CN105884585A - Method for preparing calix[4]arene fluorescent dye with solid light emission property - Google Patents
Method for preparing calix[4]arene fluorescent dye with solid light emission property Download PDFInfo
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- CN105884585A CN105884585A CN201610315965.9A CN201610315965A CN105884585A CN 105884585 A CN105884585 A CN 105884585A CN 201610315965 A CN201610315965 A CN 201610315965A CN 105884585 A CN105884585 A CN 105884585A
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- benzophenone
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/30—Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
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- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention belongs to the technical field of organic compound preparation, and relates to a method for preparing a calix[4]arene fluorescent dye with a solid light emission property. The preparation mechanism comprises the following steps: converting bridge methylene in calix[4]arene into lithium salt by using n-butyllithium, adding benzophenone to react, and dehydrating a reaction product under the catalysis of p-toluenesulfonic acid, thereby obtaining benzhydrylidene substituted calix[4]arene. Due to a tetraphenyl ethylene structure unit in the compound, the dye has the property of solid light emission.
Description
Technical field
The invention belongs to organic compound preparation technical field, be specifically related to a kind of cup [4] with solid luminescent character
The preparation method of aromatic hydrocarbons fluorescent dye.
Background technology
Calixarenes generally refers to the macrocyclic compound being made up of methylene-bridged phenol units, and because of it, to have size adjustable
The cavity of joint, it is possible to form Host-guest Complexes, be referred to as the third generation host compound after crown ether and cyclodextrin.Cause
In the phenolic hydroxyl group of calixarenes lower edge, the phenolic hydroxyl group contraposition of upper limb, and the methylene of benzene ring units can be connected for this compounds
Base can carry out various selectively functionalized so that it is tool has been widely used, and e.g., ionophore, ion transducer, phase transfer is urged
Agent, catalyst etc..But as fluorescent dye, current report is all by introducing it by the upper and lower edge at calixarenes
He the method for fluorescence molecule realizes, and utilizes the skeleton preparation of calixarenes to have the calixarenes fluorescent dye of solid luminescent character
Method does not also have.
Summary of the invention
Present invention solves the technical problem that and be, utilize the methylene bridge on the skeleton of cup [4] aromatic hydrocarbons and phenol units, logical
Cross 1, the introducing of 1-diphenyl methylene, build a tetraphenyl ethylene unit, because tetraphenyl ethylene molecule has assembles luminous property
Matter, we can provide a kind of method prepared and have cup [4] aromatic hydrocarbons assembling luminosity.
The technical scheme is that, diphenyl methylene replaces the preparation method of cup [4] aromatic hydrocarbons, is mainly characterized by warp successively
Cross following steps:
Under nitrogen protection, by 5,11,17,23-tetra-tert-25,26,27,28-tetramethoxy cup [4] aromatic hydrocarbons are dissolved in tetrahydrochysene
In furans, it is cooled to-10-0oC, joins in mixture by the hexane solution of n-BuLi, and nitrogen is protected, stirring, reaction
After 1 hour, add 4-methyldiphenyl ketone, the 5 of the most every 1 mM, 11,17,23-tetra-tert-25,26,27,28-tetramethyls
Epoxide cup [4] aromatic hydrocarbons adds 10-20 milliliter oxolane, 4.5 mMs of n-BuLis, 8-10 mM of benzophenone, adds
After, temperature being risen to 40-70 DEG C, continues reaction 12-36 hour, the ammonium chloride solution adding 10% makes reaction stop, and reaction is mixed
Compound dichloromethane extracts, the organic phase saturated aqueous common salt washing obtained, and is dried, removes solvent, obtain in the middle of tertiary alcohol
Product, is placed in this intermediate product in the flask with Dean-Stark water knockout drum, add toluene, p-methyl benzenesulfonic acid, wherein than
Example relation is that every mM of intermediate product alcohol adds 20-50 milliliter toluene, 0.1-0.2 mM of p-methyl benzenesulfonic acid, is heated to 140
DEG C, to react 4-6 hour, point water, after having reacted, add the sodium bicarbonate solution washing of 10%, be dried, remove solvent, use contains
The n-hexane of ethyl acetate 0.5-2% carries out column chromatography mutually as flowing, obtains white solid.
