Eureka AIR delivers breakthrough ideas for toughest innovation challenges, trusted by R&D personnel around the world.

Preparation method of benzophenanthrene-pyrene-benzophenanthrene discotic liquid crystal triad compound

A discotic liquid crystal, triphenylene technology, applied in the field of discotic liquid crystal triplet compounds

Active Publication Date: 2021-06-18
SICHUAN NORMAL UNIVERSITY
View PDF5 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are still a few reports on pyrene extending the p-conjugated coplanarity by coupling with triphenylene perfluorobutanesulfonate to form organic functional materials with both liquid crystallinity and luminescence.

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
  • Preparation method of benzophenanthrene-pyrene-benzophenanthrene discotic liquid crystal triad compound
  • Preparation method of benzophenanthrene-pyrene-benzophenanthrene discotic liquid crystal triad compound
  • Preparation method of benzophenanthrene-pyrene-benzophenanthrene discotic liquid crystal triad compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] The compound provided in this example is an intermediate (c) of the compound in general formula (I), and its preparation reaction is as follows:

[0041]

[0042] Using pyrene (1.0 g, 4.944 mmol) as raw material, it was mixed with bis-linked pinacol borate (2.763 g, 10.88 mmol), [Ir(OMe)COD] 2 (0.1707 g, 0.2472 mmol) and dtbpy (0.1354 g, 0.4944 mmol) molar pyrene: double pinacol borate: [Ir(OMe)COD] 2 : dtbpy= 1 : 2.2 : 0.05 : 0.1 was weighed into a 100 ml reaction tube and 30 ml cyclohexane was added, under the protection of nitrogen, reacted at 80°C for 16 h, cooled to room temperature after the reaction, Chloromethane for extraction, organic phase with anhydrous MgSO 4 dried, filtered, spin-dried, and subjected to silica gel column chromatography (eluent: V 二氯甲烷 :V 石油醚 =1:1), recrystallized from ethyl acetate and ethanol to obtain white crystals (c) (1.4 g, yield 62%) .

[0043] H NMR 1 H NMR (CDCl 3 , TMS, 400 MHz), δ:8.62(s, 2H, ArH), 8.08(s, 4H,ArH), 1.46...

Embodiment 2

[0045] The compound provided in this example is R 1 and R 2 Both are -C 6 h 13 Intermediate (b) , Its preparation reaction is as follows:

[0046]

[0047] Starting from 3,6,7,10,11-penta(hexyloxy)-2-hydroxytriphenylene (a) (3.0 g, 4.03 mmol), it was mixed with triethylamine (4.07 g, 40.3 mmol) Weigh it in a 50ml reaction tube at a molar ratio of 1:10, add 20 ml of dichloromethane dried with sintered anhydrous calcium chloride, degas and protect with nitrogen at a temperature of -50°C, and then Then, perfluorobutylsulfonyl fluoride (3.65 g, 12.1 mmol) was added slowly according to the molar ratio of compound (a) and perfluorobutylsulfonyl fluoride being 1:3, and then the reaction was returned to room temperature for 20 h. After the reaction was finished, extract with dichloromethane, and the organic phase was extracted with anhydrous MgSO 4 dried, filtered, spin-dried, and subjected to silica gel column chromatography (eluent: V 二氯甲烷 :V 石油醚 =1:3) separated and purif...

Embodiment 3

[0050] This example provides the preparation of the compound of general formula (I), wherein R 1 and R 2 Both are -C 6 h 13 , the preparation reaction is as follows:

[0051]

[0052] Weigh (c) (100 mg, 0.2202 mmol), (b) (633.3 mg, 0.6165 mmol), K 2 CO 3 (912.8 mg, 6.605 mmol) and Pd(PPh 3 ) 4 (50.89mg, 0.044 mmol) in a 50 ml reaction tube and add mixed solvent water (3 ml) / THF (10 ml), under the protection of nitrogen, react at 70 ℃ for 48 h, cool to room temperature after the reaction, use Dichloromethane was extracted, and the organic phase was extracted with anhydrous MgSO 4 dried, filtered, spin-dried, and subjected to silica gel column chromatography (eluent: V 二氯甲烷 :V 石油醚 =1:2, recrystallized with ethyl acetate and ethanol to obtain white solid (I) (249.6 mg, yield 68%).

[0053] H NMR 1 H NMR (CDCl 3 , TMS, 400 MHz), δ:8.62(s, 2H, ArH), 8.54(s, 4H,ArH), 8.18(s, 4H, ArH), 8.03(s, 2H, ArH), 7.97(s, 4H , ArH), 7.89(s, 4H, ArH),4.22-4.29(m, 20H, OCH 2 ), 1...

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 relates to synthesis of a discotic liquid crystal triad compound containing a plurality of alkoxy chains and based on 2,7-bis(3,6,7,10,11-penta(alkoxy)benzophenanthren-2-yl)pyrene. The synthesis is characterized in that the discotic liquid crystal triad compound has a structure as shown in a general formula (I), wherein R1 is a C6-C10 alkyl chain, and R2 is a C1-C10 alkyl chain. The compound shown in the general formula (I) can be self-assembled into a hexagonal columnar liquid crystal intermediate phase and a nematic phase within a wide temperature range. The invention further provides the preparation method of the discotic liquid crystal triad compound containing the multiple alkoxy chains and based on the 2,7-bis(3,6,7,10,11-penta(alkoxy)benzophenanthren-2-yl)pyrene, and the preparation method is simple and rapid in synthetic route, mild in condition and high in yield of the discotic liquid crystal triad compound containing.

Description

technical field [0001] The invention relates to a discotic liquid crystal triplet compound of 2,7-bis(3,6,7,10,11-penta(alkoxy)triphenylene-2-yl)pyrene and a preparation method thereof. Background technique [0002] Discotic liquid crystals are a unique class of materials that have remarkable electrical and photoconductive properties and can form nano-microstructures through self-assembly. Discotic liquid crystal molecules usually consist of two basic components: a rigid planar or near-planar aromatic core surrounded by flexible aliphatic side chains. Such discotic molecules can spontaneously self-assemble in the liquid crystal phase, and form an ordered nematic phase or an ordered columnar phase and lamellar phase through the interaction of π-π bonds between benzene rings. This offers unique possibilities for one-dimensional charge-carrier systems, where the interaction of electrons and the influence of electron mobility rates make their stacking period along the column mu...

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): C07C43/20C07C303/28C07C309/65C07F5/02C07C41/30C09K11/06C09K19/32H01L51/05
CPCC07C43/20C07C303/28C07F5/025C07C41/30C09K11/06C09K19/32C09K2211/1011C07C2603/42C07C2603/50H10K10/46C07C309/65
Inventor 刘帅赵可孝赵可清胡平汪必琴
Owner SICHUAN NORMAL UNIVERSITY
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Eureka Blog
Learn More
PatSnap group products