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2,6-diiodo-BODIPY derivative and preparation method and application thereof

A derivative, diiodo technology, applied in the field of 2,6-diiodo BODIPY derivatives and its preparation, can solve the problems of incompatibility, complicated operation, low yield, etc., and achieve enhanced crossover efficiency and easy modification , The effect of improving photodynamic properties

Active Publication Date: 2018-11-27
SHANDONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the classic synthesis method of BODIPY is based on the condensation reaction of benzaldehyde and pyrrole, which has low yield, difficult separation, complicated operation, and even incompatibility with some active functional groups (such as amino, iodine, etc.), which greatly limits the research and development of BODIPY. application

Method used

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  • 2,6-diiodo-BODIPY derivative and preparation method and application thereof
  • 2,6-diiodo-BODIPY derivative and preparation method and application thereof
  • 2,6-diiodo-BODIPY derivative and preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] (a) Synthesis of compound (I)

[0051] 4-Nitrobenzoyl chloride (1.0g) and 2,4-dimethylpyrrole (1.0g) were dissolved in dichloromethane (25mL), and heated at 45°C for 1h. Triethylamine (2.5 mL) was added and heating was continued at 45°C for 15 min. Boron trifluoride diethyl etherate (2.5 mL) was added and heated at 45° C. for 3 h. The mixture was evaporated to remove the solvent, and then separated by neutral alumina column chromatography with dichloromethane as the eluent. Purple-red solid, yield 0.8g, yield 40%

[0052] 1 H NMR (400MHz, CDCl 3 )δ8.39(d, J=8.7Hz, 2H), 7.54(d, J=8.7Hz, 2H), 6.02(s, 2H), 2.57(s, 6H), 1.36(s, 6H).

[0053] 13 C NMR (101MHz, CDCl 3 )δ156.69, 148.35, 142.54, 141.96, 138.34, 130.64, 129.66, 124.37, 121.86, 14.70, 14.67.

[0054] MALDI-TOF MS, Calcd. For[M], 369.146, Found, 369.703.

[0055] Anal. Calcd. For C 19 h 18 BF 2 N 3 o 2 (%): C, 61.82; H, 4.91; N, 11.38, Found: C, 61.65; H, 5.00; N, 11.28.

[0056] (b) Synthesis of co...

Embodiment 2

[0082] Surface Modification of COF LZU-1 by Compound III

[0083] Dissolve compound III (10.6 mg) in ethanol (5 mL), add COF LZU-1 (5 mg), and disperse uniformly by ultrasonic; then add aqueous acetic acid (50 μL, 3 mol / L), transfer to a polytetrafluoroethylene reactor, 75 ℃ insulation 4h. After cooling, centrifuge at 12000rpm for 30min, wash the precipitate with ethanol until the supernatant is colorless, then wash once with ether, and dry at 40°C to obtain orange-yellow powder COFLZU-1-BODIPY-2I.

[0084]The COF LZU-1 was prepared as follows: Trimylene (20 mg), p-phenylenediamine (20 mg), and trifluoroacetic acid (720 μL) were dissolved in ethanol (8 mL) to obtain a dark red solution. Transfer to a polytetrafluoroethylene reactor and keep warm at 120°C for 12h. After cooling, centrifuge at 12000rpm for 30min, wash the precipitate twice with ethanol+triethylamine (v / v=16:1) solution, then wash once with ether, and dry at 40°C to obtain a brownish yellow powder.

[0085] Th...

Embodiment 3

[0092] Heavy-atom-enhanced photodynamic performance

[0093] The COF LZU-1-BODIPY-2I was dispersed in phosphate saline buffer solution (PBS), and its photodynamic performance was evaluated by the specific singlet oxygen scavenger DPBF.

[0094] Take COF LZU-1-BODIPY-2I PBS dispersion (2mL, the concentration is 10μmol / L according to BODIPY), add DPBF / DMF solution (1mmol / L, 100μL), and use a green LED lamp (power density 40mW / cm 2 ) for different time, monitor the UV-Vis spectrum of DPBF ( Figure 14 ). The same method was used to evaluate the photodynamic performance of COF LZU-1-BODIPY with the same concentration ( Figure 15 ). And take the maximum absorption peak absorbance A of DPBF and the initial absorbance A 0 The ratio of A / A 0 is the ordinate, and the illumination time is plotted as the abscissa ( Figure 16 ).

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Abstract

The invention relates to the technical field of organic synthetic chemistry, in particular to a 2,6-diiodo-BODIPY derivative and a preparation method and application thereof. A compound (III) can react with various nano materials (such as a metal organic framework material, a covalent organic framework material and the like) to achieve the surface modification of the nano materials and impart newfunctions to the nano materials; in addition, the intersystem crossing efficiency of the molecules of the compound is greatly increased, so that the photodynamic performance of BODIPY is greatly improved, and the compound (III) has good characteristics of being expanded and modified easily. The 2,6-diiodo-BODIPY derivative and the preparation method and application thereof have the advantages thatan effective reducing agent is selected, and a corresponding reaction condition is set, so that the compound (III) can be obtained through the reaction of a compound (II), and the yield reaches up to42%. The invention also provides the application of the compound (III) in the nano material modification.

Description

technical field [0001] The invention relates to the technical field of organic synthesis chemistry, in particular to a 2,6-diiodo-BODIPY derivative and its preparation method and application. Background technique [0002] 4-bora-3a,4a-diaza-4,4-difluoro-s-indacene, commonly known as BODIPY, has a sharp UV absorption peak, a large molar absorptivity, and a high fluorescence quantum yield. Almost independent of solvent polarity and pH. This makes BODIPY widely used as a fluorescent dye in living cells and a fluorescent labeling reagent for biomacromolecules. The 2,6-position of BODIPY can conveniently introduce iodine atoms through nucleophilic substitution reactions, and enhance intersystem crossing through the heavy atom effect, thereby increasing the lifetime of the triplet state, making BODIPY promising as a photosensitizer for photodynamic therapy. [0003] By modifying the BODIPY core, the fluorescent properties of BODIPY can be optimized and active sites can be provid...

Claims

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Application Information

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IPC IPC(8): C07F5/02C09K11/06C08G83/00A61K41/00
CPCA61K41/0057C07F5/022C08G83/008C09K11/06C09K2211/1007C09K2211/1029C09K2211/1055
Inventor 董育斌官群李延安
Owner SHANDONG NORMAL UNIV
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