CN1353103A - Functional dendritic molecular material and its preparing process - Google Patents
Functional dendritic molecular material and its preparing process Download PDFInfo
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- CN1353103A CN1353103A CN 01132324 CN01132324A CN1353103A CN 1353103 A CN1353103 A CN 1353103A CN 01132324 CN01132324 CN 01132324 CN 01132324 A CN01132324 A CN 01132324A CN 1353103 A CN1353103 A CN 1353103A
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Abstract
A functional dendritic molecular material used for organic medium, molecular semiconductor, hole transmission materials and photochromic material is prepared from pentaerythritol tetraphenylsulfonate as initial raw material through reaction on different phenols under nitrogen atmosphere, and has tetrahedral branch structure.
Description
Technical Field
The invention belongs to the technical field of organic functional materials, and particularly relates to a functional dendritic molecular material and a preparation method thereof.
Technical Field
Inspired by the shape of the macroscopic world tree, a class of multi-branched organic molecules that diverge outward in a dendron form has been extensively studied. Such multi-branched molecules are called dendrimers (dendrimers) and have a defined space, size, shape and topology. At present, research on functional dendrimers has been expanded to the fields of material science, life science and the like, and people have conducted extensive research on the biological activity, self-assembly property, liquid crystal property, magnetism, electrical property, photosensitive property and the like of many molecules. ([1]Frechet J.M., Science, 1994, 263: 1710; [2]Zeng F.W., Zimmerman S.C., Chem.Rev., 1997, 97: 1681; [3]Archut A.Vogtle F.A., Chem.Soc.Rev., 1998, 27: 233; [4]Issberner J.A., Moors R.A., Vogtle F.an., Angel.Chem.Ed.Engl., 1994, 33: 2413; [5]ChH.F.ow, Mong T.K.et al., Tetrahedron, 1998, 54: 8543.)
The functional dendrimer is designed according to the following idea: the dendritic structure is used as a framework, and the functional small molecule is used as a functional group to be grafted to the periphery of the framework. The target function of the molecule can be realized by selecting a specific functional group, for example, an organic molecular material with specific performances of good light, electricity, magnetism and the like can be obtained. The dendritic molecules after grafting and integration are larger than the original functional small molecules and have specific spatial structures, so that the thermal stability, corrosion resistance, mechanical strength and film-forming property of the molecules can be modulated and improved.
Disclosure of Invention
The invention aims to provide a functional molecular material with a dendritic structure and a preparation method thereof.
The functional molecular material with a dendritic structure provided by the invention takes a tetrahedral pentaerythritol derivative as a skeleton for constructing a dendritic molecule, and structural units of an aromatic group are connected with the skeleton through ether bonds, so that a class of pentaerythritol tetraarylether molecular compounds is obtained.
It has a tetrahedral branching structure as shown below:
ar is an aromatic group.
These molecular compounds have various functional properties and are widely used as organic dielectric materials, photochromic materials, carrier transport materials, molecular semiconductors, and the like.
Different compounds can be constructed by selecting different aromatic groups (Ar) and linking them via ether linkages and pentaerythrityl groups. Such as: (1) when the aryl group is 3, 5-dimethylphenyl, the compound (A) is obtained
The names of Chinese characters are: pentaerythrityl tetrakis (3, 5-dimethylphenyl) ether;
the english name is: pentaerythrityl tetra (3, 5-dimethoxyphenyl) ether;
IUPAC name: 1- (2, 2-bis (3, 5-dimethylphenoxy) methyl) -3- (3, 5-dimethylphenoxy) propoxy) -3, 5-dimethyllbenzene.
