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Synthesis of cyanine, coumarin and dicarbonyl boron fluoride hybrid fluorochrome and application thereof

A technology of boron dicarbonyl fluoride and coumarin, which is applied in the field of synthesis of new hybrid fluorescent dyes, can solve problems such as limited application range, small Stokes shift, and short absorption and emission wavelengths, and achieves short synthesis routes and optical Improved properties and simple reaction conditions

Active Publication Date: 2019-08-30
QINGDAO UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Common dye core structures are usually divided into coumarin dyes, cyanine dyes, BODIPY dyes, rhodamine dyes and benzothiadiazole dyes, etc., but each has its own disadvantages such as short absorption and emission wavelengths, Poor photostability, small Stokes shift, etc.
[0005] The photophysical and photochemical properties of coumarin are stable, but its application range is limited due to its short absorption and emission wavelength (400-520nm), and research has found that the 7-position of its mother nucleus is introduced into an electron-donating system, and the 3 or 4-position is introduced into an electron-withdrawing system It can make its absorption and emission wavelength red shift
Difluoroboron is a strong electron-deficient system, a very good electron acceptor and stable in nature, but its Stokes shift is generally small such as BODIPY dyes (15-30nm), which makes it more affected by its own excitation light
The absorption and emission wavelengths of cyanine dyes are generally longer, and the molar extinction coefficient is large, but their photostability is poor, and the long methine chains are easy to break under light.

Method used

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  • Synthesis of cyanine, coumarin and dicarbonyl boron fluoride hybrid fluorochrome and application thereof
  • Synthesis of cyanine, coumarin and dicarbonyl boron fluoride hybrid fluorochrome and application thereof
  • Synthesis of cyanine, coumarin and dicarbonyl boron fluoride hybrid fluorochrome and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Preparation of intermediate 1: Weigh 5.80g (0.03mol) of 4-diethylamino salicylaldehyde in a 250mL flask and 3.78g (0.03mol) of 4-hydroxy-6-methylpyrone dissolved in 50mL of water, then add 0.345 g (0.003mol) L-proline, stirred and refluxed at 80°C for 2 hours, a large amount of brown solid precipitated out, and the reaction was detected by TLC until the reaction was complete. After cooling, the brown solid was filtered out with suction, recrystallized with 40 mL of ethanol, and vacuum-dried after suction filtration to obtain 7.86 g of yellow-brown crystals with a yield of 86.9%. 1 H NMR (500MHz, CDCl 3 )δ16.26(s,1H),8.52(s,1H),7.40(d,J=8.8Hz,1H),6.99(d,J=1.9Hz,1H),6.63(dd,J=9.0,2.4 Hz, 1H), 6.49(d, J=2.3Hz, 1H), 3.47(q, J=7.1Hz, 4H), 2.22(s, 3H), 1.25(t, J=7.1Hz, 6H).

[0025] Weigh 3.01g (0.01mol) of yellow-brown crystals in a 100mL dry flask, dissolve in 20mL of dichloromethane, and add 4.26g (0.03mol) of boron trifluoride ether. Under the protection of nitrogen, t...

Embodiment 2

[0027] Preparation Ia:

[0028]

[0029] Weigh 0.35g (1mmol) of intermediate 1 in a 50mL flask, dissolve it in 10mL of acetic anhydride, add 0.402g (2mmol) of 1,3,3-trimethyl-2-methylene indoline acetaldehyde, at 60°C Reflux and stir for 3 h, TLC detects the reaction until the reaction is complete. After adding ice water, a solid precipitated out. After suction filtration, it was washed with perchloric acid and 5 mL of ethanol, and dried in vacuo to obtain 0.38 g of a dark blue solid with a yield of 57.5%. 1 H NMR (500MHz, DMSO) δ8.79(s, 1H), 8.39(d, J=15.6Hz, 2H), 7.82(d, J=10.3Hz, 2H), 7.79(d, J=7.4Hz, 2H ),7.71(d,J=7.9Hz,2H),7.55(t,J=7.7Hz,2H),7.46(t,J=7.4Hz,2H),7.07(d,J=15.6Hz,2H), 6.90(d,J=9.2Hz,1H),6.63(s,1H),3.89(s,6H),3.55(d,J=6.9Hz,4H),1.78(s,12H),1.17(t,J =6.9Hz,6H).

Embodiment 3

[0031] Prepare 10μmol / L Ia in different solvents, and test its ultraviolet-visible absorption spectrum and fluorescence emission spectrum.

[0032] The photophysical properties of the target molecule I in THF in the above examples are shown in Table 1:

[0033] Table 1: Photophysical properties of Ⅰ

[0034]

[0035] The results in Table 1 show that the maximum absorption wavelength of dye I in tetrahydrofuran is 617nm, and the maximum emission wavelength is 657nm. The strong molar absorptivity indicates the application prospect of compound I in the direction of luminescent materials, organic dyes and organic probes.

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Abstract

The invention discloses a synthetic method of a new cyanine, coumarin and difluoro boron hybrid dye with a fluorescent property, which has a general molecular formula shown in formula I. The dye is synthesized through design with the 7th site being a lignocaine electron-donating group and the 3rd site being a 6-methyl boron difluoride-beta-dicarbonyl hexatomic ring, wherein the methyl of the hexatomic ring is activated under the electrophilic effect and subjects to two times of Knoevenagel condensation with 1,3,3-trimethyl-2-methylene indoline acetaldehyde under different reaction conditions,the length of a conjugated chain is increased and a cyanine structure is introduced at the same time, so that the new cyanine, coumarin and difluoro boron hybrid dye I is formed. The synthetic methodis simple, and has wide application prospect in the fields such as fluorescence probes, life analysis and photoelectric materials.

Description

[0001] 【Technical field】 [0002] The invention synthesizes a novel fluorescent dye hybridized with cyanine, coumarin and dicarbonyl fluoride boron, and belongs to the field of novel hybrid fluorescent dye synthesis. [0003] 【Background technique】 [0004] In recent years, small molecule organic fluorescent materials have been widely used in the fields of luminescent materials, solar sensitized cells, and biological imaging. Common dye core structures are usually divided into coumarin dyes, cyanine dyes, BODIPY dyes, rhodamine dyes and benzothiadiazole dyes, etc., but each has its own disadvantages such as short absorption and emission wavelengths, Poor photostability, small Stokes shift, etc. [0005] The photophysical and photochemical properties of coumarin are stable, but its application range is limited due to its short absorption and emission wavelength (400-520nm), and research has found that the 7-position of its mother nucleus is introduced into an electron-donating ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09B23/10
CPCC07F5/022C09B23/107C09B23/0008
Inventor 胡志强王鲲鹏石广晋王硕陈绍晋张琦
Owner QINGDAO UNIV OF SCI & TECH
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