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A sterically hindered tetraphenylethylene spirochete emitting dark blue fluorescence and its synthesis method

A technology of left helix and acetic acid, applied in the field of chemistry, can solve the problems of not easy chemical modification, and the inability of tetraphenyl spirochetes to emit dark blue fluorescence.

Active Publication Date: 2022-04-29
HUAZHONG UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The invention solves the technical problem that in the prior art, the tetraphenylethylene helicoid fixed in a ring in the molecule cannot emit dark blue fluorescence, and it is not easy to carry out further chemical modification

Method used

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  • A sterically hindered tetraphenylethylene spirochete emitting dark blue fluorescence and its synthesis method
  • A sterically hindered tetraphenylethylene spirochete emitting dark blue fluorescence and its synthesis method
  • A sterically hindered tetraphenylethylene spirochete emitting dark blue fluorescence and its synthesis method

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] AIE propeller type molecule I is synthesized by the following route:

[0046]

[0047] i)98%H 2 SO 4 / AcOH / 60°C.

[0048] ii) SOCl 2 / pyridine / benzene / reflux.

[0049] iii) 245nm light / cyclohexane / N 2 / 25°C.

[0050] iv) Fuming HNO 3 / CH 2 Cl 2 / 0°C.

[0051] v) NH 2 NH 2 ·H 2 O / Pd-C / EtOH / reflux.

[0052] Add the compound of formula II (50-200g), glyoxylic acid (10-100g) and acetic acid (100-500mL) into a round bottom flask in sequence, and heat the reaction mixture to reflux for reaction, then add concentrated sulfuric acid 100-500mL under ice-bath cooling , heated and stirred for 10-50 hours, filtered, and the filtrate was extracted with dichloromethane. After the extract was washed with water and dried over anhydrous sodium sulfate, it was evaporated to dryness, and the obtained solid was recrystallized from petroleum ether to obtain a white compound of formula III with a yield of 80%.

[0053] Add the compound of formula III (10-30g), anhydrous ben...

Embodiment 2

[0061] Prepare a high-pressure liquid chromatography column with chirality, and the mobile phase is an ethanol-dichloromethane mixed solvent with a volume ratio of 80:20, and the compound of formula I (R 1 = H, R 3 =NH 2 , R 2 =CH 3 ) was split into two peaks of left helicoid and right helicoid, the retention time of peak 1 was 6.784min, and the retention time of peak 2 was 9.565min. 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 contains 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, which is called M-I; peak 2 is a right-helical body, called P-I. For the single crystal structure of the compound of formula I and M-I, see Figure 4 and Figure 5 .

Embodiment 3

[0063] In tetrahydrofuran at a concentration of 4 mg / mL, M-I(R 1 = H, R 3 =NH 2 , R 2 =CH 3 )Specific rotation[α] 20 D =+1173°; P-I(R 1 = H, R 3 =NH 2 , R 2 =CH 3 )Specific rotation[α] 20 D =-1203°.

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Abstract

The invention relates to a sterically hindered tetraphenylethylene spirochete emitting dark blue fluorescence and a synthesis method, belonging to the field of chemistry. The invention provides a method for synthesizing a tetraphenylethylene (TPE) helix and splitting it into a single left helix and a right helix. By introducing a substituent methyl group at the two ortho positions of the four phenyl groups of tetraphenylethylene, the benzene ring cannot rotate freely due to the steric hindrance of the methyl group, so that the propeller-type conformation of tetraphenylethylene is fixed. Through chiral high-pressure liquid chromatography (HPLC), making it resolved into TPE spirochete isomers. This sterically hindered TPE helicoid can emit a very difficult to obtain dark blue fluorescence, and its left-helical and right-helical enantiomers can exhibit strong circular dichroism (CD) signals and emit strong dark blue circularly polarized light ( CPL), has the potential to be used as a display material.

Description

technical field [0001] The invention belongs to the field of chemistry, and more specifically relates to a sterically hindered tetraphenylethylene helicoid that emits dark blue fluorescence and a synthesis method thereof, in particular to the synthesis, resolution and chirality of the dark blue fluorescent sterically hindered tetraphenylethylene helicoid optical properties. Background technique [0002] Enantiomerically pure chiral organic compounds not only play an important role in the production of chiral drugs, but also play an important role in the research of other chiral materials, such as chiral organic compounds with circularly polarized luminescence (CPL) activity in 3D display, Information storage and processing, encryption and anti-counterfeiting, molecular switches, biological imaging, asymmetric catalysis and other fields have important application prospects and have attracted widespread attention (Chem. Rev. 2015, 115, 11718–11940). To prepare materials with ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C211/50C07C209/32C07C209/88C07C201/12C07C205/06C07C1/20C07C15/52C07C45/89C07C49/88C07C51/353C07C57/38C09K11/06
CPCC07C211/50C07C209/325C07C209/88C07C201/12C07C1/2076C07C45/89C07C51/353C09K11/06C09K2211/1007C07B2200/13C07B2200/07C07C57/38C07C49/88C07C15/52C07C205/06Y02P30/40Y02P30/20
Inventor 郑炎松胡明
Owner HUAZHONG UNIV OF SCI & TECH
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