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Naphthalimide compound with active end and preparation method and application thereof

A naphthalimide and active end technology, which is applied in the field of naphthalimide compounds and their preparation, can solve the problems of lack of targeted modification, and achieve the effects of good luminescent performance in aggregated state, simple synthesis, and mild reaction conditions

Pending Publication Date: 2021-12-24
SHANGHAI UNIV OF ENG SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most of the existing AIE-active naphthalimide fluorescent molecules do not have the ability to further target modification (Zheng X, et al. Chemical Science 2019, 10(8): 2342-2348. Luo X, et. al. Chemical Engineering Journal, 2021, 415:129095.)

Method used

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  • Naphthalimide compound with active end and preparation method and application thereof
  • Naphthalimide compound with active end and preparation method and application thereof
  • Naphthalimide compound with active end and preparation method and application thereof

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preparation example Construction

[0052]

[0053] The preparation method of the naphthalimide compound with active end of the present invention comprises the following steps:

[0054] (a), take NH 2 -(CH 2 ) m -OH (m=1-4) or o-, m-, p-aminophenol and 4-bromo-1,8-naphthalene dicarboxylic anhydride dissolved in ethanol and reacted by heating, after the first post-treatment to obtain amides Nitrogen (N) substituted 4-bromo-1,8-naphthalimide;

[0055] (b), 4-bromo-1,8-naphthalimide substituted with nitrogen (N) on the amide obtained in step (a) and 9,9-dimethylfluorene-2-boronic acid are dissolved in a solvent, and The heating reaction is carried out under the catalyst and alkali solution, and the final target compound is obtained through the second post-treatment.

[0056] Wherein, in step (a),

[0057] When R is aminoalcohol NH 2 -(CH 2 ) m When -OH, the specific synthetic route is as follows:

[0058]

[0059] Specifically, 4-bromo-1,8-naphthalic anhydride, NH 2 -(CH 2 ) m The molar volume rati...

Embodiment 1

[0092] Embodiment 1: the synthesis of compound NIR2

[0093]

[0094] In a 250mL three-necked flask equipped with a magnetic stirring bar, 4-bromo-1,8-naphthalic anhydride (compound 1) (2.77g, 10mmol), ethanolamine (670mg, 11mmol) and 150mL ethanol were added successively, and the temperature was raised to 85 ° C, stirred and refluxed for 6h. Naturally cooled to room temperature, poured into a beaker containing 200mL of water and stirred, then left to stand and filtered with suction to obtain a filter cake, washed with saturated NaHCO 3 The solution was washed, dried in vacuo, and recrystallized with 200 mL of absolute ethanol to obtain 2.75 g of light brown powder NIR2 with a yield of 86%. 1 H NMR (400MHz, DMSO-d6) δppm 3.58-3.66(m, 2H), 4.14(t, J=6.53Hz, 2H), 4.86(t, J=6.02Hz, 1H), 8.00(t, J=7.91 Hz, 1H), 8.22 (d, J = 8.03Hz, 1H), 8.32 (d, J = 7.78Hz, 1H), 8.52-8.59 (m, 2H).

Embodiment 2

[0095] Embodiment 2: the synthesis of compound NIRF2

[0096]

[0097] At room temperature, NIR2 (1.6g, 5mmol), 9,9-dimethylfluorene-2-boronic acid (1.19g, 5mmol),

[0098] Pd(PPh 3 ) 4 (57 mg, 0.05 mmol) and 25 mL of DMF were placed in a 50 mL reaction tube. Then join K 2 CO 3 Aqueous solution 5mL (K 2 CO 3 The concentration of the solution was 1.30 mol / L), so that the solid compound was completely dissolved to obtain a brownish-red transparent solution, and the oxygen was removed by bubbling, under nitrogen protection, the temperature was gradually raised to 80° C., and the reaction was carried out for 6 hours. Naturally cooled to room temperature, poured into 100mL of water, and the filter cake obtained by suction filtration was dissolved in dichloromethane (20mL), washed with saturated brine (20mL×2), and the combined organic phase was collected, anhydrous Na 2 SO 4 After drying and spin-drying, the crude product was recrystallized with 200 mL of ethanol to obta...

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Abstract

The invention provides a naphthalimide compound with an active end and a preparation method and application thereof. The naphthalimide compound takes 1, 8-naphthalimide as an electron withdrawing body and 9, 9-dimethyl fluorene as an electron donor, the compound has aggregation-induced emission performance by changing groups at molecular amide sites, and the structural formula of the naphthalimide compound is shown in the specification, wherein R is selected from phenols or amino alcohols, the series of compounds emit weak light in a solution, but show strong green fluorescence in an aggregation state, and show an obvious aggregation-induced emission property; meanwhile, the series of compounds show fluorescence with different colors in solvents with different polarities and have an obvious solvent effect; the structure of the series of compounds has a hydroxyl active end, a probe recognition unit, a subcellular localization unit and the like can be introduced through esterification and etherification reactions, expansion in the application fields of fluorescent probes, subcellular imaging and the like is achieved, and therefore the compounds can be used for cell imaging.

Description

technical field [0001] The invention belongs to the technical field of fine chemicals, and in particular relates to a naphthalimide compound with an active end and a preparation method and application thereof. Naphthalimide dyes have important application value in the fields of fluorescence imaging, multiphoton absorption, and organic electronics. The naphthalimide compound with aggregation-induced luminescence properties proposed by the present invention improves the fluorescence and luminescence properties of the naphthalimide dyes in an aggregated state, and further improves their performance in the above-mentioned application fields. Background technique [0002] Luminescent molecules generally exhibit fluorescence quenching (Aggregation-CausedQuenching, ACQ) in the aggregated state, which greatly troubles the application prospects of luminescent molecules in the aggregated state (thin films, nano-ions) in practical applications. The Aggregation-Induced emission (AIE) m...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D221/14C09K11/06G01N21/64
CPCC07D221/14C09K11/06G01N21/6428G01N21/6456G01N21/6458C09K2211/1011C09K2211/1029
Inventor 瞿祎黄文灵吕爱风
Owner SHANGHAI UNIV OF ENG SCI
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