CN109336776A - It is a kind of to replace conjugated compound and its application by the big steric hindrance alkoxy of end group of triaryl amine - Google Patents
It is a kind of to replace conjugated compound and its application by the big steric hindrance alkoxy of end group of triaryl amine Download PDFInfo
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- CN109336776A CN109336776A CN201811429343.4A CN201811429343A CN109336776A CN 109336776 A CN109336776 A CN 109336776A CN 201811429343 A CN201811429343 A CN 201811429343A CN 109336776 A CN109336776 A CN 109336776A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
- C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
- C07C217/84—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
- C07C217/86—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical containing six-membered aromatic rings
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
Abstract
It is a kind of to replace conjugated compound by the big steric hindrance alkoxy of end group of triaryl amine, it is related to organic synthesis field, structural formula I is as follows:Wherein, Ar is phenyl, naphthalene or anthryl, R1For H, CH3Or OCH3, R2For big steric hindrance alkoxy chain.The present invention is selected using the preferably organic triaryl amine of stability as redox active end group, using the conjugated ligand for being tied with dendroid alkoxy grp as bridge chain, has synthesized the compound of big steric hindrance alkoxy chain attachment.By electrochemical test it is found that having extremely strong electron interaction between the end group of the triaryl amine conjugated compound in the present invention, charge transport ability is preferable, particularly suitable to be applied in insulating molecule conducting wire.
Description
Technical field
The present invention relates to organic synthesis fields, are related specifically to a kind of using triaryl amine as the substitution of the big steric hindrance alkoxy of end group
Conjugated compound and its application.
Background technique
Molecular wire is molecular electronic device connection bridge and the essential elements for realizing electronic device micromation, numerous studies
The result shows that the charge transport ability of molecular wire exponentially decays with the increase of molecular length.Triaryl amine has excellent
Electro-chemical activity and stability, scientists have synthesized many new compounds using it as end group in recent years, and expect this
A little compounds have good charge transport ability.But what things turn out contrary to one's wishes is, in practice it has proved that it is most with triaryl amine be end
The mutual ability of the electronics of the compound of base is weaker, and the performance of manufactured insulating molecule conducting wire is also difficult to reach relevant application mark
It is quasi-.
Summary of the invention
The purpose of the present invention is to provide between a kind of end group with extremely strong electron interaction using triaryl amine as end group
Big steric hindrance alkoxy replace conjugated compound.
In order to solve the above-mentioned technical problem, the present invention adopts the following technical scheme: it is a kind of using triaryl amine as the big position of end group
It hinders alkoxy and replaces conjugated compound, structural formula I is as follows:
Wherein, Ar is phenyl, naphthalene or anthryl, R1For H, CH3Or OCH3,
R2For
A kind of to replace conjugated compound by the big steric hindrance alkoxy of end group of triaryl amine, structural formula I-1 is as follows:
Corresponding preparation method the following steps are included: be added into container 4- borate -4', 4'- dimethoxy triphenylamine,
Then 2,5- bis- (4- tert-butylbenzyloxy)-Isosorbide-5-Nitrae-diiodo-benzenes, tetrakis triphenylphosphine palladium are added under nitrogen protection and have deaerated
The solution of potassium carbonate of toluene, ethyl alcohol and 2mol/L is cooled to room temperature after flowing back for 24 hours at 110 DEG C to system, through diatomite
It filters to get filtrate, is spin-dried for, after progress column chromatography for separation to obtain the final product.
A kind of to replace conjugated compound by the big steric hindrance alkoxy of end group of triaryl amine, structural formula I-2 is as follows:
Corresponding preparation method the following steps are included: into container addition 4- borate -4', 4'- dimethoxy triphenylamine,
Isosorbide-5-Nitrae-diiodo-benzene, the tetrakis triphenylphosphine palladium of dendroid radical protection, pumping fill N2Three times, it is then added and has taken off under nitrogen protection
The solution of potassium carbonate of the toluene of gas, ethyl alcohol and 2mol/L is cooled to room temperature after flowing back for 24 hours at 110 DEG C to system, through silicon
Diatomaceous earth filters to get filtrate, and is spin-dried for, after progress column chromatography for separation to obtain the final product.
In the preparation process that the big steric hindrance alkoxy of both the above replaces conjugated compound, the elution used of when column chromatography for separation
Agent is made of the methylene chloride that volume ratio is 1:1 and petroleum ether, and the mesh number of used silica gel is 200-300 mesh.
