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Nuclear parent substituted naphthalimide electrochemical polymerization monomer and preparation method thereof

A kind of technology of naphthalenediimide and naphthalenediimide mother, which is applied in the field of electrochemical polymerization monomer of naphthalenediimide substituted by mother nucleus and preparation thereof

Pending Publication Date: 2022-03-04
FUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The purpose of the present invention is to provide three types of preparation methods for the electrochemical polymerization of mother-core substituted naphthalene diimides in view of the current problems in the application of mother-core substituted naphthalene diimides in the field of organic optoelectronics

Method used

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  • Nuclear parent substituted naphthalimide electrochemical polymerization monomer and preparation method thereof
  • Nuclear parent substituted naphthalimide electrochemical polymerization monomer and preparation method thereof
  • Nuclear parent substituted naphthalimide electrochemical polymerization monomer and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Synthesis of compound PNDI-Cz:

[0038]A mixture of PNDI (0.5 g, 1.2 mmol), Cz-E284 (3.6 g, 12.4 mmol), anhydrous copper acetate (2.2 g, 12.4 mmol), well-dried molecular sieves (4 Å) and anhydrous N,N-di A suspension of methylacetamide (50 mL) was continuously sparged with oxygen for 30 min, then triethylamine (1.7 mL, 12.4 mmol) was added to the suspension and the resulting reaction mixture was stirred at 55 °C under an oxygen atmosphere for 2 days . During this period, it is necessary to ensure that the oxygen content of the system is sufficient to ensure the smooth progress of the reaction. Then additional Cz-E284 (1.8 g, 6.2 mmol), anhydrous copper acetate (1.1 g, 6.2 mmol) and triethylamine (0.9 mL, 6.2 mmol) in N,N-dimethylacetamide (15 mL ) solution was added to the reaction mixture, which was stirred for another 3 days at 55 °C under an oxygen atmosphere. After 5 days, the reaction mixture was cooled to room temperature, washed with a small amount of DMF, fol...

Embodiment 2

[0041] Synthesis of compound PNDI-TPA:

[0042] A mixture of PNDI (0.5 g, 1.2 mmol), TPA-E284 (3.6 g, 12.4 mmol), anhydrous copper acetate (2.2 g, 12.4 mmol), well-dried molecular sieves (4 Å) and anhydrous N,N-dimethyl A suspension of acetamide (50 mL) was continuously sparged with oxygen for 30 min, then triethylamine (1.7 mL, 12.4 mmol) was added to the suspension and the resulting reaction mixture was stirred at 55 °C under an oxygen atmosphere for 2 days. During this period, it is necessary to ensure that the oxygen content of the system is sufficient to ensure the smooth progress of the reaction. Then additional amounts of TPA-E284 (1.8 g, 6.2 mmol), copper acetate (1.1 g, 6.2 mmol) and triethylamine (0.9 ml, 6.2 mmol) in N,N-dimethylacetamide (15 ml) solution was added to the reaction mixture, at O 2 Stir at ambient for an additional 3 days at 55°C. After 5 days, the reaction mixture was cooled to room temperature and washed with CH 2 Cl 2 (100 mL) for washing. Af...

Embodiment 3

[0045] Synthesis of compound PNDI-2CZ:

[0046] A mixture of PNDI (0.5 g, 1.2 mmol), 2Cz-E284 (5.6 g, 12.4 mmol), anhydrous copper acetate (2.2 g, 12.4 mmol), well-dried molecular sieves (4 Å) and anhydrous N,N-dimethyl A suspension of acetamide (50 mL) was continuously sparged with oxygen for 30 min, then triethylamine (1.7 mL, 12.4 mmol) was added to the suspension and the resulting reaction mixture was stirred at 55 °C under an oxygen atmosphere for 2 days. During this period, it is necessary to ensure that the oxygen content of the system is sufficient to ensure the smooth progress of the reaction. Then an additional amount of 2Cz-E284 (2.8 g, 6.2 mmol), copper acetate (1.1 g, 6.2 mmol) and triethylamine (0.9 ml, 6.2 mmol) in N,N-dimethylacetamide (25 ml) solution was added to the reaction mixture, at O 2 Stir at ambient for an additional 3 days at 55°C. After 5 days, the reaction mixture was cooled to room temperature and washed with CH 2 Cl 2 (100 mL) for washing. ...

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Abstract

The invention discloses a parent nucleus substituted naphthalimide electrochemical polymerization monomer and a preparation method thereof. According to the invention, a series of D-pi-A (donor-pi-acceptor) type organic dye molecules which take parent nucleus substituted naphthalimide as an acceptor and take triphenylamine or carbazole or thiophene and other elements with electrochemical polymerization activity as donors are synthesized. The electron cloud distribution and molecular orbital energy level distribution of the naphthalimide are adjusted through different parent nucleus substituents. The synthesized D-pi-A (donor-pi-acceptor) type organic dye molecule has excellent oxidation-reduction activity, and can form a thin film through electrochemical polymerization to be applied to the photoelectric field.

Description

technical field [0001] The invention belongs to the technical field of photoelectric functional materials, and in particular relates to a mother core substituted naphthalene diimide electrochemically polymerized monomer and a preparation method thereof. Background technique [0002] As the smallest homologue of aryldiimide, naphthalene diimide (NDI) has the advantages of high electron affinity, good carrier mobility, good thermal stability and oxidation stability, and its structural characteristics are relatively The large conjugated system and delocalized π electrons are easily excited due to changes in external conditions, and its central structure has four carbonyl groups, which strongly pull electrons to make the central naphthyl core in an electron-deficient state. Due to the electron-deficient nature of the naphthalene diimide central nucleus, the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) can be effectively changed by ...

Claims

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Application Information

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IPC IPC(8): C07D471/06C09K9/02C25D9/02
CPCC07D471/06C09K9/02C25D9/02C09K2211/1466
Inventor 郭智勇江神通罗雅方武嘉雯
Owner FUZHOU UNIV
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