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A tetraphenylethylene terpyridine organic ligand compound, coordination supramolecule and its preparation and application

A technology of terpyridine and tetraphenylethylene, applied in organic chemistry, chemical instruments and methods, luminescent materials, etc., can solve the problems of difficult separation and purification, many reaction steps, and difficult synthesis, and achieve low synthesis difficulty and mild reaction conditions , the effect of improving yield and purity

Active Publication Date: 2021-12-10
CENT SOUTH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Most of the current methods, when the functional groups with better properties are first introduced, it is difficult to precisely control the coordination to form a preset organometallic complex. There are difficulties in synthesis, high cost, difficult separation and purification, many reaction steps and low yield. and other defects

Method used

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  • A tetraphenylethylene terpyridine organic ligand compound, coordination supramolecule and its preparation and application
  • A tetraphenylethylene terpyridine organic ligand compound, coordination supramolecule and its preparation and application
  • A tetraphenylethylene terpyridine organic ligand compound, coordination supramolecule and its preparation and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0081] Step (1) [1-(4-formaldehyde phenyl)-1,2,2-triphenyl]ethylene (500mg, 1.39mmol) and 3,4-dibromoacetophenone (930mg, 3.32mmol) Add it into a 250mL round bottom flask containing 100mL / 10mL absolute ethanol / toluene, then add NaOH (166mg, 4.17mmol), and stir overnight at room temperature. Add 20mL of ammonia water to the mixed reaction solution, add reflux for 10h, wait for the reaction solution to cool to room temperature, filter to obtain a solid, rinse with isopropanol to obtain a white solid L (1060mg), the yield is 80%. 1 H NMR (500MHz, CDCl 3 )δ8.41(s,2H,H a ),7.98-7.97(d,2H,H b ),7.83(s,2H,H c ),7.78-7.76(d,2H,H d ),7.52-7.50(d,2H,tpy-H g ),7.23-7.21(d,2H,tpy-H h ),7.17-7.07(m,19H, B,C,D,E- Ph-H).

[0082] Step (2) Add compound L (1000mg, 1.05mmol), 4-phenylboronic acid-2,2':6,2"-terpyridine (1780mg, 5.04mmol), NaOH (504mg, 12.60 mmol) and solvent THF / DMF (120:20mL), then add Pd(Ph 3 ) 4 (290mg, 0.25mmol, under the protection of nitrogen, reflux overnight a...

Embodiment 2

[0090] to containing 60mLCH 2 Cl 2 In a 100mL round bottom flask, add o-dimethoxybenzene (2g, 14.47mmol), after the o-dimethoxybenzene is completely dissolved, add liquid bromine (5.1g , 31.84mmol) of dichloromethane solution 10mL, the mixed solution was reacted at room temperature for 2h. After the reaction was completed, add a saturated aqueous solution of sodium bisulfite to quench the unreacted liquid bromine, then extract three times with water and saturated experimental water, collect the lower organic solvent, and spin dry to obtain a white solid 3 (4.2g,), The yield was 98%. 1 HNMR (500MHz, CDCl 3 )δ7.08(s,2H,ph-H),3.88(s,6H,-OCH 3 ).

[0091] Add compound 3 (3g, 10.14mmol), 4-phenylboronic acid-2,2':6,2"-terpyridine (8.5g, 24.33mmol) in a 250mL round bottom flask, NaOH (2.4g, 60.82mmol) and solvent THF (80mL), then add Pd(Ph 3 ) 4 (1.4g, 1.22mmol), under the protection of nitrogen, reflux at 80°C overnight. After the reaction was completed, the reaction liqui...

Embodiment 3

[0093] Add ligand V (10mg, 0.013mmol) and ligand R (23.8mg, 0.013mmol) to a 100mL round bottom flask, then add CH 3 OH / CH 3 CN / CHCl 3 (20mL / 20mL / 20mL), sonicate for 10min, and after the two ligands are completely dissolved, add Zn(NO 3 ) 2 Methanol solution (2mL, 49mg / 8mL), react overnight at 55°C. After the reaction was completed, the reaction liquid was cooled to room temperature, ammonium hexafluorophosphate was added and stirred for 30 minutes, and the yellow solid C 1 , yield 92%. 1 HNMR spectrum see Figure 5 , ESI-MS spectrum see Figure 6 . See NMR for purity. The complex mainly proves whether it is formed. NMR can characterize the formation and purity to a certain extent. ESI-MS can prove the existence and structural characteristics of the product.

[0094] 1 H NMR (500MHz, CD 3 CN):δ9.10-9.05(m,12H, 1,2,3-tpy- h 3',5' ),8.83-8.81(m,20H, 2,3-tpy- h 4',4” ,H b,c ),8.64-8.63(m,20H, 1-tpy- h 4',4” ),8.24-8.11(m,44H, 1,2-tpy- h g , 1,3-tpy- h 5 ',5” ...

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Abstract

The invention belongs to the technical field of supramolecular materials, and specifically discloses a tetraphenylethylene terpyridine organic ligand compound and its preparation and application. In addition, it also includes a tetraphenylethylene terpyridine organic ligand compound assembled into a rhombohedral supramolecules. The supermolecules described in the invention have good fluorescence properties.

Description

technical field [0001] The invention relates to the technical field of organic synthesis and metal coordination, in particular to a preparation method for synthesizing a terpyridine-based diamond-shaped metal organic fluorescent material through precise structure control. Background technique [0002] In the field of modern supramolecules, coordination-driven has been developed as one of the most effective methods for constructing supramolecular structures; terpyridine ligands are widely used in this field. With the development of research, the assembly is highly complex and has the function of artistic aesthetics. Sexual supramolecular structures have also received increasing attention. However, how to precisely regulate the supramolecular structure and make it have good functionality is still a difficult problem. Most of the current methods, when the functional groups with better properties are first introduced, it is difficult to precisely control the coordination to for...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/22C08G83/00C09K11/06
CPCC07D213/22C09K11/06C08G83/008C09K2211/1466C09K2211/1416C09K2211/188
Inventor 王平山王峰王俊
Owner CENT SOUTH UNIV
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