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Amphiphilic aza-BODIPY near-infrared dye and preparation method thereof

A technology of azafluoroborodipyrrole and near-infrared dyes, applied in azo dyes, organic dyes, chemical instruments and methods, etc., can solve the problems of short ultraviolet absorption wavelength of azafluoroborodipyrrole dyes, and achieve high photothermal Effects of conversion efficiency, structural stability, and simple reaction conditions

Pending Publication Date: 2021-04-02
TIANJIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the UV absorption wavelength of azafluoroboron dipyrrole dyes in the reports is relatively short, and there are no related reports that have high photothermal conversion efficiency after self-assembly in polar solvents such as water and methanol.

Method used

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  • Amphiphilic aza-BODIPY near-infrared dye and preparation method thereof
  • Amphiphilic aza-BODIPY near-infrared dye and preparation method thereof
  • Amphiphilic aza-BODIPY near-infrared dye and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] Example 1 (1,7-bis(p-dodecyloxy-phenyl)-3,5-bis(p-3,6,9,11-oxalkoxy-phenyl)azafluoroboron pyrrole)

[0067] Compound A1(C 36 h 54 o 7 )

[0068] 4-Dodecyloxybenzaldehyde (0.33mol, 1.1eq) was dissolved in 60mL of ethanol, and 18mL of KOH (0.18mol, 6eq) aqueous solution was added. Then p-3,6,9,11-oxaalkoxyacetophenone (0.03mol, 1eq) dissolved in ethanol (10mL) was added dropwise to the solution, and stirred at room temperature for 24h. The organic solvent was removed by rotary evaporation, dichloromethane was added to dissolve and washed three times with water, the obtained organic solvent was dried with anhydrous sodium sulfate, and the obtained filtrate was filtered to remove the organic solvent by rotary evaporation. The product was purified by silica gel column chromatography and Pet / EtOAc (1:1) to obtain the target product. 1H NMR (400MHz, CDCl3, ppm): δ=8.00(t, J=12.6Hz, 2H), 7.77(d, J=15.6Hz, 1H), 7.59(d, J=8.1Hz, 2H), 7.42( d,J=15.5Hz,1H),6.99(d,J=8.2Hz,2H)...

Embodiment 2

[0079] Example 2 (1,7-two (3,4-two-dodecyloxy-phenyl)-3,5-two (3,4-two-(4'-(N 1 -trioxadecyl)triazole-methoxy)-phenyl)azafluoroborondipyrrole)

[0080] Compound B1

[0081] Add compound 2 (5.5g, 1eq) to the flask, add 20ml of ethanol to dissolve, add KOH aqueous solution (6.17g, 4eq), drop the ethanol solution of compound 3 (13.04g, 1eq) into the flask, and heat up to 50°C Reaction 24h. Detection by thin layer chromatography. After the reaction, filter with suction and dry to obtain the target product. 1H NMR (400MHz, CDCl3) δ7.84–7.66(m,3H),7.35(d,J=15.5Hz,1H),7.21–7.07(m,3H),6.87(d,J=8.3Hz,1H) ,4.84(dd,J=4.0,2.4Hz,4H),4.03(dd,J=6.5,2.4Hz,4H),2.54(d,J=6.3Hz,2H),1.83(dd,J=12.7,7.2 Hz, 4H), 1.47(dd, J=11.5, 3.7Hz, 4H), 1.27(dd, J=16.9, 9.0Hz, 32H), 1.03–0.75(m, 6H). Figure 7 shown.

[0082]

[0083] Compound B2

[0084] Compound 3 (4.6g, 1eq) was dissolved in ethanol, CH3NO2 (2.1g, 5eq) and sodium ethoxide in ethanol (0.06g, 0.1eq) were added to react at 82°C for 12...

Embodiment 3

[0095] Example 3 (1,7-two (3,4,5-three-dodecyloxy-phenyl)-3,5-two (3,4,5-three-(4'-(N 1 -dioxaheptayl)triazole-methoxy)-phenyl)azafluoroborondipyrrole)

[0096] Compound C1(C 60 h 90 o 7 )

[0097]Synthesis of 3',4',5'-tris(propynyloxy)-3,4,5,-tris(dodecyloxy)-chalcone (C30H38O3): 3,4,5-tripropane Dissolve 15mmol of alkynyloxyacetophenone in a mixed solution of 50ml of ethanol containing 60mmol of potassium hydroxide and 15ml of water, stir for 30min, and slowly drop the ethanol solution containing 15mmol of 3,4,5-tris(dodecyloxy)benzaldehyde Add, react at room temperature for 12h, filter to obtain the precipitate, wash with water to neutral pH, and obtain a white powdery solid. 1H NMR: (400MHz, CDCl3): 8.05(d, J=8.8Hz, 2H), 7.80(d, J=15.6Hz, 1H), 7.60(d, J=8.5Hz, 2H), 7.44(d, J =15.6Hz,1H),7.07(d,J=8.7Hz,2H),6.93(d,J=8.6Hz,2H),4.78(d,J=2.1Hz,2H),3.99(t,2H), 2.56(s,1H)1.80(m,2H),1.46-1.27(m,18H),0.90(t,3H). Figure 13 shown.

[0098]

[0099] Compound C4(C 122 h ...

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Abstract

The invention relates to an amphiphilic aza-BODIPY near-infrared dye and a preparation method thereof; through molecular design, hydrophilic chain oligomeric glycol ether groups and hydrophobic chaindodecyloxy group chains with different numbers and positions are connected into 1,3,5,7-tetramethyl aza-BODIPY derivatives to regulate aza-BODIPY properties so as to research aza-BODIPY self-assemblybehaviors, and the photothermal property provides an effective synthesis method guarantee. The method has the advantages of few synthesis steps, simple reaction conditions, high product yield and stable structure. Ultraviolet absorption is carried out at 705-7XX nm in a dichloromethane solution, and red shift of ultraviolet absorption in a polar solvent is carried out to 809-8XX nm. The self-assembly has regular morphology, is expected to have high photo-thermal conversion efficiency under the action of proper near-infrared laser, and has potential application prospect as a new photo-thermal reagent.

Description

technical field [0001] The invention relates to the technical field of a dye preparation method, in particular to a class of amphiphilic azafluoroboron-dipyrrole near-infrared dyes and a preparation method thereof. Background technique [0002] Hyperthermia (Photo-thermal Therapy, PTT) is to change the environment of tumor cells by heating to make tumor cells degenerate and necrosis, so as to achieve the purpose of treatment [Small., 2011, 7, 169-183], near infrared region (780 -1100nm) is the transmission window of body tissue, and near-infrared light has the highest transmittance in body tissue, and has the least damage to the human body compared with other wavelengths of light. Compared with traditional small-molecule drugs used in tumor chemotherapy, near-infrared photothermal induction has the characteristics of low toxicity and high therapeutic specificity, because the settings of near-infrared irradiation are controllable, such as exposure time, position of laser sour...

Claims

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Application Information

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IPC IPC(8): C07F5/02C09B57/00C09K11/06
CPCC07F5/02C09B57/00C09K11/06C09K2211/107C09K2211/1059
Inventor 陈志坚田丹丹潘宏斐郭平平
Owner TIANJIN UNIV
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