Heretofore described benzophenone is selected from benzophenone, 4-bromine benzophenone, 4-methyl benzophenone, 4-first
Epoxide benzophenone, 4,4 '-dibromobenzo-phenone, 4,4 '-dimethyl benzophenone, 4,4 '-dimethoxy-benzophenone, in
One.
The mechanism of preparation method of the present invention is as follows:
Except the hydrogen atom in methylene bridge in 5,11,17,23-tetra-tert-25,26,27,28-tetramethoxy cup [4] aromatic hydrocarbons
Not having outward other reactive hydrogen atoms, we use butyl lithium and the atomic reaction of hydrogen in methylene bridge, by calixarenes lithium salts, its
Carrying out nucleophilic addition with benzophenone further and obtain tertiary alcohol intermediate product, this alcohol is dehydrated under Catalyzed by p-Toluenesulfonic Acid
Obtain diphenyl methylene substituted cup [4] aromatic hydrocarbons.
Under chemical reaction formula:
The present invention designs and synthesizes a kind of diphenyl methylene with solid luminescent character and has replaced the preparation method of calixarenes.
Accompanying drawing explanation
Fig. 1 is the chemical equation that diphenyl methylene replaces cup [4] aromatic hydrocarbons.
Detailed description of the invention
Below in conjunction with specific embodiment, the present invention is further detailed explanation.
Embodiment one
Diphenyl methylene replaces the synthesis of cup [4] aromatic compound 1
(1) by 5,11,17,23-tetra-tert-25,26,27,28-tetramethoxy cup [4] aromatic hydrocarbons (1.41 g, 2 mmol) are put
In 50 mL reactors；
(2) oxolane that 20 mL are dried is added under nitrogen protection；
(3) it is cooled to-5 DEG C；
(4) 3.6 mL(9 mmol are added) n-BuLi hexane solution (2.5 mol/L), reacts 1 hour；
(5) benzophenone (2.92 g, 16 mmol) is added in mixed solution；
(6) reaction temperature is risen to 70 DEG C, continue reaction 24 hours；
(7) ammonium chloride solution adding 10% makes reaction stop；
(8) extract (3 × 50 mL) with dichloromethane, merge organic phase, wash with saturated aqueous common salt；
(9) use anhydrous magnesium sulfate to be removed by solvent after drying, obtain tertiary alcohol intermediate product；
(10) it is placed in obtaining intermediate product in the 150 mL round-bottomed flasks with Dean-Stark hydrophone, adds 80 mL toluene；
(11) p-methyl benzenesulfonic acid (57 mg, 0.3 mmol) is added；
(12) reactant is heated at 140 DEG C, react 4 hours；
(13), after having reacted, add the sodium bicarbonate solution washing of 10%, be dried, remove solvent；
(14) use the n-hexane containing ethyl acetate 0.5% to carry out column chromatography mutually as flowing, obtain white solid, productivity 73%.
Embodiment two
Diphenyl methylene replaces the synthesis of cup [4] aromatic compound 2
(1) by 5,11,17,23-tetra-tert-25,26,27,28-tetramethoxy cup [4] aromatic hydrocarbons (1.41 g, 2 mmol) are put
In 50 mL reactors；
(2) oxolane that 20 mL are dried is added under nitrogen protection；
(3) it is cooled to-5 DEG C；
(4) 3.6 mL(9 mmol are added) n-BuLi hexane solution (2.5 mol/L), reacts 1 hour；
(5) 4-methyl benzophenone (3.14 g, 16 mmol) is added in mixed solution；
(6) reaction temperature is risen to 70 DEG C, continue reaction 24 hours；
(7) ammonium chloride solution adding 10% makes reaction stop；
(8) extract (3 × 50 mL) with dichloromethane, merge organic phase, wash with saturated aqueous common salt；
(9) use anhydrous magnesium sulfate to be removed by solvent after drying, obtain tertiary alcohol intermediate product；
(10) it is placed in obtaining intermediate product in the 150 mL round-bottomed flasks with Dean-Stark hydrophone, adds 80 mL toluene；
(11) p-methyl benzenesulfonic acid (57 mg, 0.3 mmol) is added；
(12) reactant is heated at 140 DEG C, react 4 hours；
(13), after having reacted, add the sodium bicarbonate solution washing of 10%, be dried, remove solvent；
(14) use the n-hexane containing ethyl acetate 0.5% to carry out column chromatography mutually as flowing, obtain white solid, productivity 78%.