Molecular formula C37H44O4The structural formula is shown as the following figure:(2) when the aryl group is 4-tert-butylphenyl, the compound (B) is obtained
The names of Chinese characters are: pentaerythrityl tetrakis (4-tert-butylphenyl) ether;
the english name is: pentaerythrityl tetra (4- (tert-butyl) phenyl) ether;
IUPAC name: 1- (2, 2-bis ((4- (tert-butyl) phenoxy) methyl) -3- (4- (tert-butyl) phenoxy) proxy) -4- (tert-butyl) bezene
Molecular formula C45H60O4The structural formula is shown as the following figure:
(3) when the aromatic group is a biphenyl group, a compound (C) is obtained
The names of Chinese characters are: pentaerythrityl tetrakis (4-phenylphenyl) ether;
the english name is: pentaerythrityl tetra (4-phenylphenyl) ether;
IUPAC name: 1- (2, 2-bis ((4-phenylphenoxy) methyl) -3- (4-phenylphenoxy) propoxy) -4-phenylbenzene
Molecular formula C53H44O4The structural formula is shown as the following figure:
(4) when the aryl group is 2-naphthyl, the compound (D) is obtained
The names of Chinese characters are: pentaerythrityl tetrakis (2-naphthyl) ether;
the english name is: pentaerythrityl tetra (2-napthyl) ether;
IUPAC name: 2- (2, 2-bis (2-naphthoxymethyl) -3- (2-naphthoxy) propoxy) naphthalene
Molecular formula C45H36O4The structural formula is shown as the following figure:
(5) when the aryl group is 8-quinolyl, the compound (E) is obtained. The names of Chinese characters are: pentaerythrityl tetrakis (8-quinolinyl) ether;
the english name is: pentaerythrityl tetra (8-quinolinyl) ether;
IUPAC name: 8- (2, 2-bis (8-quinolyloxymethyl) -3- (8-quinolyloxy) propoxy) quinoline
Molecular formula C41H32N4O4The structural formula is shown as the following figure:(6) when the aromatic group is 3-dimethylaminophenyl, the compound (F) is obtained
The names of Chinese characters are: pentaerythrityl tetrakis (3-dimethylaminophenyl) ether;
the english name is: pentaerythrityl tetra (3- (dimethyllamino) phenyl) ether;
IUPAC name: (3- (2, 2-bis (3- (dimethylamino) phenoxy) methyl) -3- (3- (dimethylamino) phenoxy) phenyl) dimethyl amine
Molecular formula C37H48N4O4The structural formula is shown as the following figure:(7) when the aryl group is 4-phenylazoylphenyl, the compound (G) is obtained
The names of Chinese characters are: pentaerythrityl tetrakis (4-phenylazophenyl) ether;
the english name is: pentaerythrityl tetra (4- (phenyldiazenyl) phenyl) ether;
IUPAC name: (4- (2, 2-bis ((4- (phenyldiazenyl) phenoxy) methyl) -3- (4- (phenyldiazenyl) phenoxy) propoxy) phenyl) phenyldiazene
Molecular formula C53H44N8O4The structure is shown in the following figure:
the invention also provides a synthesis method of the dendritic molecule. These organic molecules are obtained by reacting the corresponding potassium phenolate with pentaerythritol tetraphenylsulfonate, the chemical reaction being as follows:
specific synthetic procedures
A certain amount of phenol (ArOH) was dissolved in methanol, and the solution was added dropwise to a methanol solution containing an equivalent amount of potassium hydroxide at room temperature, and the methanol may be in excess. And continuing to react for 10-30 minutes, and pumping out methanol under a reduced pressure condition to obtain a corresponding phenol potassium salt solid. Adding DMF (N, N-dimethylformamide) or TG (tetraglyme) as a solvent under anhydrous and oxygen-free conditions, and dissolving to obtain a potassium phenolate solution with the concentration of 0.5-3 mol/L. And dropwise adding a DMF (dimethyl formamide) solution of pentaerythritol tetraphenyl sulfonate (with the concentration of 0.1-0.5 mol/L) into the solution, and heating to 70-140 ℃ after dropwise adding for reaction for 10-24 hours. In the above step, the molar ratio of phenol to potassium hydroxide to pentaerythritol tetraphenyl sulfonate is 0.8-1.2 and 6-4, respectively. After the reaction is finished, the reaction liquid is cooled, poured into a large amount of ice water again, precipitates are separated out, and a crude product is obtained by filtration. The product can be recrystallized by using solvents such as ethanol, acetone and the like, and the yield is 30-90%.
In the above process, if the phenol is 3, 5-dimethylphenol, compound (A) is obtained, the formula and the formula of which are identical to those described above.
In the above process, if the phenol is 4-tert-butylphenol, compound (B) is obtained, the structural formula and the molecular formula of which are the same as those described above.
In the above process, if the phenol is a biphenol, a compound (C) is obtained, the formula and the molecular formula of which are identical to those described above.
In the above process, if the phenol is 2-naphthol, the compound (D) is obtained, the structural formula and the molecular formula of which are the same as those described above.
In the above process, if the phenol is 8-hydroxyquinoline, compound (E) is obtained, the structural formula and the molecular formula of which are the same as those described above.
