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Conjugated double-free-radical molecule as well as preparation method, spin distribution regulation and control method and application thereof

A free radical and conjugation technology, applied in the production of organic free radicals, organic chemistry methods, chemical instruments and methods, etc., can solve the problems of difficulty in regulating the distribution of free radical spins, complicated synthesis of conjugated biradical molecules, etc.

Active Publication Date: 2020-10-23
UNIV OF ELECTRONICS SCI & TECH OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In view of the above prior art, the present invention provides a conjugated diradical molecule and its preparation, spin distribution control method and application to solve the problems of cumbersome synthesis of conjugated diradical molecules and difficult regulation of free radical spin distribution

Method used

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  • Conjugated double-free-radical molecule as well as preparation method, spin distribution regulation and control method and application thereof
  • Conjugated double-free-radical molecule as well as preparation method, spin distribution regulation and control method and application thereof
  • Conjugated double-free-radical molecule as well as preparation method, spin distribution regulation and control method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] A kind of conjugated diradical molecule, its structure is as shown in formula (I),

[0036]

[0037] The conjugated diradical molecule in this example is prepared through the following steps:

[0038] S1: Mix 4,4-dibromoazobenzene, monomer II, tetrakis(triphenylphosphine) palladium and sodium carbonate at a molar ratio of 1:2.5:0.075:0.2, and store at 120°C in an inert gas atmosphere Condensate and reflux in a mixed solvent of tetrahydrofuran and water for 12 hours to obtain compound III. The volume ratio of water and tetrahydrofuran in the mixed solvent of tetrahydrofuran and water is 1:2; the reaction equation is as follows figure 1 shown;

[0039] S2: Dissolve compound III in dichloromethane, add lead dioxide, and react at room temperature for 30 minutes to obtain conjugated diradical molecules; the molar ratio of compound III to lead dioxide is 1:50.

Embodiment 2

[0041] A kind of conjugated diradical molecule, its structure is as shown in formula (I),

[0042]

[0043] The conjugated diradical molecule in this example is prepared through the following steps:

[0044] S1: Mix 4,4-dibromoazobenzene, monomer II, tetrakis(triphenylphosphine) palladium and sodium carbonate at a molar ratio of 1:3:0.08:0.4, and store at 115°C in an inert gas atmosphere Condensation and reflux reaction in a mixed solvent of tetrahydrofuran and water for 15h to obtain compound III, the volume ratio of water and tetrahydrofuran in the mixed solvent of tetrahydrofuran and water is 1:2; the reaction equation is as follows figure 1 shown;

[0045] S2: Dissolve compound III in dichloromethane, add lead dioxide, and react at room temperature for 25 minutes to obtain conjugated diradical molecules; the molar ratio of compound III to lead dioxide is 1:55.

Embodiment 3

[0047] A kind of conjugated diradical molecule, its structure is as shown in formula (I),

[0048]

[0049] The conjugated diradical molecule in this example is prepared through the following steps:

[0050] S1: Mix 4,4-dibromoazobenzene, monomer II, tetrakis(triphenylphosphine)palladium and sodium carbonate at a molar ratio of 1:2:0.06:0.2, and store at 125°C in an inert gas atmosphere Condensate and reflux in a mixed solvent of tetrahydrofuran and water for 12 hours to obtain compound III. The volume ratio of water and tetrahydrofuran in the mixed solvent of tetrahydrofuran and water is 1:2; the reaction equation is as follows figure 1 shown;

[0051] S2: Dissolve compound III in dichloromethane, add lead dioxide, and react at room temperature for 35 minutes to obtain conjugated diradical molecules; the molar ratio of compound III to lead dioxide is 1:40.

[0052] Result analysis

[0053] Taking Example 1 as an example, the compound III it makes carries out nuclear mag...

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Abstract

The invention discloses a conjugated double-free-radical molecule as well as a preparation method, a spin distribution regulation and control method and application of the conjugated double-free-radical molecule. The conjugated double-free-radical molecule is prepared through a one-step reaction, the preparation process is simple and convenient, consumed time is short, and the preparation method can be used for synthesizing a new double-free-radical molecule. According to the method, conjugated double-free-radical molecules are heated to regulate and control the spin distribution state of themolecules, so that the effect is remarkable, the operation is simple, the implementation is easy, and a new method is developed for regulating and controlling the spin distribution of the double-free-radical molecules.

Description

technical field [0001] The invention belongs to the technical field of special materials, and specifically relates to a conjugated diradical molecule and its preparation, spin distribution control method and application. Background technique [0002] In recent decades, diradical material molecules have attracted the attention of the scientific community. In general, conjugated diradical molecules refer to organic compound molecules with two stable long-standing unpaired electrons, and the electrons can be delocalized throughout the molecule. Due to its unique electronic structure, excellent electron transport performance and optical absorption characteristics, good redox properties, etc., it has high application value in electronic devices, nonlinear optics, organic field effect transistors, organic detection, etc. . [0003] From the perspective of quantum mechanics, as far as conjugated diradical material molecules are concerned, free radicals are not confined to a certa...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C245/08C07B60/00H01L51/05H01L51/30H01L51/42H01L51/46
CPCC07C245/08C07B61/02C07B2200/03C07B2200/13H10K85/00H10K10/46H10K30/00Y02E10/549
Inventor 郑永豪申毅熊超越葛玲兵
Owner UNIV OF ELECTRONICS SCI & TECH OF CHINA
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