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Polybrominated diphenyl ethylene dye sensitizing agent, synthesis and use thereof

A technology of polybrominated stilbenes and dye sensitizers, applied in the preparation of styrene-based dyes and organic compounds, and the preparation of amino compounds from amines, etc., can solve the problems of poor singlet oxygen quantum yield, etc. Achieve the effects of convenient and easy-to-obtain raw material sources, wide coverage, and high quantum yield of singlet oxygen

Inactive Publication Date: 2009-05-27
CHONGQING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The sensitizers currently used for singlet oxygen are all common compounds that absorb near-ultraviolet light and visible light, such as porphyrin, etc. Due to the limitation of the excited state properties, the main reason is that the coefficient of intersystem crossing can be adjusted to make them optically The quantum yield of induced singlet oxygen is not very good

Method used

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  • Polybrominated diphenyl ethylene dye sensitizing agent, synthesis and use thereof
  • Polybrominated diphenyl ethylene dye sensitizing agent, synthesis and use thereof
  • Polybrominated diphenyl ethylene dye sensitizing agent, synthesis and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Synthesis of p-N, N-diphenyl-pentabromostilbene

[0038] The synthesis proceeds in three steps:

[0039] (1) Synthesis of brominated pentabromotoluene

[0040] 10 grams of pentabromotoluene and 3.7 grams of NBS (molar ratio 1:1) are mixed in a three-necked ground flask, and a condensing device is added, and in CCl 4 Reflux for 48 hours, filter, recrystallize the solid in benzene / cyclohexane, filter to obtain crystals, the yield is 75%, and set aside;

[0041] (2) Esterification of pentabromotoluene

[0042] Mix 5 grams of bromopentabromotoluene synthesized in the first step with 4.5 grams of triethyl phosphite (molar ratio 1:5) in a three-necked flask, stir at 130-160°C for 6 hours, and evaporate excess The triethyl phosphite, obtains white crystal, productive rate 95%, for subsequent use;

[0043] (3) Synthesis of p-N, N-diphenyl-pentabromostilbene

[0044] Pentabromotoluene and 1.74 gram p-N, N-diphenyl-benzaldehyde (molar ratio 1:1.2) after the 3.3 gram esterifi...

Embodiment 2

[0046] Synthesis of 3,4,5-trimethoxy-pentabromostilbene

[0047] The synthesis proceeds in three steps:

[0048] (1) Synthesis of brominated pentabromotoluene

[0049] Synthesis is by the first step in embodiment 1;

[0050] (2) Esterification of pentabromotoluene

[0051] Synthesis is by the second step in Example 1;

[0052] (3) Synthesis of 3,4,5-trimethoxy-pentabromostilbene

[0053] Pentabromotoluene and 0.83 gram 3,4,5-trimethoxyl-benzaldehyde (molar ratio 1:1.2) mixed with the 2.2 gram esterified pentabromotoluenes that the second step makes are added in the three-necked ground-necked flask, add Condenser, then dissolve with 200ml of dry tetrahydrofuran solvent, add 0.73 gram of sodium methylate, reflux for 12 hours, filter the precipitate after cooling, after the solvent in the filtrate is spin-dried in vacuum, adopt silica gel column separation to obtain the compound of the invention, the yield 38%.

Embodiment 3

[0055] Will 1×10 -5 The p-N of mol / L, N-diphenyl-pentabromostilbene is dissolved in methylene chloride, and its ultraviolet-visible absorption spectrum is measured, as figure 1 .

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Abstract

Singlet state oxygen produced through photosensitization has important application from photobiology to polymer science. The invention relates to a sensitizing agent for producing the singlet state oxygen based on polybrominated dye and synthesis and application thereof, which belong to the filed of organic dye; and the general formula of a typical chemical structure of a compound is shown as a figure, wherein in the molecular structural formulas (I) (II), R represents methyl, ethyl, propyl, butyl, pentyl, hexyl, benzyl and other groups. The product obtained through the reaction of pentabromodiphenyl bromo-toluene and triethyl phosphate and an aldehydic benzene substituting substance react in a glass vessel under the alkali condition to prepare the polybrominated dye; and the polybrominated dye can be sensitized to produce the singlet state oxygen under irradiation of near ultraviolet light and visible light.

Description

technical field [0001] The invention belongs to the field of singlet oxygen sensitizers, in particular to the synthesis and application of a class of polybrominated stilbene dyes. Background technique [0002] Since the discovery of singlet oxygen in 1960, the research on the chemistry and biochemistry of singlet oxygen has received great attention, such as photosensitive oxidation of organic molecules, photodegradation of polymers and many other research work involving singlet oxygen. Compared with ground state oxygen, singlet oxygen can selectively react with many electron-rich molecules, and the products can be used as materials or intermediates in drug synthesis. In particular, singlet oxygen plays an important role in biological processes and can be used for photodynamic therapy. The sensitizers currently used for singlet oxygen are all common compounds that absorb near-ultraviolet light and visible light, such as porphyrin, etc. Due to the limitation of the excited st...

Claims

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Application Information

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IPC IPC(8): C07C211/52C07C209/68C07C43/225C07C41/30C09B23/14
Inventor 高放郭钦园谢亭胡女丹李红茹张胜涛
Owner CHONGQING UNIV
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