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Adamantyl-modified near-infrared squaraine dye as well as preparation method and application thereof

An adamantyl and infrared square technology is applied in the field of adamantyl-modified near-infrared squaraine dyes and their preparation, which can solve the problems of limited application, easy aggregation, fading and the like, and achieves improved solubility, excellent optical properties, and stability. good effect

Inactive Publication Date: 2014-07-16
FUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But like most near-infrared dyes, they have a low HOMO-LUMO energy band, so the 1,3-position of the central four-membered ring is easily attacked by nucleophiles and faded; in addition, the planar structure of squarylium dyes makes them Easily aggregated in polar solvents, causing absorption band broadening and fluorescence quenching
These two features limit some of its applications in the biological field

Method used

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  • Adamantyl-modified near-infrared squaraine dye as well as preparation method and application thereof
  • Adamantyl-modified near-infrared squaraine dye as well as preparation method and application thereof
  • Adamantyl-modified near-infrared squaraine dye as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] 1-Adamantyl-modified amide derivatives , n = 0 preparation:

[0052] In a 50 mL round bottom flask, add 1-adamantanecarboxylic acid (1.00 g, 5.55 mmol), 5 mL of thionyl chloride, at 85 ° C was refluxed for 1 h. Cool to room temperature after the reaction, and distill off excess thionyl chloride under reduced pressure. Add 5 mL of dry toluene to the above-mentioned reaction flask, add 10 mL of a toluene solution of N-methylaniline (1.00 mL, 9.23 mmol) dropwise at room temperature, and complete the dropwise addition in about 2 h, and continue stirring for 1 h after the dropwise addition. After the reaction stopped, washed several times with water, dried and removed the solvent under reduced pressure, then separated by silica gel column chromatography, the developing solvent was petroleum ether:ethyl acetate (v / v)=50:1, and 1.20 g of white solid was obtained with a yield of 80 %. Melting point: 104-105℃; IR (KBr): 3059 (Ar-H), 2901, 2850 (C-H), 1628 (C=O) cm -1 ; 1 ...

Embodiment 2

[0054] 1-Adamantyl-modified amide derivatives , n = 1 preparation:

[0055] In a 50 mL reaction flask, add 1-adamantaneacetic acid (1.00 g, 5.15 mmol), 5 mL thionyl chloride, and reflux for 3 h. After the reaction stopped, it was cooled, and excess thionyl chloride was removed under reduced pressure, and the obtained product was directly used in the next reaction. Add 10 mL of dry toluene to the above-mentioned reaction flask, add 10 mL of a toluene solution of N-methylaniline (1.50 mL, 13.8 mmol) dropwise at room temperature, and complete the dropwise addition in about 2 h, and continue stirring for 3 h after the dropwise completion. After removing the solvent under reduced pressure, separate by silica gel column chromatography, gradient elution, first rinse with petroleum ether: ethyl acetate (v / v) = 100:1, remove excess N-methylaniline, and then use petroleum ether: Ethyl acetate (v / v)=30:1 was used as developing solvent to elute, and 1.43 g of white solid was obtained w...

Embodiment 3

[0057] 1-adamantyl modified aniline derivatives , n = 0 preparation:

[0058] In a 50 mL three-neck flask, add 1-adamantyl-modified amide derivatives, n = 0 (0.54 g, 2.00 mmol), NaBH 4 (0.18 g, 4.76 mmol) and 10 mL of dry THF, cooled to 0 ° c. then in N 2 Under protection, drop 20 mL dissolved in I 2 (1.00 g, 3.94 mmol) in THF, drop it within 2.5 h. Rise to 70 after dripping ° C, continue to react for 36 h. After the reaction was completed, it was cooled to room temperature, and a small amount of water was added to quench the reaction. After removing most of the solvent under reduced pressure, add 30 mL of ether, wash with water, anhydrous MgSO 4dry. After the solvent was removed under reduced pressure, it was separated by silica gel column chromatography with petroleum ether as the eluent to obtain 80 mg of a colorless viscous liquid with a yield of 16%. IR (KBr): 2895, 2883, 2844, 2817, 1610, 1597, 1506, 1448, 1360, 1236, 1182, 743, 689 cm -1 ; 1 H NMR (400 MHz,...

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Abstract

The invention discloses an adamantyl-modified near-infrared squaraine dye as well as a preparation method and application thereof. The preparation method comprises the following steps: (1) mixing an adamantine-modified aniline derivative with squaric acid, dissolving the mixture in proper solvents, connecting the solution with a water knockout drum, and carrying out reflux for several hours under the protection of N2; (2) cooling the reaction mixture obtained in the step (1) to the room temperature, and removing the solvents at reduced pressure, thus obtaining a crude product; (3) washing the crude product with petroleum ether for several times, and then purifying the product through silica gel column chromatography, thus obtaining the adamantyl-modified near-infrared squaraine dye product. The adamantyl-modified near-infrared squaraine dye and the preparation method have the prominent advantages that the squaraine dye has good stability and excellent optical property; the solubility of the dye in the water solution can be effectively improved after the squaraine dye is included by cyclodextrin; the squaraine dye can serve as a fluorescently and colorimetrically responsive pH probe; the 2-adamantyl-modified near-infrared squaraine dye is successfully applied to intracellular imaging of living cells so as to detect intracellular pH values.

Description

technical field [0001] The invention belongs to the field of organic chemistry, and in particular relates to an adamantyl-modified near-infrared squarylium dye, a preparation method and application thereof. Background technique [0002] The emission wavelength of near-infrared fluorescent dyes is between 650-900 nm. In this range, the autofluorescence of biomolecules is weak, which can avoid the interference of biological background and obtain high analytical sensitivity (Shi Feng; Li Hongyang; Peng Xiaojun. Bioanalysis Near Research progress of infrared fluorescent dyes. Fine Chemicals 2003, 20 , 268-272.), and red light with a wavelength >650 nm can penetrate animal skin and tissues, so the application of near-infrared dyes as fluorescent probes in biological analysis and cell imaging has attracted widespread attention. Squaric acid dyes are 1,3-disubstituted derivatives produced by condensation of squaryl acid with electron-rich aryl compounds or aniline derivatives....

Claims

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Application Information

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IPC IPC(8): C09B57/00C09K11/06G01N21/64G01N21/33
Inventor 傅南雁王桂美
Owner FUZHOU UNIV
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