A kind of to replace conjugated compound by the big steric hindrance alkoxy of end group of triaryl amine, structural formula II is as follows:
Wherein, Ar is phenyl, naphthalene or anthryl, R1For H, CH3Or OCH3,
R2For
A kind of to replace conjugated compound by the big steric hindrance alkoxy of end group of triaryl amine, structural formula II -1 is as follows:
Corresponding preparation method is the following steps are included: 4- acetenyl triphenylamine and (the tertiary fourth of 4- of 2,5- bis- are added into container
Base benzyloxy)-Isosorbide-5-Nitrae-diiodo-benzene, tetrakis triphenylphosphine palladium, cuprous iodide, the tetrahydro to have deaerated is then added under nitrogen protection
Furans and triethylamine flow back for 24 hours at 80 DEG C, after system is cooled to room temperature, filter to get filtrate, be spin-dried for through diatomite, into
After row column chromatography for separation to obtain the final product.
A kind of to replace conjugated compound by the big steric hindrance alkoxy of end group of triaryl amine, structural formula II -2 is as follows:
Corresponding preparation method is the following steps are included: 4- acetenyl triphenylamine is added into container, dendroid group replaces
Isosorbide-5-Nitrae-diiodo-benzene, tetrakis triphenylphosphine palladium, cuprous iodide, the tetrahydrofuran to have deaerated and three are then added under nitrogen protection
Ethamine flows back for 24 hours at 80 DEG C, after system is cooled to room temperature, filters to get filtrate, be spin-dried for through diatomite, carries out column chromatography
After separation to obtain the final product.
In the preparation process that the big steric hindrance alkoxy of both the above replaces conjugated compound, the elution used of when column chromatography for separation
Agent is made of the methylene chloride that volume ratio is 1:2 and petroleum ether, and the mesh number of used silica gel is 200-300 mesh.
Triaryl amine conjugated compound provided by the invention can be applied to production molecular wire material.
Compared to the prior art, the invention has the following advantages: present invention selection is with stability preferable organic three
Arylamine is redox active end group, and the conjugated ligand for being tied with dendroid alkoxy grp is bridge chain, has synthesized big steric hindrance alkoxy chain
The compound of attachment.By electrochemical test it is found that having between the end group of the triaryl amine conjugated compound in the present invention extremely strong
Electron interaction, charge transport ability is preferable, it is particularly suitable be applied to insulating molecule conducting wire in.
Specific embodiment
Embodiment is given below so that the present invention to be specifically described, it is necessary to which indicated herein is following embodiment
It is used to further illustrate the present invention, should not be understood as limiting the scope of the invention, the ordinary skill in the field
Personnel still fall within protection scope of the present invention to some nonessential improvement of the invention made or adjustment according to this embodiment.
Embodiment 1
A kind of to replace conjugated compound by the big steric hindrance alkoxy of end group of triaryl amine, the compound is by being tied with dendroid
The phenyl bridging of alkoxy grp, preparation method are as follows:
Into 50mL double-neck flask be added 0.46mmol 4- borate -4', 4'- dimethoxy triphenylamine (200mg),
0.21mmol 2,5- bis- (4- tert-butylbenzyloxy) -1,4- diiodo-benzene (137mg), 0.01mmol tetrakis triphenylphosphine palladium
(12mg), system pumping fill N2Three times, the 10mL toluene, 2mL ethyl alcohol and 2mL 2mol/ to have deaerated is then added under nitrogen protection
The solution of potassium carbonate of L, after flowing back for 24 hours at 110 DEG C, system is cooled to room temperature, and is filtered to get filtrate through diatomite, is spin-dried for, column
Chromatography obtains the yellow solid that 112mg structural formula is I-1, yield: 53%.
During column chromatography for separation, used silica gel is 200-300 mesh, and it is the dichloro of 1:1 that eluant, eluent used, which selects volume ratio,
Methane and petroleum ether.
Structural formula I-1 is as follows:
Elemental analysis (C68H68N2O6): theoretical value: C, 80.92；H, 6.79.Measured value: C, 80.81；H, 6.85.
Structured data:1H NMR(500MHz,CDCl3):δ1.32(s,18H,CH3),3.80(s,12H,-OCH3),4.97
(s, 4H), 6.85 (d, J (HH)=5.0Hz, 6H), 6.98 (d, J (HH)=5.0Hz, 4H), 7.06 (s, 2H), 7.11 (d, J
(HH)=10.0Hz, 7H), 7.27 (s, 2H), 7.34-7.38 (m, 7H), 7.43 (d, J (HH)=10.0Hz, 4H), 7.69 (s,
2H).
