CN109336776B - Large steric hindrance alkoxy substituted conjugated compound with triarylamine as end group and application thereof - Google Patents
Large steric hindrance alkoxy substituted conjugated compound with triarylamine as end group and application thereof Download PDFInfo
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- CN109336776B CN109336776B CN201811429343.4A CN201811429343A CN109336776B CN 109336776 B CN109336776 B CN 109336776B CN 201811429343 A CN201811429343 A CN 201811429343A CN 109336776 B CN109336776 B CN 109336776B
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- 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
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- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
Abstract
A large steric hindrance alkoxy substituted conjugated compound with triarylamine as a terminal group relates to the field of organic synthesis, and the structural formula I is as follows:
wherein Ar is phenyl, naphthyl or anthryl, R1Is H, CH3Or OCH3，R2Are bulky alkoxy chains. The invention selects organic triarylamine with better stability as a redox active end group, and takes a conjugated ligand wrapped with dendritic alkoxy groups as a bridge chain to synthesize the compound attached with the alkoxy chain with large steric hindrance. Electrochemical tests show that the terminal groups of the triarylamine conjugated compound have extremely strong electronic interaction and good charge transmission capability, and the triarylamine conjugated compound is particularly suitable for being applied to insulating molecular leads.
Description
Technical Field
The invention relates to the field of organic synthesis, in particular to a conjugated compound substituted by large steric hindrance alkoxy with triarylamine as a terminal group and application thereof.
Background
The molecular wire is a key unit for connecting a molecular electronic device with a bridge and realizing the miniaturization of the electronic device, and a large number of research results show that the charge transmission capacity of the molecular wire exponentially attenuates along with the increase of the length of a molecule. Triarylamines have excellent electrochemical activity and stability, and in recent years, many new compounds have been synthesized by scientists using triarylamines as terminal groups, and these compounds are expected to have good charge transport capability. However, contrary to the above, practice has proved that most of the triarylamine-terminated compounds have weak electron interaction capability, and the performance of the insulated molecular wire made therefrom is difficult to meet the relevant application standards.
Disclosure of Invention
The invention aims to provide a conjugated compound substituted by large steric hindrance alkoxy with terminal groups of triarylamine, which has extremely strong electronic interaction between the terminal groups.
In order to solve the technical problems, the invention adopts the following technical scheme: a conjugated compound substituted by large steric hindrance alkoxy with triarylamine as a terminal group has a structural formula I shown as follows:
wherein Ar is phenyl, naphthyl or anthryl, R1Is H, CH3Or OCH3，
R2Is composed of
A conjugated compound substituted by large steric hindrance alkoxy with triarylamine as a terminal group has a structural formula I-1 shown as follows:
the corresponding preparation method comprises the following steps: adding 4-borate-4 ',4' -dimethoxy triphenylamine, 2, 5-bis (4-tert-butyl benzyloxy) -1, 4-diiodobenzene and tetrakis (triphenylphosphine) palladium into a container, then adding degassed toluene, ethanol and 2mol/L potassium carbonate solution under the protection of nitrogen, refluxing at 110 ℃ for 24h, cooling the system to room temperature, filtering with diatomite to obtain filtrate, spin-drying, and performing column chromatography separation to obtain the product.
A conjugated compound substituted by large steric hindrance alkoxy with triarylamine as a terminal group has a structural formula I-2 shown as follows:
the corresponding preparation method comprises the following steps: toAdding 4-borate-4 ',4' -dimethoxy triphenylamine, dendritic group protected 1, 4-diiodobenzene and tetrakis (triphenylphosphine) palladium into a container, and pumping and filling N2And thirdly, adding degassed toluene, ethanol and 2mol/L potassium carbonate solution under the protection of nitrogen, refluxing at 110 ℃ for 24 hours, cooling the system to room temperature, filtering with diatomite to obtain filtrate, spin-drying, and performing column chromatography separation to obtain the final product.