In the above process, if the phenol is 3-dimethylaminophenol, a compound (F) is obtained which has a formula and a molecular formula equivalent to those described above.
In the above process, if the phenol is 4-phenylazophenol, the compound (G) is obtained, the structural formula and the molecular formula of which are the same as those described above.
The molecules of the pentaerythritol tetraarylether obtained by the invention have a dendritic structure of a tetrahedral shape, the molecules can be formed into films by vacuum thermal evaporation, and the molecular materials can be used as organic media, molecular semiconductors and the like. Wherein the compounds (A) and (B) are useful as organic media and the compounds (C), (D), (E), (F) and (G) are molecular semiconductors. The crystal structure of the compound (C) belongs to a monoclinic system, and stacking action, namely pi-pi interaction, exists between adjacent molecular terminal phenyl groups, and the interaction can be that a pi conjugated structure in a molecule extends in a molecular crystal and influences the electrical property of a molecular material.
These organic molecules also have a wide range of uses in many specific areas, such as:
the compound (F) has a high carrier transport ability and is an excellenthole transport material. When ITO glass is used as a bottom electrode, the compound (F) is used as a hole transport layer, 8-hydroxyquinoline aluminum is used as a light-emitting layer, and Mg-Ag is used as a top electrode, an organic light-emitting device with high light-emitting efficiency can be manufactured. Therefore, the organic flat display device has wide application value in the field of organic flat display devices.
The compound (G) is a polyazo dendrimer having 4 azobenzene functional units, each azobenzene unit having both cis and trans isomeric forms. Under the action of light with different wavelengths, the molecule can be subjected to reversible photochromic isomerization conversion, is a reversible photochromic material and can be used for developing a light-operated molecular switch. In addition, the molecule can also be used as a multi-photon absorption material and a multi-photon emission material, namely, each molecule can simultaneously absorb a plurality of photons and simultaneously emit a plurality of photons, and the molecule has important application in the technical field of molecular laser.
The invention is further described below by way of examples
Example 1
2 g of potassium hydroxide (82%, 30 mmol) was dissolved in 15 ml of methanol, 10 ml of a methanol solution containing 30 mmol of 3, 5-dimethylphenol was added dropwise under a nitrogen atmosphere, and after 20 minutes of reaction at room temperature, the methanol was removed under reduced pressure to obtain a potassium phenolate salt. 15 ml of TG were added, dissolved with stirring, and a DMF solution (15 ml) containing 5 mmol (3.48 g) of pentaerythritol tetraphenyl sulfonate was added dropwise. After the dripping is finished, the temperature is raised to 120 ℃ for reaction for 20 hours. After cooling, the reaction solution was poured into 200 ml of ice water, a white solid precipitated, and filtered to obtain a crude product. Then recrystallizing with 95% ethanol to obtain white crystal, i.e. compound (A).
The yield is 65%; m.p. 100-; IR (cm)-1)：3020，2936，1594，1458，1150，1065.1H-NMR(60MHz，CCl4，δ)：6.3(s，12H)，4.1(s，8H)，2.1(s，24H).
Example 2
2 g of potassium hydroxide (82%, 30 mmol) was dissolved in 15 ml of methanol, 10 ml of a methanol solution containing 30 mmol of 4-tert-butylphenol was added dropwise under a nitrogen atmosphere, and after 20 minutes of reaction at room temperature, methanol was removed under reduced pressure to obtain a potassium phenolate. 15 ml of TG were added, dissolved with stirring, and a DMF solution (15 ml) containing 5 mmol (3.48 g) of pentaerythritol tetraphenyl sulfonate was added dropwise. After the dripping is finished, the temperature is raised to 120 ℃ for reaction for 20 hours. After cooling, the reaction solution was poured into 200 ml of ice water, a white solid precipitated, and filtered to obtain a crude product. Then recrystallized by ethanol and acetone to obtain white powder, namely the compound (B).
The yield is 64%; 157 ℃ under 156. p. -; IR (cm)-1)：3050，2962，1515，1466，1244，1053.1H-NMR(60MHz，CCl4，δ)：6.5-7.1(m，16H)，4.1(s，8H)，1.1(s，36H).