Embodiment three
Diphenyl methylene replaces the synthesis of cup [4] aromatic compound 3
(1) by 5,11,17,23-tetra-tert-25,26,27,28-tetramethoxy cup [4] aromatic hydrocarbons (1.41 g, 2 mmol) are put
In 50 mL reactors；
(2) oxolane that 20 mL are dried is added under nitrogen protection；
(3) it is cooled to-5 DEG C；
(4) 3.6 mL(9 mmol are added) n-BuLi hexane solution (2.5 mol/L), reacts 1 hour；
(5) 4-bromine benzophenone (4.18 g, 16 mmol) is added in mixed solution；
(6) reaction temperature is risen to 70 DEG C, continue reaction 24 hours；
(7) ammonium chloride solution adding 10% makes reaction stop；
(8) extract (3 × 50 mL) with dichloromethane, merge organic phase, wash with saturated aqueous common salt；
(9) use anhydrous magnesium sulfate to be removed by solvent after drying, obtain tertiary alcohol intermediate product；
(10) it is placed in obtaining intermediate product in the 150 mL round-bottomed flasks with Dean-Stark hydrophone, adds 80 mL toluene；
(11) p-methyl benzenesulfonic acid (57 mg, 0.3 mmol) is added；
(12) reactant is heated at 140 DEG C, react 4 hours；
(13), after having reacted, add the sodium bicarbonate solution washing of 10%, be dried, remove solvent；
(14) use the n-hexane containing ethyl acetate 0.5% to carry out column chromatography mutually as flowing, obtain white solid, productivity 70%.
Embodiment four
Diphenyl methylene replaces the synthesis of cup [4] aromatic compound 4
(1) by 5,11,17,23-tetra-tert-25,26,27,28-tetramethoxy cup [4] aromatic hydrocarbons (1.41 g, 2 mmol) are put
In 50 mL reactors；
(2) oxolane that 20 mL are dried is added under nitrogen protection；
(3) it is cooled to-5 DEG C；
(4) 3.6 mL(9 mmol are added) n-BuLi hexane solution (2.5 mol/L), reacts 1 hour；
(5) 4-methoxy benzophenone (3.40 g, 16 mmol) is added in mixed solution；
(6) reaction temperature is risen to 70 DEG C, continue reaction 24 hours；
(7) ammonium chloride solution adding 10% makes reaction stop；
(8) extract (3 × 50 mL) with dichloromethane, merge organic phase, wash with saturated aqueous common salt；
(9) use anhydrous magnesium sulfate to be removed by solvent after drying, obtain tertiary alcohol intermediate product；
(10) it is placed in obtaining intermediate product in the 150 mL round-bottomed flasks with Dean-Stark hydrophone, adds 80 mL toluene；
(11) p-methyl benzenesulfonic acid (57 mg, 0.3 mmol) is added；
(12) reactant is heated at 140 DEG C, react 4 hours；
(13), after having reacted, add the sodium bicarbonate solution washing of 10%, be dried, remove solvent；
(14) use the n-hexane containing ethyl acetate 0.5% to carry out column chromatography mutually as flowing, obtain white solid, productivity 80%.