In the preparation process of the two compounds, the eluent used in column chromatography separation consists of dichloromethane and petroleum ether with the volume ratio of 1:1, and the mesh number of the silica gel is 200-300 meshes.
A conjugated compound substituted by large steric hindrance alkoxy with triarylamine as a terminal group has a structural formula II shown as follows:
wherein Ar is phenyl, naphthyl or anthryl, R1Is H, CH3Or OCH3，
R2Is composed of
A conjugated compound substituted by large steric hindrance alkoxy with triarylamine as a terminal group has a structural formula II-1 shown as follows:
the corresponding preparation method comprises the following steps: adding 4-ethynyltriphenylamine, 2, 5-di (4-tert-butylbenzyloxy) -1, 4-diiodobenzene, tetrakis (triphenylphosphine) palladium and cuprous iodide into a container, then adding degassed tetrahydrofuran and triethylamine under the protection of nitrogen, refluxing for 24h at 80 ℃, cooling the system to room temperature, filtering with diatomite to obtain filtrate, spin-drying, and performing column chromatography separation to obtain the product.
A conjugated compound substituted by large steric hindrance alkoxy with triarylamine as a terminal group has a structural formula II-2 shown as follows:
the corresponding preparation method comprises the following steps: adding 4-ethynyltriphenylamine, dendritic group-substituted 1, 4-diiodobenzene, tetrakis (triphenylphosphine) palladium and cuprous iodide into a container, then adding degassed tetrahydrofuran and triethylamine under the protection of nitrogen, refluxing for 24h at 80 ℃, cooling the system to room temperature, filtering with diatomite to obtain filtrate, spin-drying, and performing column chromatography separation to obtain the product.
In the preparation process of the two compounds, the eluent used in column chromatography separation consists of dichloromethane and petroleum ether with the volume ratio of 1:2, and the mesh number of the silica gel is 200-300 meshes.
The triarylamine conjugated compound provided by the invention can be applied to the preparation of molecular wire materials.
Compared with the prior art, the invention has the following beneficial effects: the invention selects organic triarylamine with better stability as the oxidation-reduction active end group, and the conjugated ligand wrapped with dendritic alkoxy group as the bridge chain, so as to synthesize the compound attached by the alkoxy chain with large steric hindrance. Electrochemical tests show that the terminal groups of the triarylamine conjugated compound have extremely strong electronic interaction and good charge transmission capability, and the triarylamine conjugated compound is particularly suitable for being applied to insulating molecular leads.
Detailed Description
The following examples are given to illustrate the present invention and it should be noted that the following examples are only for illustrative purposes and should not be construed as limiting the scope of the present invention, and that the modification and modification of the present invention by those of ordinary skill in the art are not essential to the present invention.
Example 1
A conjugated compound substituted by large steric hindrance alkoxy with triarylamine as a terminal group is bridged by phenyl wrapped with dendritic alkoxy groups, and the preparation method is as follows:
into a 50mL two-necked flask were charged 0.46mmol of 4-borate-4 ',4' -dimethoxytriphenylamine (200mg), 0.21mmol of 2, 5-bis (4-t-butylbenzyloxy) -1, 4-diiodobenzene (137mg), and 0.01mmol of tetrakis (triphenylphosphine) palladium (12mg), and the system was charged with N2And thirdly, adding degassed 10mL of toluene, 2mL of ethanol and 2mL of 2mol/L potassium carbonate solution under the protection of nitrogen, refluxing at 110 ℃ for 24 hours, cooling the system to room temperature, filtering with diatomite to obtain a filtrate, spin-drying, and performing column chromatography separation to obtain 112mg of a yellow solid with the structural formula I-1, wherein the yield is as follows: 53 percent.
In the process of column chromatography separation, silica gel is 200-300 meshes, and dichloromethane and petroleum ether with the volume ratio of 1:1 are selected as eluent.
The structural formula I-1 is shown below:
elemental analysis (C)68H68N2O6): theoretical value: c, 80.92; h, 6.79. Measurement value: c, 80.81; h, 6.85.
