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Rhombic cell containing spiral rings and synthesis method thereof

A synthesis method and cell technology, applied in the fields of nanotechnology and organic electronics, can solve the problems of toxic post-processing, large pollution, complex synthesis steps, etc., and achieve the effects of simple post-processing, high yield, and mature reaction conditions.

Inactive Publication Date: 2018-04-17
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Through reasonable molecular design, the use of Friedel-Crafts reaction has many advantages such as mild reaction conditions, high yield, high selectivity, simple post-treatment, green and non-toxic, and overcomes the complex steps of traditional ring-closed molecular synthesis, toxic post-treatment, and large pollution. question

Method used

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  • Rhombic cell containing spiral rings and synthesis method thereof
  • Rhombic cell containing spiral rings and synthesis method thereof
  • Rhombic cell containing spiral rings and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0045] Example 1: Preparation of Rhombus Cell-2a

[0046]

[0047] Add boron trifluoride ether (1ml) and 400ml 1,2-dichloroethane into a 1000ml reaction flask, stir evenly, add 1a (0.300g, 0.519mmol, 1equiv) into a container containing 100ml 1,2-dichloroethane In the constant pressure dropping funnel of ethyl chloride, drop it into the reaction bottle at a rate of one drop per second. After the dropwise addition, react for 5-10 hours. After the reaction is complete, add water to quench the reaction. Extracted with dichloromethane, collected the organic phase, dried over anhydrous magnesium sulfate, filtered off the desiccant, and distilled off the solvent under reduced pressure. The crude product was further separated and purified by silica gel chromatography to obtain white solid powder 2a (0.102g, 35.1 %).

[0048] 1 H NMR (400MHz, CD 2 Cl 2 )δ7.81–7.78(d,J=8.0Hz,4H),7.70–7.69(d,J=8.0Hz,4H),7.58–7.56(d,J=7.6Hz,2H),7.55–7.53(d ,J=7.6Hz,2H),7.50–7.47(m,3H),7.46–7.44(d,...

example 2

[0049] Example 2: Preparation of Rhombus Cell-2b

[0050]

[0051] Add boron trifluoride ether (2ml) and 900ml 1,2-dichloroethane into a 1000ml reaction flask, stir evenly, add 1b (0.600g, 1.01mmol, 1equiv) into a container containing 100ml 1,2-dichloroethane In the constant pressure dropping funnel of ethyl chloride, drop it into the reaction bottle at a rate of one drop per second. After the dropwise addition, react for 5-10 hours. After the reaction is complete, add water to quench the reaction. Extracted with dichloromethane, collected the organic phase, dried over anhydrous magnesium sulfate, filtered off the desiccant, and distilled off the solvent under reduced pressure. The crude product was further separated and purified by silica gel chromatography to obtain white solid powder 2b (0.291g, 50.0 %).

[0052] 1 H NMR (400MHz, CDCl 3 )δ7.74–7.70(t,J=7.8Hz,2H),7.65–7.59(m,4H),7.54–7.45(m,8H),7.41–7.37(m,4H),7.33–7.29(m, 6H),7.21–7.17(m,8H),7.11–7.05(m,6H),6.99–6.95...

example 3

[0053] Example 3: Preparation of Rhombus Cell-2c

[0054]

[0055] Add boron trifluoride ether (2ml) and 900ml 1,2-dichloroethane into a 1000ml reaction flask, stir evenly, add 1c (0.600g, 0.986mmol, 1equiv) into a container containing 100ml 1,2-dichloroethane In the constant pressure dropping funnel of ethyl chloride, drop it into the reaction bottle at a rate of one drop per second. After the dropwise addition, react for 5-10 hours. After the reaction is complete, add water to quench the reaction. Extract with dichloromethane, collect the organic phase, dry over anhydrous magnesium sulfate, filter off the desiccant, and distill off the solvent under reduced pressure. The crude product is further separated and purified by silica gel chromatography to obtain white solid powder 2c (0.289g, 49.6 %).

[0056] 1 H NMR (400MHz, CDCl 3 )δ7.66–7.59(m,6H),7.54–7.48(d,J=9.2,6.8Hz,8H),7.44–7.41(m,4H),7.32–7.29(d,J=10.4Hz,4H) ,7.24–7.18(d,J=8.0Hz,6H),7.11–7.09(d,J=7.6Hz,2H),7.07–7...

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Abstract

The invention relates to a rhombic cell containing spiral rings and a synthesis method thereof and belongs to the fields of nanotechnologies and organic electrons. The rhombic cell containing the spiral rings is hereinafter to be referred as the rhombic cell, is a closed-loop structure formed by connection of two types of fluorenyl groups and derivatives thereof by a manner of central symmetry, and has the distinctive characteristic of edges and corners. The structural formula of the rhombic cell is described in the specification, wherein R is a common alkyl chain. The synthesis method relatesto synthons containing the spiral rings, and forms the rhombic cell by Friedel-Crafts reaction. The rhombic cell and the synthesis method have the beneficial effects that by reasonable molecular design and utilization of the Friedel-Crafts reaction with the advantages of mild reaction condition, high yield and selectivity, simple aftertreatment and green and nontoxic effect and the like, the problems of complex steps, toxic aftertreatment and larger pollution and the like in the traditional synthesis of closed-looped molecules are overcome.

Description

technical field [0001] The invention relates to a type of spiro ring-containing rhombus cell and a synthesis method thereof, belonging to the fields of nanotechnology and organic electronics. Background technique [0002] Since the first synthesis of crown ethers by Professor Pedersen in 1967, cave ethers, spherical ethers, cyclodextrins, calixarenes and cucurbituril have been continuously synthesized. In the past decade, many macrocyclic compounds with considerable size and novel topology have been synthesized, such as pillararenes, calixarenes, cycloparaphenylene (CPP), triamylene-based macrocycles. , tetraphenylene-based macrocycles and imidazole-based macrocycles, etc. Recent studies have shown that macrocyclic compounds have multiple functions and are widely used in supramolecular chemistry, catalytic chemistry, medicinal chemistry, and materials chemistry. Therefore, novel closed-ring compounds with unique structures are important targets in the field of organic synt...

Claims

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Application Information

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IPC IPC(8): C07D495/20C07D493/10
Inventor 解令海唐磊魏颖黄维
Owner NANJING UNIV OF POSTS & TELECOMM
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