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A kind of two-photon ultra-low background fluorescent probe and its preparation method and application

A fluorescent probe and two-photon technology, applied in the field of analytical chemistry, can solve the problems of large background fluorescence interference, complex processing process, and large cell damage, and achieve the effects of improving detection sensitivity, reducing interference, and reducing sample damage.

Active Publication Date: 2022-02-08
QUFU NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

These traditional detection techniques generally have the disadvantages of large sample consumption, complex processing process, great damage to cells, and cumbersome detection process.
At present, the fluorescent probes that can be used to detect hydrogen sulfide have too much background fluorescence interference and low selectivity. However, this probe has the advantages of two-photon ultra-low background fluorescence and is easy to operate. Therefore, it is necessary to develop this probe

Method used

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  • A kind of two-photon ultra-low background fluorescent probe and its preparation method and application
  • A kind of two-photon ultra-low background fluorescent probe and its preparation method and application
  • A kind of two-photon ultra-low background fluorescent probe and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0068] Preparation of NDN

[0069] (1) Preparation of diazonium salt

[0070] 1) Add 5ml distilled water and 0.5ml concentrated sulfuric acid in the round bottom flask;

[0071] 2) Then add 0.5g p-nitroaniline and stir under ice bath;

[0072] 3) Finally, 0.25 g of sodium nitrate was added to 1 ml of distilled water, slowly added to the solution prepared in step 2), and the synthesis of NDN was continued for 5 h under ice-bath stirring.

[0073] 1) 2-naphthol 1g (7mmol) solution, add 5ml of 1M sodium hydroxide. The solvent used needs to be deoxygenated by argon gas bubbling, and then further treated with molecular sieves to obtain an anhydrous and oxygen-free solvent.

[0074] 2) Add 1 g (6.7 mmol) of diazonium salt in an ice bath and stir.

[0075] 3) The mixture was acidified with 0.5M sulfuric acid, and the product was vacuum-dried at 40-60° C. for 2 hours to obtain the product NDN.

[0076] (2) Fluorescent probe DNHF-H 2 Preparation of S

[0077] 1) The experiment w...

Embodiment 2

[0082] Preparation of NDN

[0083] (1) Preparation of diazonium salt

[0084] 3) Add 10ml distilled water and 1.0ml concentrated sulfuric acid in the round bottom flask;

[0085] 4) Then add 1.0g p-nitroaniline and stir under ice bath;

[0086] 3) Finally, add 0.5g of sodium nitrate to 2ml of distilled water, slowly add to the solution prepared in step 2), and continue to stir for 5h under ice bath

[0087] Synthesis of NDNs.

[0088] 1) 2-naphthol 1.5g (10mmol) solution, add 3M sodium hydroxide 7.5ml. The solvent used needs to be deoxygenated by argon gas bubbling, and then further treated with molecular sieves to obtain an anhydrous and oxygen-free solvent.

[0089] 2) Add 1.5 g (10 mmol) of diazonium salt in an ice bath, and stir.

[0090] 3) The mixture was acidified with 1M sulfuric acid, and the product was vacuum-dried at 40-60° C. for 2 hours to obtain the product NDN.

[0091] (2) Fluorescent probe DNHF-H 2 Preparation of S

[0092] 1) The experiment was carri...

Embodiment 3

[0097] Preparation of NDN

[0098] (1) Preparation of diazonium salt

[0099] 1) Add 10ml of distilled water and 1.5ml of concentrated sulfuric acid in a round bottom flask;

[0100] 2) Then add 1.5g p-nitroaniline and stir under ice bath;

[0101] 3) Finally, add 1g of sodium nitrate to 3ml of distilled water, slowly add to the solution prepared in step 2), and continue to stir for 5h under ice bath

[0102] Synthesis of NDNs.

[0103] 1) 2-naphthol 2g (14mmol) solution, add 10ml of 5M sodium hydroxide. The solvent used needs to be deoxygenated by argon gas bubbling, and then further treated with molecular sieves to obtain an anhydrous and oxygen-free solvent.

[0104] 2) Add 2 g (13.3 mmol) of diazonium salt in an ice bath, and stir.

[0105] 3) The mixture was acidified with 1.5M sulfuric acid, and the product was vacuum-dried at 40-60° C. for 2 hours to obtain the product NDN.

[0106] (2) Fluorescent probe DNHF-H 2 Preparation of S

[0107] 1) The experiment was c...

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Abstract

The invention relates to the field of fine chemical industry, in particular to the design, synthesis and application of a two-photon ultra-low background fluorescent molecular probe based on enone rearrangement. The synthetic method of fluorescent probe adopts the following steps: (1) NDN preparation: 2-naphthol solution is added in sodium hydroxide solution, and the reagent of anhydrous and oxygen-free is processed; Add diazonium salt in ice bath, stir ; Acidify, dry, get NDN; (2) fluorescent probe DNHF‑H 2 Preparation of S: In an anhydrous and oxygen-free environment, weigh NDN and 2,4-dinitrofluorobenzene, add them to DMF and mix evenly; add potassium carbonate, stir; heat up to 40-60°C, react; cool to room temperature and add ice water, filtered with suction to obtain a fluorescent probe. Two-photon imaging of this probe reduces photodamage to living biological samples and fluorophores, reduces background absorption and scattering, and improves spatial resolution and sensitivity.

Description

technical field [0001] The invention belongs to the field of analytical chemistry, and relates to a two-photon ultra-low background fluorescent probe and its preparation method and application. Background technique [0002] At present, traditional techniques for detecting hydrogen sulfide include chromatographic analysis, colorimetry, and electrochemical analysis. These traditional detection techniques generally have the disadvantages of large sample consumption, complex processing process, great damage to cells, and cumbersome detection process. At present, the fluorescent probes that can be used to detect hydrogen sulfide have too much background fluorescence interference and low selectivity. However, this probe has the advantages of two-photon ultra-low background fluorescence and is easy to operate. Therefore, it is necessary to develop this probe. Contents of the invention [0003] Fluorescent probes currently available for detecting hydrogen sulfide have too much ba...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C245/08C09K11/06G01N21/64
CPCC07C245/08C09K11/06G01N21/6428C09K2211/1007C09K2211/1011C09K2211/1014G01N2021/6432
Inventor 陈光李璐许洁薛俊莲胡金莲姜翱刘玉霞
Owner QUFU NORMAL UNIV
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