13C NMR(125MHz,CDCl3):δ31.36,34.53,55.48,71.70,114.64,117.09,120.14,
125.24,126.50,127.05,127.64,130.08,130.22,130.69,134.49,135.21,141.06,147.61,
150.41,150.51,155.76。
Embodiment 2
A kind of to replace conjugated compound by the big steric hindrance alkoxy of end group of triaryl amine, the compound is by being tied with dendroid
The phenyl bridging of alkoxy grp, preparation method are as follows:
1.71mmol 4- borate -4', 4'- dimethoxy triphenylamine (737mg), tree are added into 50mL double-neck flask
0.81mmol Isosorbide-5-Nitrae-diiodo-benzene (965mg) of dendrimeric group protection, 0.08mmol tetrakis triphenylphosphine palladium (94mg), system are taken out
Fill N2Three times, the solution of potassium carbonate of toluene, 2mL ethyl alcohol and 2mol/L that 10mL has deaerated then are added under nitrogen protection, then
After flowing back for 24 hours at 110 DEG C, system is cooled to room temperature, and filtering (through diatomite) obtains filtrate, is spin-dried for, column chromatography for separation obtains
200mg structural formula is the white solid of I-2, yield: 64%.
During column chromatography for separation, used silica gel is 200-300 mesh, and it is the dichloro of 1:1 that eluant, eluent used, which selects volume ratio,
Methane and petroleum ether.
Structural formula I-2 is as follows:
Elemental analysis (C104H108N2O10): theoretical value: C, 80.80；H, 7.04.Measured value: C, 80.91；H, 6.97.
Structured data:1H NMR(500MHz,CDCl3):δ1.31(s,36H,-CH3),3.76(s,12H,-OCH3),4.92
(s,8H,-CH2),4.99(s,4H,-CH2), 6.52 (s, 2H), 6.63 (s, 4H), 6.78 (d, J (HH)=10.0Hz, 4H),
6.98 (d, J (HH)=5.0Hz, 4H), 7.04 (t, J (HH)=10.0Hz, 10H), 7.30 (d, J (HH)=10.0Hz, 8H),
7.37 (d, J (HH)=10.0Hz, 8H), 7.47 (d, J (HH)=10.0Hz, 4H).
13C NMR(125MHz,CDCl3):δ31.31(CH3),31.57,34.54,55.40,69.92,101.41,
105.49,114.60,116.57,119.76,125.50,126.61,127.61,129.99,130.07,130.36,133.36,
139.91,140.80,147.68,150.10,150.97,155.75,160.06。
Embodiment 3
A kind of to replace conjugated compound by the big steric hindrance alkoxy of end group of triaryl amine, the compound is by being tied with dendroid
The phenylacetylene base bridging of alkoxy grp, preparation method are as follows:
1.71mmol 4- acetenyl triphenylamine (460mg), (the 4- tert-butyl benzyl of 2,5- bis- are added in 50mL double-neck flask
Oxygroup)-Isosorbide-5-Nitrae-diiodo-benzene (530mg, 0.81mmol), 0.17mmol tetrakis triphenylphosphine palladium (94mg), 0.17mmol iodate Asia
Copper (15mg), system pumping fill N2Three times, the 20mL tetrahydrofuran and 10mL triethylamine to have deaerated is then added under nitrogen protection,
After flowing back for 24 hours at 80 DEG C, system is cooled to room temperature, and is filtered to get filtrate through diatomite, is spin-dried for, and column chromatography for separation obtains
505mg structural formula is the yellow solid of II-1, yield: 67%.
During column chromatography for separation, used silica gel is 200-300 mesh, and it is the dichloro of 1:2 that eluant, eluent used, which selects volume ratio,
Methane and petroleum ether.
Formula II -1 is as follows:
Elemental analysis (C68H60N2O2): theoretical value: C, 87.14；H, 6.45.Measured value: C, 87.06；H, 6.59.
