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Long wavelength boron dipyrromethene dye and preparation thereof

A technology of fluoroboridipyrrole and long wavelength, which is applied in the field of preparation of long-wavelength fluoroboridipyrrole dyes and their derivatives, and can solve problems such as large application potential, insufficient properties of target compounds, and difficult synthesis

Inactive Publication Date: 2008-11-12
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Some literature reports (Eur.J.Org.Chem 2006,4658-4663; Chem.Commun.2006,266-268; Chem-Eur.J.2003,4430-4441; Tetrahedron2006,8484-8488; Angew. Chem.Int.Ed.2001, 385-387) introduces conjugated groups on the fluoroborate dipyrrole parent to expand the conjugated system, but there are still some problems, such as synthesis difficulties, the properties of the target compound are not good enough, etc., However, its application potential is great, so there are still many people engaged in research in this area.

Method used

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  • Long wavelength boron dipyrromethene dye and preparation thereof
  • Long wavelength boron dipyrromethene dye and preparation thereof
  • Long wavelength boron dipyrromethene dye and preparation thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040]

[0041] Add 0.51 mmol of dibromo-substituted fluoroborate dipyrrole, 3 times the molar amount of styrene boronic acid, 40 mL of N, N-dimethylformamide to a 100 mL two-necked bottle, keep the system at 50 ° C under stirring, react for 8 h, and pass through a silica gel column to obtain Blue-purple solid, yield 80%, HRMS[M] + : 466.2393(m / z); 1 H-NMR (400Mz, CDCl3): δ=1.37(s, 6H), 1.70(s, 3H), 2.56(s, 6H), 6.65(d, 2H), 6.84(d, 2H) 7.21-7.30(m ,10H); 13 C-NMR (100MHz, CDCl 3 ): δ=14.0, 16.4, 20.8, 106.0, 112.0, 121.8, 122.6, 125.7, 126.5, 127.6, 128.7, 129.5, 130.6, 148.7.

[0042] figure 1 , 2 Spectral data for this product are given. figure 1 It is the absorption spectrogram of product, and ordinate represents relative intensity, and abscissa represents wavelength, and the maximum absorption wavelength of this product is 574 nanometers. figure 2 is the fluorescence emission spectrum diagram of the product, the ordinate represents the relative intensity, and t...

Embodiment 2

[0044]

[0045] Add 0.51mmol monobromofluoroborate dipyrrole, 2.5 times the molar amount of p-methoxystyrene boronic acid, 40mL dimethyl sulfoxide to a 100mL two-necked bottle, keep the system at 60°C under stirring, react for 15h, pass through a silica gel column, A purple solid was obtained, the yield was 75%, HRMS[M] + : 456.2185(m / z); 1 H-NMR (400Mz, CDCl3): δ=1.37(s, 3H), 1.57(s, 3H), 2.26(s, 3H), 2.56(s, 3H), 3.06(s, 3H), 6.0(s, 1H), 6.63(d, 1H), 6.83(d, 1H), 7.14-7.30(m, 9H); 13 C-NMR (100MHz, CDCl 3 ):

[0046] δ=12.0, 14.4, 20.8, 25.7, 60.4, 109.0, 112.8, 116.6, 118.7, 120.1, 121.5, 122.2, 123.0, 125.4, 126.8, 127.7, 128.6, 129.4, 130.8, 131.5, 138, 139.0, 1395 140.7, 142.6.

Embodiment 3

[0048]

[0049] Add 0.51 mmol of bis-bromofluoroborate dipyrrole, 3.5 times the molar amount of hexene boronic acid, and 40 mL of 1,4-dioxane to a 100 mL two-necked bottle, keep the system at 70 ° C under stirring, react for 18 h, and pass through a silica gel column to obtain Blue-purple solid, yield 72%, HRMS[M] + : 560.3386(m / z); 1 H-NMR (400Mz, CDCl3): δ=0.8-1.2 (m, 22H), 1.57 (s, 6H), 2.56 (s, 6H), 3.06 (s, 3H), 6.0 (s, 1H), 6.63 ( d, 1H), 6.83 (d, 1H), 7.14-7.30 (m, 4H), 10.42 (s, 1H).

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Abstract

The invention provides a preparation method of a long wavelength BODIPY dye and a derivative thereof, belonging to the organic chemical industry and the fine chemical industry technology field. Bromine or iodo-BODIPY and substituted alenyle boric acid are used as the raw material with the mol ratio around 1 to between 2 and 10 in the preparation method of the long wavelength BODIPY dye and the derivative thereof, palladium carbon or zero-valent palladium is used as a catalyst, the mol ratio of bromine or iodo-BODIPY to the catalyst is 1 to between 0.01 and 0.20. Allowing the bromine or iodo-BODIPY and the substituted alenyle boric as well as the catalyst to react in an organic solvent for one to seventy-two hours at a temperature of between forty and one hundred and sixty DEG C with the protection and stirring of argon or nitrogen, then the bromine or iodine on the raw material is substituted, conjugated double bond BODIPY derivative is generated and the boric acid and conjugated double bond BODIPY derivative is substituted, and after the introduction of conjugated double bond groups in different numbers, the optical property of the BODIPY is changed to absorb and emit spectrum and Einstein shift occurs.

Description

technical field [0001] The invention relates to a preparation method of a class of long-wavelength fluoroborate dipyrrole dyes and derivatives thereof, and belongs to the technical fields of organic chemical industry and fine chemical industry. Background technique [0002] Fluoroboron dipyrrole dyes are a kind of commonly used dye precursors, and their structures are shown in the figure below. [0003] [0004] It is a very important compound in organic dyes. At the same time, the large π-π conjugated system in its molecular structure endows it with excellent fluorescence and photoelectric properties, such as high molar extinction coefficient, high quantum yield, and better Photochemical stability and other properties make its derivatives have applications in biological probes, solar cells, lasers and other fields. Especially the research of this kind of dye in the biological field has become one of the hotspots of people's research now. Some literature reports (Eur.J....

Claims

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Application Information

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IPC IPC(8): C09B57/00
Inventor 肖义张大奎
Owner DALIAN UNIV OF TECH
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