Structural 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。
example 2
A conjugated compound substituted by large steric hindrance alkoxy with triarylamine as a terminal group is bridged by phenyl wrapped with dendritic alkoxy groups, and the preparation method is as follows:
into a 50mL two-necked flask were charged 1.71mmol of 4-borate-4 ',4' -dimethoxytriphenylamine (737mg), 0.81mmol of 1, 4-diiodobenzene protected with a dendron group (965mg), and 0.08mmol of tetrakis (triphenylphosphine) palladium (94mg), and the system was charged with N2And thirdly, adding 10mL of degassed toluene, 2mL of ethanol and 2mol/L of potassium carbonate solution under the protection of nitrogen, refluxing at 110 ℃ for 24 hours, cooling the system to room temperature, filtering (through diatomite) to obtain a filtrate, spin-drying, and performing column chromatography separation to obtain 200mg of a white solid with the structural formula I-2, wherein the yield is as follows: and 64 percent.
In the process of column chromatography separation, silica gel is 200-300 meshes, and dichloromethane and petroleum ether with the volume ratio of 1:1 are selected as eluent.
The structural formula I-2 is shown below:
elemental analysis (C)104H108N2O10): theoretical value: c, 80.80; h, 7.04. Measurement value: c, 80.91; h, 6.97.
Structural 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。
example 3
A conjugated compound substituted by large steric hindrance alkoxy with triarylamine as a terminal group is bridged by phenylethynyl wound with dendritic alkoxy groups, and the preparation method is as follows:
a50 mL two-necked flask was charged with 1.71mmol of 4-ethynyltriphenylamine (460mg), 2, 5-bis (4-tert-butylbenzyloxy) -1, 4-diiodobenzene (530mg, 0.81mmol), 0.17mmol of tetrakis (triphenylphosphine) palladium (94mg), and 0.17mmol of cuprous iodide (15mg), and the system was pumped with N2And thirdly, adding degassed tetrahydrofuran 20mL and triethylamine 10mL under the protection of nitrogen, refluxing at 80 ℃ for 24h, cooling the system to room temperature, filtering with diatomite to obtain a filtrate, spin-drying, and performing column chromatography separation to obtain 505mg of a yellow solid with a structural formula II-1, wherein the yield is as follows: 67%.
In the process of column chromatography separation, silica gel is 200-300 meshes, and dichloromethane and petroleum ether with the volume ratio of 1:2 are selected as eluent.
The structural formula II-1 is shown below:
elemental analysis (C)68H60N2O2): theoretical value: c, 87.14; h, 6.45. Measurement value: c, 87.06; h, 6.59.
Structural 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。
example 4
A conjugated compound substituted by large steric hindrance alkoxy with triarylamine as a terminal group is bridged by phenylethynyl wound with dendritic alkoxy groups, and the preparation method is as follows:
a50 mL two-necked flask was charged with 1.71mmol 4-ethynyltriphenylamine (460mg), 0.81mmol of dendrimer substituted 1, 4-diiodobenzene (965mg), 0.17mmol of tetrakis (triphenylphosphine) palladium (94mg), cuprous iodide (15mg,0.17mmol), and the system was pumped with N2And thirdly, adding degassed tetrahydrofuran 20mL and triethylamine 10mL under the protection of nitrogen, refluxing the reaction mixture at 80 ℃ for 24 hours, cooling the system to room temperature, filtering the reaction mixture through diatomite to obtain a filtrate, spin-drying the filtrate, and performing column chromatography separation to obtain 810mg of an orange solid with a structural formula II-2, wherein the yield is as follows: 68 percent.
In the process of column chromatography separation, silica gel is 200-300 meshes, and dichloromethane and petroleum ether with the volume ratio of 1:2 are selected as eluent.
The eluent is dichloromethane and petroleum ether with the volume ratio of 1: 1.
The structural formula II-2 is shown below:
elemental analysis (C)104H100N2O6): theoretical value: c, 84.75; h, 6.84. Measurement value: c, 84.90; h, 6.75.