Example 3
2 g of potassium hydroxide (82%, 30 mmol) was dissolved in 15 ml of methanol, 10 ml of a methanol solution containing 30 mmol of 4-phenylphenol was added dropwise under a nitrogen atmosphere, and after 20 minutes of reaction at room temperature, the methanol was removed under reduced pressure to obtain a potassium phenolate. 15 ml of TG were added, dissolved with stirring, and a DMF solution (15 ml) containing 5 mmol (3.48 g) of pentaerythritol tetraphenyl sulfonate was added dropwise. After the dripping is finished, the temperature is raised to 120 ℃ for reaction for 20 hours. After cooling, the reaction solution was poured into 200 ml of ice water, and a solid precipitated and filtered to obtain a crude product. And then recrystallized from acetone to obtain colorless granular crystals, i.e., compound (C).
The yield is 71%; m.p. ═ 140 ℃; IR (cm)-1)：3030，2933，1610，1485，1241，1024.1H-NMR(60MHz，CCl4，δ)：6.8-7.5(m，36H)，4.3(s，8H).
Example 4
2 g of potassium hydroxide (82%, 30 mmol) was dissolved in 15 ml of methanol, 10 ml of a methanol solution containing 30 mmol of 2-naphthol was added dropwise under a nitrogen atmosphere, and after 20 minutes at room temperature, the methanol was removed under reduced pressure to obtain a potassium phenolate. 15 ml of TG were added, dissolved with stirring, and a DMF solution (15 ml) containing 5 mmol (3.48 g) of pentaerythritol tetraphenyl sulfonate was added dropwise. After the dripping is finished, the temperature is raised to 120 ℃ for reaction for 20 hours. After cooling, the reaction solution was poured into 200 ml of ice water, and a solid precipitated and filtered to obtain a crude product. Then recrystallized by 95% ethanol to obtain a yellowish white powder, i.e., compound (D).
The yield is 70%; 106-; IR (cm)-1)：3059，2920，1627，1457，1213，1020.1H-NMR(60MHz，CCl4，δ)：7.0-7.6(m，28H)，4.5(s，8H).
Example 5
2 g of potassium hydroxide (82%, 30 mmol) was dissolved in 15 ml of methanol, 10 ml of a methanol solution containing 30 mmol of 8-hydroxyquinoline was added dropwise under a nitrogen atmosphere, and the mixture was reacted at room temperature for 20minutes, followed by removal of methanol under reduced pressure to obtain a potassium phenolate salt. 15 ml of TG were added, dissolved with stirring, and a DMF solution (15 ml) containing 5 mmol (3.48 g) of pentaerythritol tetraphenyl sulfonate was added dropwise. After the dripping is finished, the temperature is raised to 120 ℃ for reaction for 20 hours. After cooling, the reaction solution was poured into 200 ml of ice water, and a solid precipitated and filtered to obtain a crude product. Then recrystallizing with 95% ethanol to obtain purple black powder, i.e. compound (E).
The yield is 38%; m.p. 148-; IR (cm)-1)：3047，2935，1571，1460，1260，1090.1H-NMR(60MHz，CDCl3，δ)：8.5-8.9(m，4H)，7.7-8.0(m，4H)，6.9-7.5(m，12H)，6.0-6.6(m，4H)，4.6(s，8H).
Example 6
2 g of potassium hydroxide (82%, 30 mmol) was dissolved in 15 ml of methanol, 10 ml of a methanol solution containing 30 mmol of 3-dimethylaminophenol was added dropwise under a nitrogen atmosphere, and after 20 minutes of reaction at room temperature, the methanol was removed under reduced pressure to obtain a potassium phenolate. 15 ml of TG were added, dissolved with stirring, and a DMF solution (15 ml) containing 5 mmol (3.48 g) of pentaerythritol tetraphenyl sulfonate was added dropwise. After the dripping is finished, the temperature is raised to 120 ℃ for reaction for 20 hours. After cooling, the reaction solution was poured into 200 ml of ice water, and a solid precipitated and filtered to obtain a crude product. Then recrystallized with 95% ethanol to obtain purple powder, i.e., compound (F).
The yield is 40%; m.p. 170-; IR (cm)-1)：3010，2935，1615，1445，1153，1061.1H-NMR(60MHz，CDCl3，δ)：6.7-7.2(m，4H)，6.0-6.3(m，12H)，4.2(s，8H)，2.7(s，24H)。
Example 7
2 g of potassium hydroxide (82%, 30 mmol) was dissolved in 15 ml of methanol, 10 ml of a methanol solution containing 30 mmol of 4-phenylazophenol was added dropwise under a nitrogen atmosphere, reacted at room temperature for 20 minutes, and the methanol was removed under reduced pressure to obtain a potassium phenolate. 15 ml of TG were added, dissolved with stirring, and a DMF solution (15 ml) containing 5 mmol (3.48 g) of pentaerythritol tetraphenyl sulfonate was added dropwise. After the dripping is finished, the temperature is raised to 120 ℃ for reaction for 20 hours. After cooling, the reaction solution was poured into 200 ml of ice water, and a solid precipitated and filtered to obtain a crude product. And then recrystallizing with acetone to obtain orange red crystal, namely the compound (G).
