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Space-conjugated organic molecule based on hexaarylbenzene skeleton and preparation and application thereof

A technology of hexaarylbenzene and organic molecules, which is applied in the field of organic molecules with steric conjugation effects and its preparation, can solve the problems of blocked charge transmission channels, and the conductivity of rod-shaped molecules has not reached industrial application, achieving simple structure, Excellent effect, the effect of improving electrical conductivity

Active Publication Date: 2018-11-06
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, rod-like molecules based on valence bond conjugation mainly transport charges through the highly delocalized π orbitals on their skeletons. When the skeleton breaks, the charge transfer channel is blocked. In addition, the conductivity based on rod-like molecules is far from reaching industrial applications. needs

Method used

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  • Space-conjugated organic molecule based on hexaarylbenzene skeleton and preparation and application thereof
  • Space-conjugated organic molecule based on hexaarylbenzene skeleton and preparation and application thereof
  • Space-conjugated organic molecule based on hexaarylbenzene skeleton and preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Embodiment 1: Preparation of spatially conjugated organic molecule [HP(OMe)B-SMe] based on hexaarylbenzene:

[0041]

[0042] Reaction equation (1):

[0043]

[0044]

[0045] (1) Add dicyclohexylcarbodiimide (DCC) (6.19g, 30mmol) and 4-dimethylaminopyridine (916mg, 7.5mmol) to the reaction vessel, pump and exchange gas three times, add dichloromethane under nitrogen atmosphere Methane 60mL, dropwise add a dichloromethane solution (dichloromethane 60mL) of 4-bromophenylacetic acid (compound 1, 30mmol), continue to react for 24 hours after the dropwise addition, concentrate to remove the solvent after the reaction is completed, and separate by column chromatography The intermediate product 2 (compound 2) was obtained by purification with a yield of 60%;

[0046] (2) Add intermediate product 2 (3.69g, 10mmol), 4,4'-dimethoxyphenol ester (compound 3) (2.7g, 10mmol) and potassium hydroxide (0.168g, 3mmol) into the reaction flask , pumped and changed three times, ...

Embodiment 2

[0050] Example 2: Spatically conjugated organic molecules based on hexaarylbenzene [HP(OMe) 3 Preparation of B-SMe]

[0051]

[0052] Reaction equation (2):

[0053]

[0054] (1) Add raw material 1 (1-bromo-3,4,5-trimethoxybenzene) (2.47g, 10mmol), raw material 2 (butynedic acid) (0.57g, 5mmol), bis(triphenylphosphine ) palladium dichloride (0.35g, 0.5mmol), 1,4-bis(diphenylphosphine)butane (0.21g, 0.5mmol), 1,8-diazabicyclo[5.4.0]undecane -7-ene (1.52g, 10mmol) was added to the reaction flask, pumped and ventilated three times, added 60mL dimethyl sulfoxide solvent, and reacted at 115°C for 12 hours. After the reaction was completed, poured into 200mL distilled water and dichloromethane Three times, washed three times with water, dried, and the solvent was removed by rotary evaporation, separated and purified by column chromatography to obtain a light yellow intermediate product 3 (compound 3), with a yield of 55%;

[0055] (2) Add intermediate product 3 (1.79g, 5mmo...

Embodiment 3

[0061] Example 3: Sterically conjugated organic molecules based on hexaarylbenzene [HP 2 T 2 Preparation of B-SMe]

[0062]

[0063] Reaction equation (3):

[0064]

[0065](1) Add dicyclohexylcarbodiimide (DCC) (6.19g, 30mmol) and 4-dimethylaminopyridine (916mg, 7.5mmol) to the reaction vessel, pump and exchange gas three times, add dichloromethane under nitrogen atmosphere Methane 60mL, dropwise add a dichloromethane solution (dichloromethane 60mL) of 4-bromophenylacetic acid (compound 1, 30mmol), continue to react for 24 hours after the dropwise addition, concentrate to remove the solvent after the reaction is completed, and separate by column chromatography Purified to obtain intermediate product 2 with a yield of 60%;

[0066] (2) Add intermediate product 2 (3.69g, 10mmol), thienoin (compound 3) (2.2g, 10mmol) and potassium hydroxide (0.168g, 3mmol) into the reaction flask, pump and change gas three times, under nitrogen protection Inject solvent ethanol (30mL),...

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Abstract

The invention belongs to the technical field of organic electronics, and discloses a space-conjugated organic molecule based on a hexaarylbenzene skeleton and preparation and application thereof. Thespace-conjugated organic molecular structure based on the hexaarylbenzene skeleton is Formula I, wherein m and n are each an integer greater than 0; Ar1 is same or different aryl and / or heteroaryl; Ar2 is same or Different aryl and / or heteroaryl; R is-CN,-N=C=O,-N=C=S,-Se-CH3,-S-CH3,-NO2,-COOH or-NH2. The space-conjugated organic molecule has both spatial conjugation and valence bond conjugation effects, has multiple conductive channels, not only can significantly improve the molecular conductance, but also can greatly compensate for a low conductance phenomenon caused by insufficient valence-bond conjugated effects. The space-conjugated organic molecule is easy to prepare and has very good application prospects in the field of organic optoelectronics.

Description

technical field [0001] The invention belongs to the technical field of organic electronics, and in particular relates to an organic molecule with space conjugation effect and its preparation method and application. Background technique [0002] In recent years, with the rapid development of large-scale integrated circuit technology, traditional electronic devices have approached the limit of manufacturing both in theory and in processing technology. Research on nanoelectronics based on molecular electronic devices is expected to solve this problem. Molecular wires, as the basic components of molecular electronic devices, have become a research hotspot in the interdisciplinary field. Most of the widely studied organic molecular wires are rod-shaped molecules based on valence bond conjugation, such as oligobenzene, oligostyrene, and oligothiophene. However, rod-like molecules based on valence bond conjugation mainly transport charges through the highly delocalized π orbitals...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C323/18C07C319/20C07D333/18
CPCC07C323/18C07D333/18
Inventor 唐本忠赵祖金甄士杰陈龙秦安军胡蓉蓉王志明
Owner SOUTH CHINA UNIV OF TECH
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