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Phenothiazine-containing pillararene fluorescent adsorption material and preparation method thereof

An adsorption material, phenothiazine technology, applied in the field of phenothiazine-containing columnarene fluorescent adsorption material and its preparation, can solve the difficulty of purification and separation, limit the research and application of columnarene and its derivatives, and it is difficult to obtain compact and rigid crystals and other issues

Active Publication Date: 2021-08-03
EAST CHINA UNIV OF SCI & TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, pillararene itself has no fluorescence, and it is difficult to judge the adsorption situation by simple observation in practical applications.
The method of linking fluorescent molecules through alkyl chains, for simple small molecules such as halogenated hydrocarbons, alkanes, and aromatic hydrocarbons, it is impossible to judge whether there is a combination, and it is difficult to obtain compact and rigid crystals, which limits the further application of such molecules
For pillararenes with fluorescent units in the parent structure, the change of the cavity during the adsorption process of pillararenes can be judged simply and directly, but the synthesis method is often tedious and cumbersome, and the purification and separation are difficult, which limits the research on pillararenes and their derivatives. Research and Application

Method used

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  • Phenothiazine-containing pillararene fluorescent adsorption material and preparation method thereof
  • Phenothiazine-containing pillararene fluorescent adsorption material and preparation method thereof
  • Phenothiazine-containing pillararene fluorescent adsorption material and preparation method thereof

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preparation example Construction

[0051] The preparation method of compound 6 comprises the following steps:

[0052](1) Compound 1 (21.0 g, 0.15 mol) (1,4-dimethoxybenzene, purchased from Adamas, specification 500 g, purity 99%) was dissolved in dichloroethane (600 mL) at room temperature, Add paraformaldehyde (9.0g, 0.30mmol) and trifluoroacetic acid (30mL) to the solution, and stir at reflux for 5h to obtain compound 2; wherein, the volume ratio of dichloromethane and trifluoroacetic acid is 20:1, compound 1 and poly The molar ratio of polyoxymethylene is 1:2.

[0053] (2) At room temperature, compound 2 (7.000g, 9.30mmol) was dissolved in a mixture of dichloromethane (350mL) and tetrahydrofuran (350mL), and ceric ammonium nitrate (11.235g, 20.5mmol) was added dropwise to the solution ) aqueous solution (42mL), after dropping, stirred for 24h to obtain compound 3; wherein, the volume ratio of dichloromethane and tetrahydrofuran was 1:1, and the molar ratio of compound 2 and ceric ammonium nitrate was 1:2.2...

Embodiment 1

[0058]

[0059] In the glove box, under argon atmosphere, compound 6 (414mg, 0.5mmol), sodium tert-butoxide (170mg, 1.5mmol), palladium acetate (5mg, 0.01mmol), tri-tert-butylphosphine tetrafluoroborate (12mg, 0.02mmol), 2-bromo-9-fluorenone (259mg, 1.0mmol) and toluene (3mL) were mixed at a temperature of 100-110°C and stirred for 23h under an argon atmosphere. The reaction solution was cooled to room temperature, 50 mL of water was added, extracted with dichloromethane (50 mL×3), the organic phases were combined, dried over sodium sulfate, and purified by column chromatography to obtain 327 mg of compound 7 with a yield of 65.0%.

[0060] figure 1 Compound 7 prepared for Example 1 of the present invention 1 H-NMR diagram, 1 H NMR (400MHz, CDCl 3 )δ=7.69(d, J=8.0Hz, 1H), 7.59(d, J=8.0Hz, 1H), 7.56(d, J=4.0Hz, 1H), 7.44(t, J=8.0Hz, 1H) ,7.32-7.40(m,3H),7.27(t,J=6.0Hz,1H),7.21(d,J=6.0Hz,1H),7.14(t,J=8.0Hz,1H),7.04(s, 2H), 7.01(s, 1H), 6.85(m, 2H), 6.75(m, 1H), 6.54-6.70...

Embodiment 2

[0065]

[0066] In the glove box, under argon atmosphere, compound 6 (455.4mg, 0.55mmol), sodium tert-butoxide (187mg, 1.65mmol), palladium acetate (5mg, 0.01mmol), tri-tert-butylphosphine tetrafluoroboric acid Salt (12mg, 0.02mmol), 2-bromoanthracene (257mg, 1.0mmol) and toluene (3.2mL) were mixed at 100-110°C and stirred for 22h under an argon atmosphere. The reaction solution was cooled to room temperature, 50 mL of water was added, extracted with dichloromethane (50 mL×3), the organic phases were combined, dried over sodium sulfate, and purified by column chromatography to obtain 338 mg of compound 9 with a yield of 61.2%.

[0067] image 3 For the compound 9 prepared by the embodiment of the present invention 2 1 H-NMR diagram, 1 H NMR (400MHz, CDCl 3 )δ=8.24(s,1H),8.06(s,1H),7.88(d,J=8.0Hz,1H),7.82(d,J=8.0Hz,1H),7.79(d,J=4.0Hz, 1H), 7.77(d, J=4.0Hz, 1H), 7.59(d, J=8.0Hz, 1H), 7.45(t, J=8.0Hz, 1H), 7.34-6.24(m, 4H), 7.10( d,J=4.0Hz,J=8.0Hz,1H),7.07(s,1H),7.00(d,J=...

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Abstract

The invention discloses a phenothiazine-containing pillararene fluorescent adsorption material and a preparation method thereof. The structural general formula of the phenothiazine-containing pillararene fluorescent adsorption material is shown in the specification. The phenothiazine-containing pillararene fluorescent adsorption material disclosed by the invention is reasonable in molecular design, a synthesized target object is novel, and organic matter with similar structures can be specifically detected, adsorbed and separated; and the process can be monitored through the change of material fluorescence. The molecules are good in solubility, simple to synthesize and purify and variable in molecular structure, the synthesis method has universality, and functional compounds with different structures and properties can be conveniently designed according to needs.

Description

technical field [0001] The invention belongs to the technical field of organic chemical synthesis, and in particular relates to a class of phenothiazine-containing columnarene fluorescent adsorption materials and a preparation method thereof. Background technique [0002] Pillararenes and their derivatives are a new class of macrocyclic compounds with high symmetry and rigidity. Compared with traditional macrocycles such as cucurbituril and cyclodextrin, they are easier to be modified because of their strong resistance to halogenated hydrocarbons, alkanes, aromatic hydrocarbons, etc. The compound has good selective adsorption and is considered to be a very potential small molecule adsorption material. However, pillararene itself has no fluorescence, and it is difficult to judge the adsorption situation by simple observation in practical applications. For simple small molecules such as halogenated hydrocarbons, alkanes, and aromatic hydrocarbons, it is impossible to determin...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D279/14C07D417/04C09K9/02C09K11/06G01N21/64B01J20/22B01J20/30
CPCC07D279/14C07D417/04C09K9/02C09K11/06B01J20/22G01N21/6428C09K2211/1037C09K2211/1029C09K2211/1011Y02E10/549
Inventor 曲大辉金苇航王骞王梦奇
Owner EAST CHINA UNIV OF SCI & TECH
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