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A kind of large sterically hindered alkoxyl substituted conjugated compound with triarylamine as terminal group and its application

A technology of conjugated compounds and hindered alkoxy groups, which is applied in the field of large sterically hindered alkoxy groups substituted conjugated compounds, can solve the problems of weak electronic mutual ability, the performance of insulating molecular wires is difficult to meet the application standards, and achieves good charge transport ability. Effect

Active Publication Date: 2021-09-03
HENGYANG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, contrary to expectations, practice has proved that most of the triarylamine-terminated compounds have weak electronic interaction capabilities, and the performance of insulating molecular wires made of them is also difficult to meet the relevant application standards.

Method used

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  • A kind of large sterically hindered alkoxyl substituted conjugated compound with triarylamine as terminal group and its application
  • A kind of large sterically hindered alkoxyl substituted conjugated compound with triarylamine as terminal group and its application
  • A kind of large sterically hindered alkoxyl substituted conjugated compound with triarylamine as terminal group and its application

Examples

Experimental program
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Effect test

Embodiment 1

[0032] A large sterically hindered alkoxyl substituted conjugated compound with a triarylamine as an end group, the compound is bridged by a phenyl group entwined with a dendritic alkoxyl group, and its preparation method is as follows:

[0033] Add 0.46mmol 4-boronate-4',4'-dimethoxytriphenylamine (200mg), 0.21mmol 2,5-bis(4-tert-butylbenzyloxy)-1 to a 50mL two-necked flask , 4-diiodobenzene (137mg), 0.01mmol tetrakis (triphenylphosphine) palladium (12mg), the system was filled with N 2 Three times, and then add degassed 10mL toluene, 2mL ethanol and 2mL 2mol / L potassium carbonate solution under the protection of nitrogen, and then reflux at 110°C for 24h, the system is cooled to room temperature, filtered through diatomaceous earth to obtain the filtrate, spin Dry and separate by column chromatography to obtain 112 mg of a yellow solid with structural formula I-1, yield: 53%.

[0034] During the separation process of column chromatography, the silica gel used is 200-300 mes...

Embodiment 2

[0041] A large sterically hindered alkoxyl substituted conjugated compound with a triarylamine as an end group, the compound is bridged by a phenyl group entwined with a dendritic alkoxyl group, and its preparation method is as follows:

[0042] Add 1.71mmol 4-boronate-4', 4'-dimethoxytriphenylamine (737mg) and 0.81mmol 1,4-diiodobenzene (965mg) protected by dendrimer group into a 50mL two-necked flask, 0.08mmol tetrakis (triphenylphosphine) palladium (94mg), the system pumped N 2 Three times, then add 10 mL of degassed toluene, 2 mL of ethanol and 2 mol / L potassium carbonate solution under the protection of nitrogen, and then reflux at 110 ° C for 24 h, then cool the system to room temperature, filter (through diatomaceous earth) to obtain the filtrate, Spin-dried and separated by column chromatography to obtain 200 mg of a white solid with structural formula I-2, yield: 64%.

[0043] During the separation process of column chromatography, the silica gel used is 200-300 mesh...

Embodiment 3

[0050] A large sterically hindered alkoxyl substituted conjugated compound with triarylamine as the end group, the compound is bridged by phenylethynyl bridges with dendritic alkoxy groups, and its preparation method is as follows:

[0051] Add 1.71mmol 4-ethynyltriphenylamine (460mg), 2,5-bis(4-tert-butylbenzyloxy)-1,4-diiodobenzene (530mg, 0.81mmol), 0.17 mmol tetrakis (triphenylphosphine) palladium (94mg), 0.17mmol cuprous iodide (15mg), system pumping N 2 Three times, and then added 20 mL of degassed tetrahydrofuran and 10 mL of triethylamine under the protection of nitrogen, and then refluxed at 80 ° C for 24 h, the system was cooled to room temperature, filtered through diatomaceous earth to obtain the filtrate, spin-dried, and separated by column chromatography. 505 mg of a yellow solid of formula II-1 was obtained, yield: 67%.

[0052] During the separation process of column chromatography, the silica gel used is 200-300 mesh, and the eluent used is dichloromethane an...

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Abstract

A large sterically hindered alkoxy-substituted conjugated compound with triarylamine as the terminal group relates to the field of organic synthesis, and its structural formula I is as follows: wherein, Ar is phenyl, naphthyl or anthracenyl, R 1 for H, CH 3 or OCH 3 , R 2 It is a large hindered alkoxy chain. In the present invention, organic triarylamines with better stability are selected as redox active end groups, and conjugated ligands wrapped with dendritic alkoxy groups are used as bridge chains to synthesize a compound with large sterically hindered alkoxy chains attached. It can be seen from electrochemical tests that the terminal groups of the triarylamine conjugated compound in the present invention have extremely strong electronic interactions, and have better charge transport capability, and are especially suitable for use in insulating molecular wires.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a conjugated compound substituted with a large steric hindered alkoxy group with a triarylamine as a terminal group and an application thereof. Background technique [0002] Molecular wires are the key units for connecting molecular electronic devices and realizing the miniaturization of electronic devices. A large number of research results have shown that the charge transport ability of molecular wires decays exponentially with the increase of molecular length. Triarylamine has excellent electrochemical activity and stability. In recent years, scientists have synthesized many new compounds using it as an end group, and expect these compounds to have good charge transport ability. However, contrary to expectations, practice has proved that most of the triarylamine-terminated compounds have weak electronic interaction capabilities, and the performance of insulating molecular wire...

Claims

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Application Information

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IPC IPC(8): C07C217/86H01L51/54
CPCC07C217/86H10K85/631
Inventor 欧亚平
Owner HENGYANG NORMAL UNIV
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