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Rigid conjugate macrocyclic compound with AIE effect as well as preparation and application of rigid conjugate macrocyclic compound

A technology of conjugated macrocycles and compounds, which is applied in the field of rigid conjugated macrocycles and their preparation and application, and can solve the problems of decreased fluorescence emission efficiency, reduced degree of radiation decay, and restricted molecular movement.

Active Publication Date: 2019-02-15
DONGHUA UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

After a lot of experimental verification and theoretical simulation, it is found that this is mainly due to the active movement of the aromatic ring in the HPS molecule relative to the central conjugated unit (aromatic ring or double bond) in the dissolved state, which dissipates the excited state energy of the molecule, making The degree of radiation decay decreases, and the fluorescence emission efficiency decreases; when the poor solvent is added, these molecules aggregate, the intramolecular movement is limited, the radiation is enhanced, and strong fluorescence occurs

Method used

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  • Rigid conjugate macrocyclic compound with AIE effect as well as preparation and application of rigid conjugate macrocyclic compound
  • Rigid conjugate macrocyclic compound with AIE effect as well as preparation and application of rigid conjugate macrocyclic compound
  • Rigid conjugate macrocyclic compound with AIE effect as well as preparation and application of rigid conjugate macrocyclic compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0073] Synthesis of compound (4e):

[0074] NaH (8.4g, 0.352mol, 4.4eq.) was added to a 500mL oblique two-necked flask, and 250mL of freshly distilled anhydrous THF and 1-dodecanol (31g, 0.167mol, 2.1eq. ), stirred at room temperature, and then added 3-chloro-2-chloromethylpropene (10g, 0.08mol, 1eq.). Finally, the temperature was raised to 65°C and reacted overnight. After the reaction solution was cooled to room temperature, ethanol was slowly added to quench the reaction, THF was removed by rotary evaporation, and the reaction solution was washed with CH 2 Cl 2 Extracted, washed with water, dried over anhydrous magnesium sulfate, filtered, concentrated, and the crude product was purified by silica gel chromatography (eluent: PE / CH 2 Cl 2 =5 / 1), 25 g of colorless liquid was obtained, yield 75%. 1 HNMR (400MHz, CDCl 3 ):δ(ppm)5.14(s,2H),3.95(s,4H),3.39(t,J=6.6Hz,4H),1.62 –1.48(m,4H),1.25(s,36H),0.87( t,J=6.7Hz,6H).

Embodiment 2

[0076] Synthesis of compound (4d)

[0077] Add 4e (5.0g, 11.78mmol) into a 100mL oblique two-necked flask. After three times of argon replacement, add 80mL freshly distilled anhydrous THF under an argon atmosphere, and slowly add THF-dissolved BH at 0°C. 3 (1mol / L, 28mL), and after stirring rapidly for 3 hours, 18mL NaOH (3mol / L) solution was added. Stir vigorously for another 15 minutes, add 18 mL of H 2 o 2 (30%), after stirring overnight at room temperature, add K 2 CO 3 to saturation, the reaction solution was subjected to CH 2 Cl 2 Extracted, washed with water, dried over anhydrous magnesium sulfate, filtered, concentrated, and the crude product was purified by silica gel column chromatography to obtain 3.5 g of a colorless liquid with a yield of 79%. 1 H NMR (400MHz, CDCl 3 ): δ(ppm)3.78(d,J=5.1,2.4Hz,1H),δ3.76(d,J=5.0Hz,1H),δ3.68(d,J=6.1Hz,1H),3.62– 3.58(m,2H),3.52(m,J=9.4,6.0Hz,2H),3.47–3.25(m,4H),2.17(s,1H),1.55(d,J=10.2,3.9Hz,4H) ,1.46–1.03(m,36H),0.99–0.74(...

Embodiment 3

[0079] Synthesis of compound (4c)

[0080] Add 4d (2g, 4.5mmol, 1eq.) and TsCl (3.91g, 22.66mmol, 5eq.) into a 100mL oblique two-necked flask. After pumping argon three times, add 60mL of anhydrous CH under argon atmosphere. 2 Cl 2 , pyridine (5.3g, 67.5mmol, 15eq.), stirred rapidly at 25°C for 5 hours, and the reaction solution was passed through CH 2 Cl 2 Extraction, combined organic phase, the organic phase was washed with 1mol / L HCl first, then washed with distilled water, dried over anhydrous magnesium sulfate, filtered, concentrated, and the crude product was purified by silica gel chromatography (eluent: CH 2 Cl 2 ), 2.2 g of light yellow liquid was obtained, and the yield was 85%. 1 H NMR (400MHz, CDCl 3 ):δ(ppm)7.81(d,J=8.3Hz,2H), 7.36(d,J=8.0Hz,2H),4.12(d,J=5.6Hz,2H),3.46–3.23(m,8H) ,2.47(s,3H),2.20(q,J=11.5,5.8Hz,1H),1.54–1.40(m,4H),1.37–1.17(m,36H),0.90(t,J=6.8Hz,6H ).

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Abstract

The invention relates to a rigid conjugate macrocyclic compound with an AIE effect as well as preparation and application of the rigid conjugate macrocyclic compound. The structural formula of the compound is (I) or (II). The preparation method comprises the following steps: taking 3,5-dibromophenol as a raw material; under alkaline condition, sequentially carrying out nucleophilic substitution onthe 3,5-dibromophenol and halohydrocarbon, carrying out Miyaura reaction on the 3,5-dibromophenol and bis(pinacolato)diboron and carrying out Suzuki coupling reaction on the 3,5-dibromophenol and 5-bromo-2-iodopyrimidine to obtain a compound 4; taking 1,4-dibromobenzophenone as the raw material, and sequentially carrying out substitution reaction, Sonogashira coupling reaction and Suzuki couplingreaction to obtain a compound 5; carrying out Suzuki coupling reaction on the compound 5 and the compound 4 to obtain a compound 3; taking off protecting groups of the compound 3 and carrying out butting cyclization to obtain the conjugate macrocyclic compound. The method has the advantages of simple operation, mature preparation process, higher yield and the like.

Description

technical field [0001] The invention belongs to the field of rigid conjugated macrocyclic compounds and their preparation and application, in particular to a rigid conjugated macrocyclic compound with AIE effect and its preparation method and application. Background technique [0002] Since the 1980s, supramolecular chemistry has experienced rapid development. Among them, the development of optoelectronic devices with different characteristics from conventional silicon and other inorganic semiconductor materials is developing rapidly, especially the design and development of materials using organic single molecules and polymers as basic constituent units of the π-electron conjugated system. more and more active. In connection with this, rigid macrocyclic compounds and their derivatives with regular structures and π-conjugated systems are attracting great attention. According to the position and orientation of the polar functional groups, this type of π-rich conjugated comp...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/22C09K11/06G01N21/64
CPCC07D487/22C09K11/06C09K2211/1007C09K2211/1044G01N21/643G01N2021/6417Y02P20/55
Inventor 张灯青杨凌辉李贤英
Owner DONGHUA UNIV
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