Structural 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
The adopted equipment comprises the following steps: electrochemical workstation CHI 660D (CH Instruments Company, USA).
A glassy carbon electrode is used as a working electrode, a platinum electrode is used as a counter electrode,Ag+and the | Ag electrode is a reference electrode. At 0.001mol L-1n-Bu4NPF6CH (A) of2Cl2The solution is electrolyte, and the concentration of the measured substrate is 0.001mol L-1。
Cyclic voltammetry is usually performed at a scan rate of 100mV s-1The square wave voltammetry was measured at f ═ 10 Hz.
Data processing: the data were processed into pictures by OriginPro 8.0.
Cyclic voltammetry and square wave voltammetry tests are carried out on the dendritic alkoxy substituted conjugated organism with large steric hindrance by an electrochemical method, corresponding electrochemical parameters are obtained, and specific results are shown in table 1.
TABLE 1 electrochemical test data for the sterically hindered alkoxy-substituted conjugated compounds of examples 1-4
| Compound (I) | 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 can be seen from Table 1, the two types of compounds (I-1 and I-2 are the first type, and II-1 and II-2 are the second type) prepared by the invention both present two continuous single-electron redox processes, and the potential difference delta E value of the two redox processes obtained by testing can reach 70-240 mV. The potential difference value of the first class of compounds reaches more than 200mV, and the second class of alkyne-containing triarylamine compounds have relatively longer distance between end groups, so that the delta E value obtained by testing is relatively smaller than that of the first class of compounds. It should be clear to those skilled in the art that the above two series of compounds significantly improve the electronic mutual coupling effect between the terminal groups compared with the prior art, and have great application prospects in the field of insulating molecular wires.
Claims (5)
1. A conjugated compound substituted by large steric hindrance alkoxy with triarylamine as a terminal group is characterized in that a structural formula I is shown as follows:
wherein Ar is phenyl, R1Is OCH3，
R2Is composed of
2. A process for the preparation of a conjugated compound substituted by sterically hindered alkoxy groups which are terminated with triarylamines as claimed in claim 1, wherein the process comprises the following steps:
adding 4-borate-4 ',4' -dimethoxy triphenylamine, 2, 5-bis (4-tert-butyl benzyloxy) -1, 4-diiodobenzene and tetrakis (triphenylphosphine) palladium into a container, then adding degassed toluene, ethanol and 2mol/L potassium carbonate solution under the protection of nitrogen, refluxing for 24h at 110 ℃, cooling the system to room temperature, filtering by using diatomite to obtain filtrate, drying by spinning, and carrying out column chromatography separation to obtain the bulky alkoxy substituted conjugated compound shown as a structural formula I-1:
3. a process for the preparation of a conjugated compound substituted by sterically hindered alkoxy groups which are terminated with triarylamines as claimed in claim 1, wherein the process comprises the following steps:
adding 4-borate-4 ',4' -dimethoxy triphenylamine, dendritic group protected 1, 4-diiodobenzene and tetrakis (triphenylphosphine) palladium into a container, and pumping and filling N2Thirdly, adding degassed toluene, ethanol and 2mol/L potassium carbonate solution under the protection of nitrogen, refluxing at 110 ℃ for 24 hours, cooling the system to room temperature, filtering with diatomite to obtain filtrate, spin-drying, and performing column chromatography separation to obtain the large steric hindrance alkoxy substituted conjugated compound shown as a structural formula I-2:
4. a process for the preparation of a conjugated compound substituted by sterically hindered alkoxy groups which are terminated with triarylamines as claimed in claim 2 or 3, wherein: when the column chromatography separation is carried out, the used eluent consists of dichloromethane and petroleum ether with the volume ratio of 1:1, and the mesh number of the used silica gel is 200-300 meshes.
5. Use of a sterically hindered alkoxy-substituted conjugated compound as claimed in claim 1 in the material of insulated molecular conductors.
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