Column [5] aromatic hydrocarbon monomer and homo-polymer thereof and preparation method

A technology for homopolymers and aromatic hydrocarbons, applied in the field of polymer preparation, can solve the problems of large steric hindrance of pillar aromatic hydrocarbons, difficult polymerization, and large steric hindrance of pillar aromatic hydrocarbons.

Inactive Publication Date: 2019-06-07
EAST CHINA NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This is due to the large steric hindrance of pillar arenes, and it is difficult to achieve its polymerization by common polymerization methods.
For example, in 2013, Wang Leyong’s research group repo

Method used

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  • Column [5] aromatic hydrocarbon monomer and homo-polymer thereof and preparation method
  • Column [5] aromatic hydrocarbon monomer and homo-polymer thereof and preparation method
  • Column [5] aromatic hydrocarbon monomer and homo-polymer thereof and preparation method

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Experimental program
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Effect test

Embodiment 1

[0031] Synthesis of Compounds A-D

[0032] (1) Under nitrogen atmosphere, add p-hydroxyanisole (6.20g, 50mmol), 1,4-dibromobutane (32.40g, 150mmol), 300mL acetone into a 500mL three-necked flask and stir to dissolve, then add anhydrous carbonic acid Potassium (13.8g, 100mmol), reflux at 50°C for 24h, remove potassium carbonate by filtration, collect the filtrate and distill it under reduced pressure to obtain a yellow mucus, pass through the column with dichloromethane:petroleum ether=1:3 to obtain 10.31g of a white solid, producing Rate 80%. use 1 H NMR characterizes its structure, confirming that the white solid is compound A, and its structural formula is 1 H NMR (CDCl 3, 500MHz,298K)δ(ppm):6.83(s,4H),3.95(t,J=6.1Hz,2H),3.77(s,3H),3.49(t,J=6.7Hz,2H),2.11–2.02 (m,2H),1.92(dq,J=9.6,6.2Hz,2H).

[0033] (2) At room temperature, add 4-carboxymethyl-1,6-heptadiyne (4.08g, 30mmol), anhydrous potassium carbonate (4.14g, 30mmol), 40mL N, N-dimethyl Dimethyl formamide was sti...

Embodiment 2

[0037] Compound D, as a host molecule, can complex with guest molecules to construct a supramolecular system.

[0038] The ionic liquid pyridine bistrifluoromethanesulfonylimide salt was selected as the guest molecule, and the ionic liquid and the polymer were combined by non-covalent bonds through the host-guest complexation between the pillar arene and the guest molecule in compound D. pass image 3 From curve a) and curve b), it can be seen that when a guest molecule is added to the columnarene homopolymer, the proton H on the pyridine ring of the guest molecule c Peak disappears; proton H a The peak moves to the downfield direction, which is due to the de-shielding effect of the pillar arene cavity on the protons exposed outside the cavity; the proton H b-g The peak shifts to the high-field direction, which is due to the protons drilling into the interior of the pillar arene, which is shielded by the rich electrons in the cavity. pass 1 It can be concluded from the H N...

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Abstract

The invention discloses a column [5] aromatic hydrocarbon monomer containing a diyne functional group and a homo-polymer thereof and a preparation method. The column [5] aromatic hydrocarbon modifiedby the diyne functional group has a structure as shown in formula (I), and the homo-polymer of which the side group is the column [5] aromatic hydrocarbon has a structure as shown in formula (II). This is the first case that the column [5] aromatic hydrocarbon is modified with the diyne functional group and the column aromatic hydrocarbon polymer is obtained by a translocation cyclization polymerization method. The main chain of the polymer is polyacetylene, so that the polymer has certain conductivity; and the side group contains a large number of column aromatic hydrocarbon host molecules, so that the polymer can be further combined with guest molecules to build a supramolecular platform based on the column aromatic hydrocarbon polymer. The preparation method overcomes the difficulty that the column aromatic hydrocarbon monomer is difficult to form the homo-polymer, the polymerization time is greatly shortened, and the polymerization efficiency is improved.

Description

technical field [0001] The invention belongs to the technical field of polymer preparation, and in particular relates to a diyne functional group-modified pillar [5] arene monomer, a homopolymer thereof and a synthesis method thereof. Background technique [0002] Supramolecular chemistry is an emerging interdisciplinary subject in recent years, which has attracted the attention of more and more researchers. It is based on a variety of weak interactions, and multiple molecules use this interaction to assemble into a complex and orderly system with special functions. With the continuous in-depth study of supramolecular chemistry, scientists have successfully studied a variety of supramolecular host molecules with excellent properties, among which cyclodextrin, cucurbituril, calixarene and crown ether are well-known. Now, a new type of host molecule - pillar arene has come into people's sight. In 2008, pillar aromatics were first reported by Japanese scientist Ogoshi. It is...

Claims

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Application Information

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IPC IPC(8): C08G83/00
Inventor 廖小娟武玥赵萌侯诚昊谢美然
Owner EAST CHINA NORMAL UNIVERSITY
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