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Polyene structure-containing donor-acceptor Stenhouse adduct and preparation method thereof

A technology of adducts and acceptors, which is applied in the field of donor-acceptor Steinhaus adducts containing polyene structures and its preparation, can solve the problems of high toxicity, low efficiency, and high cost, and achieve low cost, The effect of simple and convenient operation and mild reaction conditions

Inactive Publication Date: 2021-05-18
UNIV OF ELECTRONICS SCI & TECH OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In view of the deficiencies or defects in the above-mentioned prior art, the purpose of the present invention is to provide a donor-acceptor Steinhaus adduct containing a polyene structure and a preparation method thereof, which can effectively solve the problem of existing synthetic donor-acceptor adducts. The problems of high cost, low efficiency and high toxicity in the donor Steinhaus adduct technology, as well as the ability to extend the triene structure of the donor-acceptor Steinhaus adduct to tetraene and pentaene structures, enrich the Structural Scope of Donor-Acceptor Steinhaus Adducts

Method used

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  • Polyene structure-containing donor-acceptor Stenhouse adduct and preparation method thereof
  • Polyene structure-containing donor-acceptor Stenhouse adduct and preparation method thereof
  • Polyene structure-containing donor-acceptor Stenhouse adduct and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] This Example 1 provides the donor-acceptor Steinhaus adduct DASA-1 containing a polyene structure and its preparation method, and its synthesis schematic and synthesis steps are as follows:

[0042]

[0043] Step (1): Add 3-(2-furyl)acrolein (24.4mg, 0.2mmol), pyridine (0.8mg, 0.01mmol) and toluene (2.0mL) into a dry reactor, and stir at room temperature for 40 minutes , to obtain a homogeneous reaction system;

[0044] Step (2): Add Michaelis acid (57.6mg, 0.4mmol) into the reaction system obtained in step (1), and react at 60°C for 18 hours. After the reaction was completed, it was cooled to room temperature, and the solvent was removed under reduced pressure. The residue was separated and purified by silica gel column chromatography, and dried in vacuo to obtain an intermediate product (47.1 mg, yield 95%);

[0045] Step (3): Add the intermediate product (37.2 mg, 0.15 mmol), dipropylamine (15.2 mg, 0.15 mmol) and dichloromethane (2.0 mL) obtained in step (2) to ...

Embodiment 2

[0048] This Example 2 provides a donor-acceptor Steinhaus adduct DASA-2 containing a polyene structure and its preparation method, and its synthesis schematic and synthesis steps are as follows:

[0049]

[0050] Step (1): Add 3-(2-furyl)acrolein (24.4mg, 0.2mmol), pyridine (0.8mg, 0.01mmol) and toluene (2.0mL) into a dry reactor, and stir at room temperature for 30 minutes , to obtain a homogeneous reaction system;

[0051] Step (2): Add Michaelis acid (57.6mg, 0.4mmol) into the reaction system obtained in step (1), and react at 65°C for 20 hours. After the reaction was completed, it was cooled to room temperature, and the solvent was removed under reduced pressure. The residue was separated and purified by silica gel column chromatography, and dried in vacuo to obtain an intermediate product (46.6 mg, yield 94%);

[0052] Step (3): Add the intermediate product (37.2mg, 0.15mmol), N-propylaniline (20.1mg, 0.15mmol) and dichloromethane (2.0mL) obtained in step (2) to the dry...

Embodiment 3

[0055] This Example 3 provides a donor-acceptor Steinhaus adduct DASA-3 containing a polyene structure and its preparation method, and its synthesis schematic and synthesis steps are as follows:

[0056]

[0057] Step (1): Add 5-(furan-2-yl)penta-2,4-diene (29.6 mg, 0.2 mmol), pyridine (0.8 mg, 0.01 mmol) and toluene (2.0 mL) into a dry reactor ), stirred at room temperature for 40 minutes to obtain a homogeneous reaction system;

[0058] Step (2): Add Michaelis acid (57.6mg, 0.4mmol) into the reaction system obtained in step (1), and react at 60°C for 18 hours. After the reaction was completed, it was cooled to room temperature, and the solvent was removed under reduced pressure. The residue was separated and purified by silica gel column chromatography, and dried in vacuo to obtain an intermediate product (49.9 mg, yield 91%);

[0059] Step (3): Add the intermediate product (41.1 mg, 0.15 mmol), dipropylamine (15.2 mg, 0.15 mmol) and dichloromethane (2.0 mL) obtained in ...

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Abstract

The invention discloses a polyene structure-containing donor-acceptor Stenhouse adduct and a preparation method thereof, and belongs to the technical field of donor-acceptor Stenhouse adducts. According to the invention, cheap and easily available olefine aldehyde compounds are used as substrates, the cost is low, the whole synthesis route uses organic alkali as a catalyst, the yield of a target compound is improved, and the characteristics of high efficiency and low toxicity are realized; and the triene conjugated structure of a donor-acceptor Stenhouse adduct is expanded into a tetraene and pentaene structure, such that the structural range of the donor-acceptor Stenhouse adduct is substantially enriched, the photosensitive property of the donor-acceptor Stenhouse adduct is effectively regulated, and the donor-acceptor Stenhouse adduct can be applied to more fields, and has scientific and practical values.

Description

technical field [0001] The invention relates to the technical field of a donor-acceptor Steinhaus adduct containing a polyene structure, in particular to a donor-acceptor Steinhaus adduct containing a polyene structure and a preparation method thereof. Background technique [0002] Donor-acceptor Steinhaus adducts are emerging light-sensitive molecules in recent years, which are mainly composed of three parts: electron acceptor part, electron donor part and triene conjugated п bridge part. Donor-acceptor Steinhaus adducts can undergo isomerization from chain to ring under the action of external visible light stimulation, and can undergo reverse isomerization from ring to chain under the action of heating change. The isomerization process of the donor-acceptor Steinhaus adduct can be controlled by adjusting the external light, so that the donor-acceptor Steinhaus adduct molecule is mainly in the geometric configuration, molecular polarity and electronic distribution. A reve...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D319/06C07D239/60C07C225/18C07C221/00C09D11/50
CPCC07B2200/09C07C221/00C07C225/18C07D239/60C07D319/06C09D11/50C07C2602/08
Inventor 王东升段永丽毛礼俊王真郑永豪
Owner UNIV OF ELECTRONICS SCI & TECH OF CHINA
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