Embodiment five
Diphenyl methylene replaces the synthesis of cup [4] aromatic compound 5
(1) by 5,11,17,23-tetra-tert-25,26,27,28-tetramethoxy cup [4] aromatic hydrocarbons (1.41 g, 2 mmol) are put
In 50 mL reactors；
(2) oxolane that 20 mL are dried is added under nitrogen protection；
(3) it is cooled to-5 DEG C；
(4) 3.6 mL(9 mmol are added) n-BuLi hexane solution (2.5 mol/L), reacts 1 hour；
(5) 4,4 '-dimethyl benzophenone (3.36 g, 16 mmol) is added in mixed solution；
(6) reaction temperature is risen to 70 DEG C, continue reaction 24 hours；
(7) ammonium chloride solution adding 10% makes reaction stop；
(8) extract (3 × 50 mL) with dichloromethane, merge organic phase, wash with saturated aqueous common salt；
(9) use anhydrous magnesium sulfate to be removed by solvent after drying, obtain tertiary alcohol intermediate product；
(10) it is placed in obtaining intermediate product in the 150 mL round-bottomed flasks with Dean-Stark hydrophone, adds 80 mL toluene；
(11) p-methyl benzenesulfonic acid (57 mg, 0.3 mmol) is added；
(12) reactant is heated at 140 DEG C, react 4 hours；
(13), after having reacted, add the sodium bicarbonate solution washing of 10%, be dried, remove solvent；
(14) use the n-hexane containing ethyl acetate 0.5% to carry out column chromatography mutually as flowing, obtain white solid, productivity 85%.
Embodiment six
Diphenyl methylene replaces the synthesis of cup [4] aromatic compound 6
(1) by 5,11,17,23-tetra-tert-25,26,27,28-tetramethoxy cup [4] aromatic hydrocarbons (1.41 g, 2 mmol) are put
In 50 mL reactors；
(2) oxolane that 20 mL are dried is added under nitrogen protection；
(3) it is cooled to-5 DEG C；
(4) 3.6 mL(9 mmol are added) n-BuLi hexane solution (2.5 mol/L), reacts 1 hour；
(5) 4,4 '-dibromobenzo-phenone (5.44 g, 16 mmol) is added in mixed solution；
(6) reaction temperature is risen to 70 DEG C, continue reaction 24 hours；
(7) ammonium chloride solution adding 10% makes reaction stop；
(8) extract (3 × 50 mL) with dichloromethane, merge organic phase, wash with saturated aqueous common salt；
(9) use anhydrous magnesium sulfate to be removed by solvent after drying, obtain tertiary alcohol intermediate product；
(10) it is placed in obtaining intermediate product in the 150 mL round-bottomed flasks with Dean-Stark hydrophone, adds 80 mL toluene；
(11) p-methyl benzenesulfonic acid (57 mg, 0.3 mmol) is added；
(12) reactant is heated at 140 DEG C, react 4 hours；
(13), after having reacted, add the sodium bicarbonate solution washing of 10%, be dried, remove solvent；
(14) use the n-hexane containing ethyl acetate 0.5% to carry out column chromatography mutually as flowing, obtain white solid, productivity 72%.
Embodiment seven
Diphenyl methylene replaces the synthesis of cup [4] aromatic compound 7
(1) by 5,11,17,23-tetra-tert-25,26,27,28-tetramethoxy cup [4] aromatic hydrocarbons (1.41 g, 2 mmol) are put
In 50 mL reactors；
(2) oxolane that 20 mL are dried is added under nitrogen protection；
(3) it is cooled to-5 DEG C；
(4) 3.6 mL(9 mmol are added) n-BuLi hexane solution (2.5 mol/L), reacts 1 hour；
(5) 4,4 '-dimethoxy-benzophenone (3.88 g, 16 mmol) is added in mixed solution；
(6) reaction temperature is risen to 70 DEG C, continue reaction 24 hours；
(7) ammonium chloride solution adding 10% makes reaction stop；
(8) extract (3 × 50 mL) with dichloromethane, merge organic phase, wash with saturated aqueous common salt；
(9) use anhydrous magnesium sulfate to be removed by solvent after drying, obtain tertiary alcohol intermediate product；
(10) it is placed in obtaining intermediate product in the 150 mL round-bottomed flasks with Dean-Stark hydrophone, adds 80 mL toluene；
(11) p-methyl benzenesulfonic acid (57 mg, 0.3 mmol) is added；
(12) reactant is heated at 140 DEG C, react 4 hours；
(13), after having reacted, add the sodium bicarbonate solution washing of 10%, be dried, remove solvent；
(14) use the n-hexane containing ethyl acetate 0.5% to carry out column chromatography mutually as flowing, obtain white solid, productivity 83%.
