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d-π-a-π-d' compound and its synthesis and application

A technology of compound and synthesis method, which is applied in the application fields of high-performance two-photon absorption and two-photon fluorescent materials, and achieves the effect of strong electronegativity

Active Publication Date: 2020-10-02
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] So far, the high-performance two-photon absorption and two-photon fluorescence materials that can truly meet the practical requirements are very limited, and a clear structure-activity relationship has not been established for this type of material. Therefore, it is necessary to design and synthesize a "large two-photon absorption Cross-section, high fluorescence quantum yield and long fluorescence lifetime" high-performance two-photon absorption and two-photon fluorescent materials have both theoretical and practical significance for promoting two-photon research and practical applications

Method used

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  • d-π-a-π-d' compound and its synthesis and application
  • d-π-a-π-d' compound and its synthesis and application
  • d-π-a-π-d' compound and its synthesis and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Example 1 Compound (Ⅲ)

[0038] Add 2.57g (6mmol) of compound (Ⅴ) and 20mL of anhydrous tetrahydrofuran to the reaction flask, and slowly add 0.84g (7.5mmol) of potassium tert-butoxide in an ice bath under the protection of nitrogen to dissolve in 30mL of anhydrous tetrahydrofuran to obtain The solution. After the dropwise addition, a solution obtained by dissolving 1.36g (5mmol) of 4-(9H-carbazol-9-yl)benzaldehyde in 20mL of anhydrous tetrahydrofuran was slowly added dropwise. Then the temperature was raised to room temperature for 8h. Then, 100 mL of distilled water was added to the reaction mixture, followed by extraction with 80 mL of dichloromethane. The obtained organic layer was dried over anhydrous magnesium sulfate, and then separated by silica gel column chromatography [eluent: V (petroleum ether): V (ethyl acetate) = 6:1] to obtain 1.19 g of yellow compound (Ⅲ) . m.p.232-234°C; 1 HNMR (DMSO-d 6 ,500MHz) δ: 8.65(s,1H), 8.27(d,J=7.8Hz,2H), 8.01(d,J=2.8Hz,...

Embodiment 2

[0039] Example 2 Compound (Ⅲ)

[0040] Add 3.21g (7.5mmol) of compound (Ⅴ) and 30mL of anhydrous tetrahydrofuran to the reaction flask, and slowly add 1.51g (13.5mmol) of potassium tert-butoxide in an ice bath under the protection of nitrogen to dissolve in 40mL of anhydrous tetrahydrofuran The resulting solution. After the dropwise addition, a solution obtained by dissolving 1.36g (5mmol) of 4-(9H-carbazol-9-yl)benzaldehyde in 20mL of anhydrous tetrahydrofuran was slowly added dropwise. Then the temperature was raised to room temperature for 16 h. Then, 100 mL of distilled water was added to the reaction mixture, followed by extraction with 80 mL of dichloromethane. The obtained organic layer was dried over anhydrous magnesium sulfate, and then separated by silica gel column chromatography [eluent: V (petroleum ether): V (ethyl acetate) = 6:1] to obtain 1.51 g of yellow compound (Ⅲ) .

Embodiment 3

[0041] Example 3 Compound (IV)

[0042] Add 2.57g (6mmol) of compound (Ⅴ) and 20mL of anhydrous tetrahydrofuran to the reaction flask, and slowly add 0.84g (7.5mmol) of potassium tert-butoxide in an ice bath under the protection of nitrogen to dissolve in 30mL of anhydrous tetrahydrofuran to obtain The solution. After the dropwise addition, a solution obtained by dissolving 0.83g (5mmol) of 3,4-dimethoxybenzaldehyde in 20mL of anhydrous tetrahydrofuran was slowly added dropwise. Then the temperature was raised to room temperature for 8h. Then, 100 mL of distilled water was added to the reaction mixture, followed by extraction with 80 mL of dichloromethane. The obtained organic layer was dried over anhydrous magnesium sulfate, and then separated by silica gel column chromatography [eluent: V (petroleum ether): V (ethyl acetate) = 5:1] to obtain 1.13 g of yellow compound (IV) . m.p.168-170℃; 1 HNMR (DMSO-d 6 ,500MHz) δ: 8.53(s,1H), 7.95(d,J=2.9Hz,1H), 7.67(d,J=16.2Hz,1H), ...

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Abstract

The invention discloses a D-pi-A-pi-D' compound as well as synthesis and application thereof. The structure of the D-pi-A-pi-D' compound is shown as formula I or formula II. The synthesis method of the D-pi-A-pi-D' compound comprises the following steps: step 1, unilateral Horner-Wadsworth-Emmons reaction is performed on 4-(9H-carbazol-9-yl)benzaldehyde or 3,4-dimethoxybenzaldehyde and a compoundshown as formula V to obtain a compound shown as formula III or formula IV; step 2, the Horner-Wadsworth-Emmons reaction is performed on 9-ethyl-9H-carbazole-3-carboxaldehyde and the compound shown asformula III or formula IV to obtain the D-pi-A-pi-D' compound shown as formula I or formula II. According to the invention, the D-pi-A-pi-D' compound has the advantages of large two-photon absorptioncross section, high fluorescence quantum yield and long fluorescence lifetime, so that the compound can be used as a high-performance two-photon absorption and two-photon fluorescence material. (Theformulas are shown in the description).

Description

[0001] (1) Technical field [0002] The present invention relates to two new D-π-A-π-D' compounds (D and D' represent different electron donors, A represents electron acceptors, and π represents conjugated bridges), synthetic methods, and their high Properties of two-photon absorption and applications of two-photon fluorescent materials. [0003] (2) Background technology [0004] Due to the limited energy density of the optical field of ordinary light, under its irradiation, molecules can only undergo linear absorption, that is, absorb a photon to reach an excited state. This process is called single-photon absorption; Photons fall back to a stable ground state, and this radiation is called single-photon fluorescence. In this photophysical process, the absorption and emission of matter follow the Stark-Einstein law. If a strong laser is used as the excitation light source, since the electric field intensity of the laser light frequency is close to the internal electric field...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/86C09K11/06
Inventor 蔡志彬郑敏董琦吉
Owner ZHEJIANG UNIV OF TECH
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