Structured data:1H NMR(500MHz,CDCl3):δ1.30(s,18H,-CH3),5.12(s,4H,-OCH2),6.99
(d, J (HH)=5.0Hz, 4H), 7.06 (t, J (HH)=10.0Hz, 6H), 7.12 (d, J (HH)=5.0Hz, 8H), 7.28 (t, J
(HH)=10.0Hz, 8H), 7.34 (d, J (HH)=10.0Hz, 4H), 7.39 (d, J (HH)=10.0Hz, 4H), 7.45 (d, J
(HH)=10.0Hz, 4H)
13C NMR(125MHz,CDCl3):δ31.36(CH3),34.55,71.53,85.34,95.64,123.55,
125.00,125.34,127.01,129.38,147.19,147.93,150.76,153.68。
Embodiment 4
A kind of to replace conjugated compound by the big steric hindrance alkoxy of end group of triaryl amine, the compound is by being tied with dendroid
The phenylacetylene base bridging of alkoxy grp, preparation method are as follows:
1.71mmol 4- acetenyl triphenylamine (460mg), 0.81mmol dendroid group are added in 50mL double-neck flask
Substituted Isosorbide-5-Nitrae-diiodo-benzene (965mg), 0.17mmol tetrakis triphenylphosphine palladium (94mg), cuprous iodide (15mg, 0.17mmol),
System pumping fills N2Three times, the 20mL tetrahydrofuran and 10mL triethylamine to have deaerated, reaction mixing are then added under nitrogen protection
After object flows back for 24 hours at 80 DEG C, system is cooled to room temperature, and is filtered to get filtrate through diatomite, is spin-dried for, and column chromatography for separation obtains
810mg structural formula is the orange solids of II-2, yield: 68%.
During column chromatography for separation, used silica gel is 200-300 mesh, and it is the dichloro of 1:2 that eluant, eluent used, which selects volume ratio,
Methane and petroleum ether.
It is the methylene chloride and petroleum ether of 1:1 that eluant, eluent used, which selects volume ratio,.
Formula II -2 is as follows:
Elemental analysis (C104H100N2O6): theoretical value: C, 84.75；H, 6.84.Measured value: C, 84.90；H, 6.75.
Structured data:1H NMR(500MHz,CDCl3):δ1.30(s,36H,-CH3),4.95(s,8H,-CH2),5.12
(s,4H,-CH2), 6.56 (t, J (HH)=5.0Hz, 2H), 6.81 (s, 4H), 6.95 (d, J (HH)=10.0Hz, 4H), 7.06
(dd, J (HH)=10.0Hz, 14H), 7.25 (t, J (HH)=10.0Hz, 8H), 7.29 (d, J (HH)=5.0Hz, 8H), 7.36
(d, J (HH)=10.0Hz, 8H), 7.39 (d, J (HH)=5.0Hz, 4H)
13C NMR(125MHz,CDCl3):δ31.34(CH3),34.56,70.02,71.45,85.18,95.75,
101.69,105.83,114.75,116.12,117.90,122.20,123.55,125.01,125.48,127.55,129.38,
132.62,133.82,139.53,147.16,147.99,150.98,153.51,160.27。
Electrochemical measurement test
Using equipment: electrochemical workstation CHI 660D (CH Instruments Company, USA).
Using glass-carbon electrode as working electrode, platinum electrode is made to electrode, Ag+| Ag electrode is reference electrode.With 0.001mol
L-1n-Bu4NPF6CH2Cl2Solution is electrolyte, is tested the concentration 0.001mol L of substrate-1。
Cyclic voltammetric is usually with sweep speed for 100mV s-1It measures, square wave volt-ampere measures under the conditions of f=10Hz.
Data processing: picture is processed data by OriginPro 8.0.
Conjugation organism is replaced to carry out cyclic voltammetric and square wave big steric hindrance dendroid alkoxy by electrochemical method
Volt-ampere test, has obtained corresponding electrochemical parameter, concrete outcome is as shown in table 1.
Big steric hindrance alkoxy replaces the electrochemical test data of conjugated compound in 1 embodiment 1-4 of table
| Compound | E1/2(1)(V) | E1/2(2)(V) | ΔE(mV)b | Kc c |
| I-1 | 0.74 | 0.95 | 210 | 3.50×103 |
| I-2 | 0.73 | 0.97 | 240 | 1.12×104 |
| II-1 | 0.96 | 1.03 | 70 | 15 |
| II-2 | 0.94 | 1.04 | 100 | 48 |
As shown in Table 1, (I-1, I-2 are the first kind, II-1, II-2 second to two classes series compound prepared by the present invention
Class) continuous one electron redox process twice is presented, the potential difference Δ E value redox twice tested
It can reach 70-240mV.The potential difference of first kind compound has reached 200mV or more, and the second class triaryl amine of class containing alkynyl
Object is closed since in contrast farther out, the Δ E value tested is relatively small compared with first kind compound for distance between end group.This
The technical staff in field will be apparent to the skilled artisan that more than two class series compounds be significantly increased between end group compared with the existing technology
The electronics effect of intercoupling, in insulating molecule conducting wire field, there are huge application prospects.