The yield is 71%; 197-; IR (cm)-1)：3059，2933，1599，1581，1499，1239，1140.1H-NMR(500MHz，CDCl3，δ)：7.93(d，8H)，7.87(d，8H)，7.49(t，8H)，7.44(t，4H)，7.09(d，8H)，4.53(s，8H).13C-NMR(125MHz，CDCl3，δ)：161.1，152.7，147.4，130.5，129.0，124.8，122.6，114.9，44.9。
Claims (16)
1. A functional dendritic molecular material is characterized in that the functional dendritic molecular material is formed by connecting a tetrahedral pentaerythritol derivative serving as a framework with various aromatic groups through ether bonds, and the technical structure is as follows:
wherein Ar is an aromatic group.
2. The functional dendritic molecular material of claim 1 wherein the aromatic group is a 3, 5-dimethylphenyl group having the chemical formula:
molecular formula C37H44O4。
3. The functional dendritic molecular material of claim 1 wherein the aromatic group is 4-t-butylphenyl having the chemical formula:molecular formula C45H60O4。
4. The functional dendritic molecular material of claim 1 wherein the aromatic group is a biphenyl group having the chemical formula:
molecular formula C53H44O4。
5. The functional dendritic molecular material of claim 1 wherein the aromatic group is a 2-naphthyl group having the chemical formula:
molecular formula C45H36O4。
6. The functional dendrimer material of claim 1, wherein the aryl group is an 8-quinolinyl group having the chemical formula:
molecular formula C41H32N4O4。
7. The functional dendritic molecular material of claim 1 wherein the aromatic group is 3-dimethylaminophenyl group having the chemical formula:molecular formula C37H48N4O4。
8. The functional dendritic molecular materialof claim 1 wherein the aromatic group is 4-phenylazophenyl and has the chemical formula:
molecular formula C53H44N8O4。
9. A preparation method of the functional dendritic molecular material as claimed in claim 1, wherein pentaerythritol tetraphenylsulfonate is used as a starting material, and the functional dendritic molecular material is prepared by reacting with phenol in a nitrogen atmosphere, and is characterized in that the method comprises the specific steps of dropwise adding methanol solution of phenol into potassium hydroxide methanol solution with equivalent weight, reacting for 10-30 minutes, and removing methanol under reduced pressure to obtain phenol potassium salt solid; adding DMF or TG as a solvent under anhydrous and anaerobic conditions, then dropwise adding a DMF solution of pentaerythritol tetraphenyl sulfonate, and reacting for 10-24 hours at 70-140 ℃; in the above step, the molar ratio of phenol to potassium hydroxide to pentaerythritol tetraphenyl sulfonate is 0.8-1.2 and 6-4 respectively; after the reaction is finished, cooling, pouring into a large amount of ice water again, separating out precipitate, and filtering to obtain a crude product.
10. The process according to claim 9, wherein the phenol used is 3, 5-dimethylphenol, giving compound (A).
11. The process according to claim 9, wherein the phenol used is 4-tert-butylphenol, giving compound (B).
12. The process according to claim 9, wherein the phenol used is biphenol to give compound (C).
13. The process according toclaim 9, wherein the phenol used is 2-naphthol to obtain compound (D).
14. The process according to claim 9, wherein the phenol used is 8-hydroxyquinoline to give compound (E).
15. The process according to claim 9, wherein the phenol used is m-xylenol to give compound (F).
16. The process according to claim 9, wherein the phenol used is 4-phenylazoylphenol to obtain the compound (G).
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104591979A (en) * | 2013-11-01 | 2015-05-06 | 中国石油化工股份有限公司 | Compound, catalyst solid component containing compound, and catalyst |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN104591979A (en) * | 2013-11-01 | 2015-05-06 | 中国石油化工股份有限公司 | Compound, catalyst solid component containing compound, and catalyst |
| CN104591979B (en) * | 2013-11-01 | 2016-09-21 | 中国石油化工股份有限公司 | A kind of compound, catalyst solid constituent containing described compound and catalyst |
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