044G01N2021/6432G01N2021/6439
Inventor 许良龙雪婷鲁福身郑育森张文英
Owner SHANTOU UNIV
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