Temperature-sensitive dendritic perylene and its preparation method

A temperature-sensitive, dendritic technology, applied in chemical instruments and methods, organic chemistry, organic dyes, etc., can solve problems such as application limitations, and achieve flexible detection and flexible selection

Inactive Publication Date: 2016-06-29
SHANGHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although there are more and more studies on the modification of dye perylene, the reports of perylene with temperature-sensitive behavior are very rare. Although the PNiPAM-modified perylene reported by Bai et al. has temperature-sensitive characteristics, because PNIPAM has certain toxicity, this kind of Dyes have limitations in application to biological materials
In addition, monodisperse perylenes with temperature-sensitive behavior after modification have not been reported

Method used

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  • Temperature-sensitive dendritic perylene and its preparation method
  • Temperature-sensitive dendritic perylene and its preparation method
  • Temperature-sensitive dendritic perylene and its preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Take the synthesis of perylene modified with a first-generation alkoxyether dendron as an example. Specific synthetic route reference figure 1 .

[0031] 1. Synthesis of a first-generation alkoxyether dendron with an amino group as the core point

[0032] In this example, the synthesis of G1-OH refers to references (WenLi, Afang Zhang, and A. Dieter Schlü1ter, Macromolecules 2008, 41, 43-49.), Ts-TEG-N 3 The synthesis refers to references (DennisM.Bauer, IshtiaqAhmed, Antonina Vigovskaya, and LjiljanaFruk, Bioconjugate Chem.2013, 24, 1094-1101.; RajibK.Goswami, YuanLiu, ChengLiu, RichardA.Lerner, and SubhashC.Sinha, Mol.Pharmaceutics0, 2013, 1 -543.) Compound G1-OH (1.51g), Compound KI (0.12g), Compound NaH (0.40g) and Compound 15-crown-5 (0.57g) were dissolved in dry THF (30mL) and cooled to 0 o C~5 o Below C, compound Ts-TEG-N 3 (0.99g) was dissolved in dry THF (20mL), added dropwise into the reaction bottle and stirred for 30min, then the system was gradually r...

Embodiment 2

[0038] Take the synthesis of perylene modified with the second-generation alkoxyether dendron as an example. Specific synthetic route reference figure 1 .

[0039] 1. Synthesis of the second-generation alkoxyether dendron with the core point as the amino group

[0040] In this example, the synthesis of G1-OH refers to references (WenLi, Afang Zhang, and A. Dieter Schlü1ter, Macromolecules 2008, 41, 43-49.), Ts-TEG-N 3 The synthesis refers to references (DennisM.Bauer, IshtiaqAhmed, AntoninaVigovskaya, and LjiljanaFruk, BioconjugateChem.2013, 24, 1094-1101.; RajibK.Goswami, YuanLiu, ChengLiu, RichardA.Lerner, and SubhashC.Sinha, Mol.Pharmaceutics0, 2013, 1 -543.) Compound G2-OH (500.00 mg), compound KI (29.65 mg), compound NaH (31.2 mg) and compound 15-crown-5 (49.94 mg) were dissolved in dry THF (20 mL), cooled to 0 o C~5 o Below C, compound Ts-TEG-N 3 (82.34mg) was dissolved in dry THF (10mL), added dropwise into the reaction flask and stirred for 30min, then the system...

Embodiment 3

[0046] Temperature-sensitive behavior test of aqueous solution of temperature-sensitive dendritic perylene.

[0047] 1. Temperature-sensitive behavior of a first-generation dendritic perylene (G1TEGPBI) aqueous solution

[0048] In this example, G1TEGPBI was dissolved in water to prepare a concentration of C=1×10 -4 M's solution. The aqueous solution is clear and red at room temperature. When the temperature is heated to a certain level, larger solid particles are precipitated and the color becomes lighter. When the temperature drops to room temperature, the solution returns to the previous state. This process can Completely iterative.

[0049] 2. Temperature-sensitive behavior of the second-generation dendritic perylene (G2TEGPBI) aqueous solution

[0050] In this example, G2TEGPBI was dissolved in water to prepare a concentration of C=1×10 -4 M's solution. The solution is also clear and red at room temperature. When the temperature is heated to a certain temperature, un...

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Abstract

The invention relates to a temperature-sensitive dendronized perylene and a preparation method thereof. The dendronized perylene is a dendronized compound which is formed by introducing alkoxy ether dendronized elements each with an amino group at the nuclear point to the two ends of a dye perylene by virtue of a chemical reaction. Besides, the aqueous solution of the perylene has excellent opto-chemical properties and the opto-chemical characteristics of the aqueous solution of the perylene can be changed by regulating temperature, namely, the positions and the intensity of the fluorescent absorption peaks of the aqueous solution of the perylene are changed correspondingly as the temperatures are increased, and on this basis, the perylene can be applied to a temperature sensor. Compared with other modified perylene, the temperature-sensitive dendronized perylene has the characteristics of simple preparation, flexible selection, wide temperature detection range and the like, and thus has important application value in many fields such as photoelectric and biological sensors.

Description

technical field [0001] The invention relates to a dendritic perylene and a preparation method thereof, in particular to a temperature-sensitive dendritic perylene and a preparation method thereof. Background technique [0002] In recent years, perylene has attracted much attention as a well-known fluorescent dye. It can exhibit high light and thermal stability and excellent photoelectric properties, which make it have broad application prospects in the fields of organic transistors, phototubes, laser dyes, biological probes, etc. [0003] The structure of perylene contains many benzene rings, and the π-π interaction is strong, resulting in poor water solubility and easy aggregation. These characteristics limit the application of perylene in water-soluble biological systems. Chemical modification of dye perylene to improve its water solubility and endow it with functionality according to its structural characteristics has become a current research hotspot, such as introducin...

Claims

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Application Information

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Patent Type & AuthorityPatents(China)
IPC IPC(8): C07D471/06C09K11/06
CPCC07D471/06C09B5/00C09K11/06C09K2211/1029
Inventor李文张晓茜张夏聪闫家涛李娟张修强赵鑫刘连晓张阿方
OwnerSHANGHAI UNIV