Claims (2)
1. diphenyl methylene replaces the preparation method of cup [4] aromatic hydrocarbons, is mainly characterized by sequentially passing through following steps:
Under nitrogen protection, by 5,11,17,23-tetra-tert-25,26,27,28-tetramethoxy cup [4] aromatic hydrocarbons are dissolved in tetrahydrochysene
In furans, it is cooled to-10-0oC, joins in mixture by the hexane solution of n-BuLi, and nitrogen is protected, stirring, reaction
After 1 hour, add 4-methyldiphenyl ketone, the 5 of the most every 1 mM, 11,17,23-tetra-tert-25,26,27,28-tetramethyls
Epoxide cup [4] aromatic hydrocarbons adds 10-20 milliliter oxolane, 4.5 mMs of n-BuLis, 8-10 mM of benzophenone, adds
After, temperature being risen to 40-70 DEG C, continues reaction 12-36 hour, the ammonium chloride solution adding 10% makes reaction stop, and reaction is mixed
Compound dichloromethane extracts, the organic phase saturated aqueous common salt washing obtained, and is dried, removes solvent, obtain in the middle of tertiary alcohol
Product, is placed in this intermediate product in the flask with Dean-Stark water knockout drum, add toluene, p-methyl benzenesulfonic acid, wherein than
Example relation is that every mM of intermediate product alcohol adds 20-50 milliliter toluene, 0.1-0.2 mM of p-methyl benzenesulfonic acid, is heated to 140
DEG C, to react 4-6 hour, point water, after having reacted, add the sodium bicarbonate solution washing of 10%, be dried, remove solvent, use contains
The n-hexane of ethyl acetate 0.5-2% carries out column chromatography mutually as flowing, obtains white solid.
Diphenyl methylene the most according to claim 1 replaces the preparation method of cup [4] aromatic hydrocarbons, it is characterised in that described
Benzophenone be selected from benzophenone, 4-bromine benzophenone, 4-methyl benzophenone, 4-methoxy benzophenone, 4,4 '-dibromo
Benzophenone, 4,4 '-dimethyl benzophenone, 4, the one in 4 '-dimethoxy-benzophenone.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108314690A (en) * | 2018-03-15 | 2018-07-24 | 中国科学院苏州生物医学工程技术研究所 | The metal complex and its synthetic method of double cup [4] arene derivatives and application |
| CN110031439A (en) * | 2019-04-22 | 2019-07-19 | 宁波大学 | A method of detection bivalent cupric ion |
| CN110642684A (en) * | 2019-10-15 | 2020-01-03 | 天津师范大学 | Macrocyclic and cage-shaped molecules based on biphenyl arene and derivative compounds thereof, and synthetic method and application thereof |
-
2016
- 2016-05-16 CN CN201610315965.9A patent/CN105884585A/en active Pending
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108314690A (en) * | 2018-03-15 | 2018-07-24 | 中国科学院苏州生物医学工程技术研究所 | The metal complex and its synthetic method of double cup [4] arene derivatives and application |
| CN108314690B (en) * | 2018-03-15 | 2019-06-07 | 中国科学院苏州生物医学工程技术研究所 | The metal complex and its synthetic method of double cup [4] arene derivatives and application |
| CN110031439A (en) * | 2019-04-22 | 2019-07-19 | 宁波大学 | A method of detection bivalent cupric ion |
| CN110031439B (en) * | 2019-04-22 | 2021-06-15 | 宁波大学 | Method for detecting divalent copper ions |
| CN110642684A (en) * | 2019-10-15 | 2020-01-03 | 天津师范大学 | Macrocyclic and cage-shaped molecules based on biphenyl arene and derivative compounds thereof, and synthetic method and application thereof |
| WO2021073456A1 (en) * | 2019-10-15 | 2021-04-22 | 天津师范大学 | Macrocyclic and cage-like molecules based on biphenylarene and derivative compounds, synthesis method therefor and use thereof |
| CN110642684B (en) * | 2019-10-15 | 2022-07-26 | 天津师范大学 | Macrocyclic and cage-shaped molecules based on biphenyl arene and derivative compounds thereof, and synthetic method and application thereof |
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Application publication date: 20160824 |