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Pyrene HPTS (8-Hydroxypyrene-1,3,6-trisulfonic acid) series derivative and synthesis method

A synthesis method and derivative technology, applied in the field of HPTS series derivatives and synthesis, can solve the problems of strong water solubility of HPTS, easy leakage of fluorescent dyes, narrow application range, etc., and achieve increased hydrophobicity, broadened application range, and low toxicity Effect

Active Publication Date: 2018-10-02
NANJING UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] Aiming at the problems of strong water solubility of HPTS, limited application in the natural environment, easy leakage of fluorescent dyes, and narrow application range, the invention provides a series of HPTS derivatives and a synthesis method

Method used

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  • Pyrene HPTS (8-Hydroxypyrene-1,3,6-trisulfonic acid) series derivative and synthesis method
  • Pyrene HPTS (8-Hydroxypyrene-1,3,6-trisulfonic acid) series derivative and synthesis method
  • Pyrene HPTS (8-Hydroxypyrene-1,3,6-trisulfonic acid) series derivative and synthesis method

Examples

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Embodiment 1

[0044] In this example, 8-hydroxypyrene-1,3,6-trisodium trisulfonate (HPTS) is used as a precursor to synthesize 8-hydroxy-1,3,6-trisulfdiethylamine (HPTS-diethylamine), and the synthesis steps are as follows :

[0045] 1) Put HPTS and phosphorus oxychloride into reaction according to 1:3 equivalent, DMF catalyzes, heats and refluxes for 12 hours;

[0046] 2) Slowly introduce the reaction product in step 1) into ice water and stir to precipitate a solid, and obtain HPTS-SO by suction filtration 2 Cl. Yield 90%.

[0047] 3) the HPTS-SO obtained in step 2) 2 Cl was dissolved in an appropriate amount of tetrahydrofuran (THF) to prepare a concentration of 0.3mmol mL -1 solution A, dimethylamine was dissolved in an appropriate amount of tetrahydrofuran (THF) according to 3 times the equivalent, and prepared to a concentration of 0.5mmol mL -1 solution B.

[0048] 4) Slowly add solution B dropwise to solution A and react at room temperature for 24 hours, then spin evaporate to...

Embodiment 2

[0053] In this embodiment, 8-hydroxypyrene-1,3,6-trisodium trisulfonate (HPTS) is used as a precursor to synthesize HPTS-n-butylamine; the steps of its synthesis method are as follows:

[0054] 1) Put HPTS and phosphorus oxychloride into reaction according to the equivalent ratio of 1:3.1, catalyze with DMF, and heat to reflux for 12 hours.

[0055] 2) Slowly introduce the reaction product in step 1) into ice water and stir to precipitate a solid, and obtain HPTS-SO by suction filtration 2 Cl. Yield 90%.

[0056] 3) the HPTS-SO obtained in step 2) 2 Cl was dissolved in an appropriate amount of tetrahydrofuran (THF) to prepare a concentration of 0.3mmol mL -1 The solution A of the solution A was prepared by dissolving 3.1 equivalents of n-butylamine in an appropriate amount of tetrahydrofuran (THF) to a concentration of 0.5 mmol mL -1 solution B.

[0057] 4) Slowly add solution B to solution A drop by drop, react at room temperature for 24 hours, and spin evaporate to obta...

Embodiment 3

[0062] In this embodiment, 8-hydroxypyrene-1,3,6-trisodium trisulfonate (HPTS) is used as a precursor to synthesize HPTS-ethyl ester; the steps of its synthesis method are as follows:

[0063] 1) Put HPTS and phosphorus oxychloride into the reaction according to the equivalent ratio of 1:4, DMF catalyzes, heat and reflux for 12 hours.

[0064] 2) Slowly introduce the reaction product in step 1) into ice water and stir to precipitate a solid, and obtain HPTS-SO by suction filtration 2 Cl. Yield 90%.

[0065] 3) the HPTS-SO obtained in step 2) 2 Cl was dissolved in tetrahydrofuran (THF) to prepare a concentration of 0.3mmol mL -1 solution A, according to 4 times the equivalent of absolute ethanol dissolved in tetrahydrofuran (THF), prepared to a concentration of 0.5mmol mL -1 solution B.

[0066] 4) Slowly add solution B to solution A drop by drop, react at room temperature for 24 hours, and rotate to obtain the product. After column separation, the pure product of 8-hydrox...

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Abstract

The invention discloses a pyrene HPTS (8-Hydroxypyrene-1,3,6-trisulfonic acid) series derivative and a synthesis method, and belongs to the technical field of organic synthesis. The HPTS series derivative is prepared from HPTS by introducing alkylamine or alcohol into sulfonic acid groups. The synthesis method comprises the following steps: 1) putting HPTS and phosphorus oxychloride into reaction,and performing heating and refluxing for 12 h under catalysis of DMF to obtain a reaction product; 2) introducing the reaction product into ice water, performing stirring, separating out solid, and performing suction filtration to obtain HPTS-SO2Cl; 3) dissolving HPTS-SO2Cl in tetrahydrofuran to prepare a solution A, dissolving alkyl amine or alcohol in tetrahydrofuran to prepare a solution B, mixing the solution A with the solution B for reaction for 24 h at room temperature, performing rotary evaporation to obtain a product, and obtaining a pure compound after column separation. The derivative has higher lipid solubility, overcomes the defects of high water solubility and limited application range of HPTS and widens the application range of HPTS.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and relates to a series of HPTS derivatives and a synthesis method. Background technique [0002] HPTS is 8-hydroxy-1,3,6-trisulfonic acid pyrene, which is a kind of fluorescent material with spectral selectivity to pH change, and has the characteristics of green-blue fluorescence emission, so it is widely selected as a fluorescent material. Dyes Fluorescent dyes applied to pH changes. Not only that, but HPTS is also a water-soluble fluorescent substance with extremely low toxicity. It exists in the form of protonated state and deprotonated state in aqueous solution according to the pH environment. HPTS has a high photon quantum yield and a large These properties make HPTS very suitable for the development of fluorescent materials in the field of human health and environmental monitoring, but at the same time, because of its strong water solubility, its application in natural environments is lim...

Claims

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Application Information

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IPC IPC(8): C09B57/00C09K11/06C07C303/38C07C311/29C07C303/28C07C309/75
CPCC09K11/06C07C303/02C07C303/28C07C303/38C07C309/75C07C311/29C09B57/00C07C2603/50C09K2211/1011C07C309/87C09B57/001
Inventor 罗军胡璇梁潮根方文刘兆东尹带霞
Owner NANJING UNIV
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