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Neutral cross-conjugated biradical based on intramolecular ion pair and preparation method of neutral cross-conjugated biradical

A cross-conjugation and free-radical technology, applied in the field of neutral cross-conjugated double-radical and its preparation, can solve the problems of hindering the research and application of double-radical molecules, difficult separation and crystallization, complicated reaction process, etc. The effect of simple and reliable route, simple preparation method and broad application prospect

Pending Publication Date: 2022-07-29
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these examples show that the PCET strategy can only form cationic diradicals, and the reaction process is complicated, the yield is low, and it is difficult to separate and crystallize, thus hindering the further research and application of diradical molecules

Method used

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  • Neutral cross-conjugated biradical based on intramolecular ion pair and preparation method of neutral cross-conjugated biradical
  • Neutral cross-conjugated biradical based on intramolecular ion pair and preparation method of neutral cross-conjugated biradical
  • Neutral cross-conjugated biradical based on intramolecular ion pair and preparation method of neutral cross-conjugated biradical

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] In a glove box, the neutral precursor (R1~R4 are all H) (0.2mmol, 136.6mg), tris(pentafluorophenyl)borane (209.9mg, 0.41mmol) and 25mL of anhydrous and oxygen-free toluene were placed In a 100 mL Schlenk bottle, the mixture was heated to 135° C. under a nitrogen atmosphere and stirred for 12 h under reflux. After the reaction is over, filter through an organic filter to obtain a yellow-brown solution and concentrate it to about 15 mL, add an appropriate amount of n-hexane, and then place it at -40°C for low-temperature crystallization, and finally obtain a solution suitable for single crystal X-ray diffraction. Dark yellow crystals. Yield: 91.75 mg, 34.9%.

[0046] The result is as Figure 1-3 shown, figure 1 is the crystal structure of the synthesized neutral bis(triarylamine) diradical, which shows the formation of two planar five-membered B-heterocycles bridged by a benzene ring containing a donor group-bis(triarylamine) unit . C in the crystal 6 O 4 B 2 The ...

Embodiment 2

[0054] In the glove box, the neutral precursors (R1~R4 are all CH 3 ) (0.2 mmol, 147.8 mg), tris(pentafluorophenyl) borane (209.9 mg, 0.41 mmol) and 25 mL of anhydrous and oxygen-free toluene were placed in a 100 mL Schlenk flask, heated to 140 ° C under nitrogen atmosphere and stirred for reaction 48h. After the reaction is over, filter through an organic filter to obtain an orange-yellow solution and concentrate it to about 15 mL, add an appropriate amount of n-hexane, and then place it at -40°C for low-temperature crystallization, and finally obtain a solution suitable for single crystal X-ray diffraction. Orange-yellow crystals. Yield: 96.22 mg, 35.1%.

[0055] The result is as Figure 4-6 shown, Figure 4 is the crystal structure of the synthesized neutral bis(triarylamine) diradical, it can be seen that two planar five-membered B- Heterocycle. C in the crystal 6 O 4 B 2 The dihedral angle between the plane of the unit and the plane of the adjacent benzene ring i...

Embodiment 3

[0063] In a glove box, the neutral precursor (R1~R4 are all tBu) (0.2mmol, 170.2mg), tris(pentafluorophenyl)borane (209.9mg, 0.41mmol) and 25mL of anhydrous and oxygen-free toluene were placed In a 100 mL Schlenk bottle, the reaction was heated to 150° C. under a nitrogen atmosphere and stirred for 36 h. After the reaction is over, filter through an organic filter to obtain a dark yellow solution and concentrate it to about 15 mL, add an appropriate amount of n-hexane, and then place it at -40°C for low-temperature crystallization, and finally obtain a solution suitable for single crystal X-ray diffraction. Dark yellow crystals. Yield: 88.95 mg, 28.9%.

[0064] The result is as Figure 7-8 shown, Figure 7 is the crystal structure of the synthesized neutral bis(triarylamine) diradical, it can be seen that two planar five-membered B- Heterocycle. C in the crystal 6 O 4 B 2 The dihedral angle between the plane of the unit and the plane of the adjacent benzene ring is app...

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Abstract

The invention discloses an intramolecular ion pair-based neutral cross-conjugated biradical and a preparation method thereof, and the preparation method comprises the following step: reacting a neutral precursor and Lewis acid in an organic solvent under the protection of inert gas. The synthesis method is simple and reliable, not only opens up a new way for constructing neutral double free radicals, but also provides a new opportunity for potential application of Lewis acid in the field of free radical chemistry.

Description

technical field [0001] The invention belongs to the field of organic radical synthesis, in particular to a neutral cross-conjugated double radical based on intramolecular ion pairs and a preparation method thereof. Background technique [0002] Diradicals, i.e. molecules containing two unpaired electrons, are one of the most interesting research topics in contemporary free radical chemistry, not only of great significance for understanding the nature of chemical bonds, but also in organic spintronics, nonlinear optics, Organic electronic devices, light-emitting diodes, solar cells, organic magnets and other fields play an important role. In general, the biradicals with carbon atoms as spin centers are extremely unstable, but when carbon atoms are replaced by nitrogen atoms, more stable bis(triarylamine) biradicals can be obtained by oxidation. Over the past few decades, scientists have successfully isolated a number of bis(triarylamine) diradical dications, which can be con...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B60/00C07F5/02C07F5/06
CPCC07B61/02C07F5/02C07F5/069C07B2200/03C07B2200/13
Inventor 王新平王杰
Owner NANJING UNIV
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