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Organic light-emitting nitrogen free radical molecule based on nitrogen heterocyclic structure and preparation method of organic light-emitting nitrogen free radical molecule

A nitrogen heterocycle and free radical technology, applied in the field of organic light-emitting nitrogen free radical molecules based on nitrogen heterocycle structure and its preparation, can solve the problems of restricting research and expanding applications in the field of organic light-emitting free radicals

Active Publication Date: 2022-07-29
JILIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The highly similar structure makes their emission bands and other properties not much different from each other, which greatly limits the research and application of organic light-emitting free radicals.
At the same time, there are some deficiencies in light stability, etc.

Method used

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  • Organic light-emitting nitrogen free radical molecule based on nitrogen heterocyclic structure and preparation method of organic light-emitting nitrogen free radical molecule
  • Organic light-emitting nitrogen free radical molecule based on nitrogen heterocyclic structure and preparation method of organic light-emitting nitrogen free radical molecule
  • Organic light-emitting nitrogen free radical molecule based on nitrogen heterocyclic structure and preparation method of organic light-emitting nitrogen free radical molecule

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preparation example Construction

[0052] The present invention also provides the preparation method of the organic light-emitting nitrogen radical molecule based on the nitrogen heterocyclic structure described in the above technical scheme, comprising the following steps:

[0053] Dissolve the phenylhydrazine compound shown in formula A and the compound shown in formula B, and carry out an aldehyde-aromatic hydrazine condensation reaction to obtain a hydrazone compound;

[0054] Mix the aniline compound shown in formula C, water, concentrated hydrochloric acid and sodium nitrite aqueous solution, carry out diazotization reaction, obtain diazonium salt solution;

[0055] Mixing the hydrazone compound, inorganic base, phase transfer catalyst, organic solvent and the diazonium salt solution, and carrying out a diazonium salt coupling reaction to obtain the formazan compound;

[0056] The formazan compound, barium hydroxide and benzyl bromide are mixed, and a ring closure reaction and an oxidation reaction are ca...

Embodiment 1

[0091] Example 1: Synthesis of Compound 1

[0092] first step

[0093]

[0094] Add 1.06g (5mmol) of 2,4,6-trichlorophenylhydrazine to a 100mL single-necked flask, add 20mL of methanol under stirring to form a suspension, and dropwise add 0.56mL (10mmol) of acetaldehyde (the drop rate is 15mL / min) , gradually became clear, after 2 hours of reaction, the solvent was spin-dried to obtain yellow-brown colloidal solid product 1-1, the yield was 100%.

[0095] second step

[0096]

[0097] 1.1 g (5 mmol) of p-iodoaniline, 0.93 g (5.5 mmol) of carbazole, 1.2 g (15 mmol) of nano-copper oxide were added to a 250 mL one-necked flask, and 50 mL of DMF was added. The reaction was heated at 160 °C for 36 h with stirring. After cooling, suction filtration, pour the filtrate into 500 mL of water, and add 10 g of solid sodium chloride. Stir and dissolve, let stand for 30 min, and filter with suction. Add THF to the filter cake to dissolve and spin dry. Using petroleum ether:ethyl...

Embodiment 2

[0110] Example 2: Synthesis of Compound 2

[0111]

[0112] The synthesis steps are the same as the synthesis of compound 1, except that the raw material 2,4,6-trichlorophenylhydrazine in the first step reaction is replaced with phenylhydrazine to synthesize the intermediate product 2-1, GC-MS (m / z): [M]calculated for C 8 H 10 N 2 , 134.18, found, 134.14.

[0113] The subsequent steps are the same as the synthesis of compound 1, and the product 2 is finally obtained.

[0114] Image 6 is the EPR pattern of the obtained compound 2, from Image 6 It can be seen that: peak shape, hyperfine coupling splitting characteristics and g factor value (g=2.00391) are highly similar to compound 1, and are also consistent with the EPR signal characteristics of Verdazyl radical, indicating that compound 2 is Verdazyl radical.

[0115] Figure 7 is the MALDI-TOF diagram of the obtained compound 2, from Figure 7 It can be seen: MALDI-TOF(m / z):[M]calcdfor C 33 H 26 N 5 , 492.61; ...

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Abstract

The invention belongs to the technical field of organic light-emitting materials, and provides an organic light-emitting nitrogen free radical molecule based on a nitrogen heterocyclic structure and a preparation method of the organic light-emitting nitrogen free radical molecule. The organic light-emitting nitrogen free radical molecule based on the nitrogen heterocyclic structure has a structure as shown in a formula I which is described in the specification. The center position of the organic light-emitting nitrogen free radical molecule is a six-membered nitrogen heterocyclic free radical, the six-membered nitrogen heterocyclic free radical has four nitrogen atoms, the six-membered nitrogen heterocyclic free radical is delocalized on two nitrogen atoms through resonance, and the other two nitrogen atoms and two carbon atoms can be connected with substituent groups respectively, so that the organic light-emitting nitrogen free radical molecule can be formed. The modification on organic light-emitting nitrogen free radical molecules is realized. Single electrons are delocalized on six-membered heterocycles, so that the density of the single electrons is effectively dispersed; meanwhile, as many as four nitrogen atoms exist in a six-membered heterocyclic ring, and the electronegativity of the nitrogen atoms is greater than that of carbon atoms, so that the action of single electrons and atomic nuclei is tighter than that of carbon free radicals, and the single electrons and the atomic nuclei are not easy to react with other substances, so that the stability is relatively good under an illumination condition.

Description

technical field [0001] The invention relates to the technical field of organic light-emitting materials, in particular to an organic light-emitting nitrogen radical molecule based on a nitrogen heterocyclic structure and a preparation method thereof. Background technique [0002] Room temperature organic light-emitting radical molecules have great application prospects and research value in organic light-emitting devices, fluorescence imaging, photodynamic therapy, etc., and are a new research field that has attracted much attention. However, so far, only perchlorotrityl radical (PTM) derivatives, tris(2,4,6-trichloro)benzyl, are the only stable organic light-emitting radicals that can be used for research in related fields. Radical (TTM) derivatives and bis (2,4,6-trichlorophenyl) methyl radical derivatives (BTM) and other methyl carbon radicals and their derivatives. The highly similar structures make their luminescent wavelengths and other properties not much different f...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B61/00C07D401/04C07D401/14C07D403/10C09K11/06
CPCC07B61/02C07D403/10C07D401/04C07D401/14C09K11/06C09K2211/1074C09K2211/1029
Inventor 李峰高晟翔
Owner JILIN UNIV
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