Claims (9)
1. a kind of replace conjugated compound by the big steric hindrance alkoxy of end group of triaryl amine, which is characterized in that the following institute of structural formula I
Show:
Wherein, Ar is phenyl, naphthalene or anthryl, R1For H, CH3Or OCH3,
R2For
2. big steric hindrance alkoxy according to claim 1 replaces conjugated compound, which is characterized in that when Ar is phenyl, R1For
OCH3, R2ForWhen, the big steric hindrance alkoxy replaces the structural formula I-1 of conjugated compound as follows:
Corresponding preparation method is the following steps are included: 4- borate -4', 4'- dimethoxy triphenylamine, 2,5- are added into container
Two (4- tert-butylbenzyloxy)-Isosorbide-5-Nitrae-diiodo-benzenes, tetrakis triphenylphosphine palladium, are then added the first to have deaerated under nitrogen protection
The solution of potassium carbonate of benzene, ethyl alcohol and 2mol/L is cooled to room temperature after flowing back for 24 hours at 110 DEG C to system, through diatomite mistake
It filters to obtain filtrate, is spin-dried for, after progress column chromatography for separation to obtain the final product.
3. big steric hindrance alkoxy according to claim 1 replaces conjugated compound, which is characterized in that when Ar is phenyl, R1For
OCH3, R2ForWhen, the big steric hindrance alkoxy replaces the structural formula I-2 of conjugated compound such as
Shown in lower:
Corresponding preparation method is the following steps are included: 4- borate -4', 4'- dimethoxy triphenylamine, branch are added into container
Isosorbide-5-Nitrae-diiodo-benzene, the tetrakis triphenylphosphine palladium of shape radical protection, pumping fill N2Three times, it is then added and to have deaerated under nitrogen protection
The solution of potassium carbonate of toluene, ethyl alcohol and 2mol/L is cooled to room temperature after flowing back for 24 hours at 110 DEG C to system, through diatomite
It filters to get filtrate, is spin-dried for, after progress column chromatography for separation to obtain the final product.
4. big steric hindrance alkoxy according to claim 2 or 3 replaces conjugated compound, which is characterized in that column chromatography for separation
Shi Suoyong eluant, eluent is made of the methylene chloride that volume ratio is 1:1 and petroleum ether, and the mesh number of used silica gel is 200-300 mesh.
5. a kind of replace conjugated compound by the big steric hindrance alkoxy of end group of triaryl amine, which is characterized in that structural formula II is as follows
It is shown:
R2For
6. big steric hindrance alkoxy according to claim 5 replaces conjugated compound, which is characterized in that when Ar is phenyl, R1For
H, R2ForWhen, the big steric hindrance alkoxy replaces the structural formula II -1 of conjugated compound as follows:
Corresponding preparation method is the following steps are included: 4- acetenyl triphenylamine and (the 4- tert-butyl benzyl of 2,5- bis- are added into container
Oxygroup)-Isosorbide-5-Nitrae-diiodo-benzene, tetrakis triphenylphosphine palladium, cuprous iodide, the tetrahydrofuran to have deaerated is then added under nitrogen protection
And triethylamine, it flows back at 80 DEG C for 24 hours, after system is cooled to room temperature, filters to get filtrate, be spin-dried for through diatomite, carry out column
After chromatography to obtain the final product.
7. big steric hindrance alkoxy according to claim 5 replaces conjugated compound, which is characterized in that when Ar is phenyl, R1For
H, R2ForWhen, the big steric hindrance alkoxy replaces the structural formula II -2 of conjugated compound as follows
It is shown:
4- acetenyl triphenylamine is added into container, 1,4- diiodo-benzene, the tetrakis triphenylphosphine palladium, iodate that dendroid group replaces
It is cuprous, the tetrahydrofuran and triethylamine to have deaerated is then added under nitrogen protection, flows back at 80 DEG C for 24 hours, it is cold to system
But it to after room temperature, filters to get filtrate, is spin-dried for through diatomite, carry out after column chromatography for separation to obtain the final product.
8. big steric hindrance alkoxy according to claim 6 or 7 replaces conjugated compound, which is characterized in that column chromatography for separation
Shi Suoyong eluant, eluent is made of the methylene chloride that volume ratio is 1:2 and petroleum ether, and the mesh number of used silica gel is 200-300 mesh.
9. the described in any item big steric hindrance alkoxies of claim 1-8 replace conjugated compound in insulating molecule conductor material
Using.
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