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Method for fixing tetraphenyl ethylene (TPE) propeller conformation and splitting into single helicoids

A single, left-helical technology, applied in the chemical field, can solve the problems that the propeller structure is not easy to fix, and the helical chirality of AIE molecules has not been developed and applied.

Inactive Publication Date: 2018-03-06
HUAZHONG UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The propeller structure of most AIE compounds is the determining factor for their aggregation-induced luminescent properties, but the helical chirality of the resulting AIE molecules has not been developed and applied so far because the propeller structure is not easy to fix.

Method used

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  • Method for fixing tetraphenyl ethylene (TPE) propeller conformation and splitting into single helicoids
  • Method for fixing tetraphenyl ethylene (TPE) propeller conformation and splitting into single helicoids
  • Method for fixing tetraphenyl ethylene (TPE) propeller conformation and splitting into single helicoids

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] Tetraphenylethylene propeller type molecule I (in general formula I, X=O; R 1 = H; R 2 =H) synthesis:

[0063]

[0064] Add 0.5-2g of the compound of formula (II), 1-2g of hexamethylenetetramine and 10-50mL of trifluoroacetic acid into a round bottom flask, heat the reaction mixture under reflux for about 3 hours, and detect the reaction with TLC until the raw materials disappear. Add ice water, stir at room temperature for 2-4h, and extract with ethyl acetate. After the extracts were combined, they were dried with anhydrous sodium sulfate, filtered, and distilled under reduced pressure. The obtained crude product was separated and purified by silica gel column chromatography (eluent: ethyl acetate / petroleum ether 1:4 volume ratio), and the yellow formula (III) compound, yield 70%.

[0065] Add 200-800mg of the compound of formula (III), 300-900mg of 1,4-dibromomethylbenzene, 300-700mg of anhydrous potassium carbonate, and 50-300mL of dry acetonitrile into the rea...

Embodiment 2

[0071]Prepare a high-pressure liquid chromatography column with chirality, and the mobile phase is a dichloromethane-methanol mixed solvent with a volume ratio of 80:20. The compound of formula (I) can be resolved into two peaks, left-helical and right-helical. The retention of peak 1 The time is 2.455min, and the retention time of peak 2 is 3.430min. The percent enantiomeric excess of the two single helices of peak 1 and peak 2 is greater than 99%. Measured by single crystal x-ray diffraction, the compound of formula (I) comprises an equal amount of left-helical body and right-helical body, which is a racemate; the corresponding molecular structure of peak 1 is the left-helical body in the compound of formula (I), called It is M-I; peak 2 is right-helical, called P-I. For the single crystal structure of the compound of formula (I) and M-I, see Figure 4 with Figure 5 .

Embodiment 3

[0073] In tetrahydrofuran at a concentration of 5 mg / mL, the M-I specific rotation [α] 20 D =+479°; P-I specific rotation [α] 20 D =-502°. Absolute fluorescence quantum yield in tetrahydrofuran: formula (I) compound 79%; M-I is 94%, and P-I is also 94%; Be the absolute fluorescence quantum yield in 95:5 water / THF suspension in volume ratio: formula (I) compound 88%; M-I is 85%, P-I is also 85%.

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Abstract

The invention provides a method for fixing a tetraphenyl ethylene (TPE) propeller conformation with aggregation-induced emission (AIE), and splitting into a single left helicoid and a single right helicoid. Four phenyl groups of TPE are connected into four rings by short chains, and the TPE propeller conformation is fixed. Through a chiral preparative chromatography, the TPE propeller conformationis split into the single left helicoid and the single right helicoid. After the TPE propeller conformation is fixed, the fluorescence quantum yield is greatly improved, and fluorescence quanta have strong fluorescence in a solid state and in a solution, and show an AIE effect. The single helicoid has the specific rotation as high as 502 degrees and the strong circular dichroism effect, and can emit circularly polarized luminescence (CPL).

Description

technical field [0001] The invention belongs to the field of chemistry and relates to the fixing and splitting of tetraphenylethylene propeller structures and their chiral optical properties. Background technique [0002] Helical molecules not only have novel structures and beautiful shapes, but their helical chirality has great application prospects in physiological function regulation, chiral sensing, asymmetric catalysis, photoelectric materials, etc., and has always been a research hotspot and frontier field. (Adv. Mater. 2015, 1-16; Chem. Soc. Rev. 2013, 42, 1051-1095). In 2001, Tang Benzhong et al. discovered that the organic compound with Aggregation-Induced Emission (AIE) phenomenon has great application value in optoelectronic materials, chemical and biological sensors, etc., and has attracted extensive attention and research (Chem. Rev. 2015, 115, 11718–11940; Chem. Sci. 2015, 6, 5347–5365). The propeller structure of most AIE compounds is the decisive factor for...

Claims

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Application Information

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IPC IPC(8): C07D493/22C09K11/06
CPCC07B2200/09C07D493/22C09K11/06C09K2211/1088
Inventor 郑炎松熊加斌
Owner HUAZHONG UNIV OF SCI & TECH
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