Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

A kind of helicene derivative and its preparation method and application

A technology of derivatives and helicene, which is applied in the field of helicene derivatives and their preparation, can solve problems such as low quantum yield of luminescence, difficulties in preparation and chiral resolution, easy racemization of chirality, etc., and achieve good application prospects, The effect of cheap raw materials and high racemization energy barrier

Active Publication Date: 2021-09-21
INST OF CHEM CHINESE ACAD OF SCI
View PDF0 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, at present, helicene compounds generally have problems such as low luminescence quantum yield and easy chiral racemization, while the synthesis and derivatization of higher helicenes are often limited by problems such as preparation and chiral resolution difficulties.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • A kind of helicene derivative and its preparation method and application
  • A kind of helicene derivative and its preparation method and application
  • A kind of helicene derivative and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] The reaction equation is as follows:

[0045]

[0046] 1) Add 4.75g of A and 3.66g of p-phenylboronic acid (the molar ratio of A to phenylboronic acid is 1:3) into a 250mL two-necked flask, and add 50mL of toluene, 30mL of ethanol and 20mL of 2mol / L Na 2 CO 3 Aqueous solution, add catalyst triphenylphosphine palladium 50mg (5% of the molar weight of A) after ventilating for 5 minutes, reflux for 12 hours, take the organic layer, MgSO 4 Dried, filtered, spin-dried, separated by column chromatography to obtain B 1 3.8g;

[0047] 2) In a 100mL round bottom flask, add 4.7g of B 1 , 4.9g maleic anhydride (B 1 The molar ratio of maleic anhydride to maleic anhydride is 1:5) and 50mL of xylene, heated to reflux for 10 hours, the reaction system was distilled with steam to remove xylene, and the remaining solid was dried, recrystallized with 50mL of acetic anhydride, and filtered to obtain 4.5g of anhydride addition Product C 1 ;

[0048] 3) Add 5.68g C in a 100mL rou...

Embodiment 2

[0057] The reaction equation is as follows:

[0058]

[0059] In the present embodiment 1), 2), 3) and 4) are identical with the reaction steps in " embodiment 1 ".

[0060] The structure detection result of this compound is as follows:

[0061] B 2 :HRMS(APCI)m / z calcd for C 36 h 29 f 6 o 2 [M+H] + 607.2066, found 607.2085.

[0062] C 2 :HRMS(APCI)m / z calcd for C 40 h 31 f 6 o 5 [M+H] + 705.2070, found 705.2075.

[0063] D. 2 :HRMS(APCI)m / z calcd for C 40 h 23 f 6 o 5 [M+H] + 697.1444, found 697.1452.

[0064] E. 2 :HRMS(APCI)m / z calcd for C 46 h 28 f 6 NO 4 [M+H] + 772.1917, found 772.1931.

[0065] From the above detection results, it can be seen that compound B 2 、C 2 、D 2 and E 2 structures are correct.

Embodiment 3

[0067] The reaction equation is as follows:

[0068]

[0069] In the present embodiment 1), 2), 3) and 4) are identical with the reaction steps in " embodiment 1 ".

[0070] The structure detection result of this compound is as follows:

[0071] B 3 :HRMS(APCI)m / z calcd for C 36 h 29 N 2 o 2 [M+H] + 521.2224,found 521.2235.

[0072] C 3 :HRMS(APCI)m / z calcd for C 40 h 31 N 2 o 5 [M+H] + 619.2227, found 619.2236.

[0073] D. 3 :HRMS(APCI)m / z calcd for C 40 h 23 N 2 o 5 [M+H] + 611.1601, found 611.1632.

[0074] E. 3 :HRMS(APCI)m / z calcd for C 46 h 28 N 3 o 4 [M+H] + 686.2074, found 686.2079.

[0075] From the above detection results, it can be seen that compound B 3 、C 3 、D 3 and E 3 structures are correct.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a helicene derivative, a preparation method and application thereof. The structural formula of the helicene derivative is shown in formula I-1 or formula I-2, wherein Ar is phenyl or substituted phenyl; R is an alkane with 1 to 5 carbon atoms or an alkane with 6 carbon atoms ~12 aromatics. The chiral helicene derivatives provided by the invention can be used to prepare chiral organic light-emitting materials, and the organic light-emitting materials have circularly polarized light-emitting properties. The method for preparing chiral helicene derivatives with circularly polarized luminescent properties provided by the present invention has cheap raw materials, simple synthesis method and high product yield; the helicene derivatives provided by the present invention have high racemization energy barrier and good stability And other characteristics, it has a good application prospect in the field of chiral optoelectronic materials.

Description

technical field [0001] The invention relates to a helicene derivative, a preparation method and application thereof, and belongs to the field of organic luminescent material chemistry. Background technique [0002] Helicenes are a class of polycyclic aromatic hydrocarbons with helical chirality obtained by ortho-condensation of aromatic rings. This type of polycyclic aromatic hydrocarbons has the characteristics of large π-conjugated skeleton and helical chirality, so helicene and its derivatives are widely used in the fields of organic functional materials, asymmetric catalysis, molecular recognition and assembly, etc. One of the hot spots of scientific research (Chem.Rev.2012,112,1463–1535). However, at present, helicene compounds generally have problems such as low luminescence quantum yield and easy chiral racemization, while the synthesis and derivatization of higher helicenes are often limited by difficulties in preparation and chiral resolution. Therefore, the desig...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07D209/58C09K11/06
CPCC07B2200/07C07D209/58C09K11/06C09K2211/1029
Inventor 陈传峰李猛
Owner INST OF CHEM CHINESE ACAD OF SCI
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com