Polyene ether compounds and preparation method thereof

A technology of compound and polyalkene ether, which is applied in the fields of polymer chemistry and material science, can solve the problems of no preparation of polyalkene ether compounds, few and few synthesis of polyalkene ether compounds, etc., and achieve the elimination of cytotoxicity and damage to materials The effect of photoelectric performance, excellent area selection type and three-dimensional selection type, simple and controllable operation

Active Publication Date: 2015-08-05
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] However, there are few reports on the addition polymerization of alkyne-hydroxyl groups in the field of organic chemistry and polymers. At present, there is no report on the preparation of polyene ethers through the "click polymerization" of alkyne-hydroxyl groups. Compared with small molecules, There are very few studies on the synthesis and application of polyalkene ether compounds

Method used

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  • Polyene ether compounds and preparation method thereof
  • Polyene ether compounds and preparation method thereof
  • Polyene ether compounds and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] (1) The first monomer binary alkynyl compound The synthesis method of is synthesized according to the synthesis method of the applicant in the published literature (Macromolecules, 2005, 38, 6382).

[0061] (2) The second monomeric dihydroxy compound direct purchase

[0062] (3) Hydroxy-alkyne polymerization to prepare polyalkene ether compounds, the structural formula is as formula (Ⅰ-1)

[0063]

[0064] Add 37.4mg (0.10mmol) of the first monomer, 22.8mg (0.10mmol) of the second monomer and 0.9mL tetrahydrofuran into a 10mL polymerization tube. After the monomers are completely dissolved, raise the temperature to 25°C. Dissolve 0.976 mg (0.008 mmol) of DMAP in 0.1 mL of tetrahydrofuran, and after the system is kept at constant temperature, add DMAP and react for 4 hours. After the reaction solution was diluted with 2 mL of tetrahydrofuran, it was added dropwise into 150 mL of rapidly stirring n-hexane through a cotton filter to obtain a pink flocculent precipi...

Embodiment 2～6

[0069] Investigated the impact of different reaction times on the click polymerization reaction among the embodiment 2~6, and raw material kind and polymerization process are all identical with embodiment 1, influence a The results are shown in Table 1.

[0070] Table 1

[0071]

[0072] a Reaction in THF in air; T=25°C; [M] 0 = 100 mM; [DMAP] = 10 mM.

[0073] b t = reaction time.

[0074] c Determined by GPC with linear polystyrene as calibrator and THF as mobile phase.

[0075] It is completely soluble in common organic solvents such as THF, chloroform, dichloromethane and DMF.

Embodiment 7～11

[0077] Embodiment 7~11 has investigated the impact of different solvents on click polymerization reaction, and raw material kind and polymerization process are all identical with embodiment 1, influence a The results are shown in Table 2.

[0078] Table 2

[0079]

[0080] a Reaction under air for 4 hours; T=25°C; [M] 0 = 100 mM; [DMAP] = 10 mM.

[0081] b Solubility (S) tested in common organic solvents such as THF, dichloromethane, toluene, chloroform and DMF: √=completely soluble; Δ=partially soluble.

[0082] c Determined by GPC with linear polystyrene as calibrator and THF as mobile phase.

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Abstract

The invention discloses a preparation method of polyene ether compounds. The method includes: organic small-molecule 4-dimethylamino pyridine (DMAP) is used as the catalyst, binary alkynyl compounds and binary hydroxy compounds are mixed with organic solvent, and the polyene ether compounds are obtained by using the click polymerization reaction of alkynyl-hydroxy. The polyene ether compounds comprise an inner unit indicated by formula (I). The polymerization step is showed in the formula (V), wherein n is larger than 1, and R1 and R2 are selected from organic groups. The method has the advantages that water and oxygen do not need to be removed during reaction, polymerization temperature is low, polymerization efficiency is high, and no metal residues exist in products; the prepared polyene ether compounds are high in steric regularity, good in machinability, and high in heat stability, degradability and aggregation-induced emission performance.

Description

technical field [0001] The invention relates to the fields of polymer chemistry and material science, in particular to a polyalkene ether compound and a preparation method thereof. Background technique [0002] Small molecule compounds containing enyl-ether bond structure widely exist in nature, such as iridoids and their derivatives which are abundant in Gentiana plants (Phyrochemistry, 1978, 17, 135-138). [0003] Organic synthesis prepares small molecules containing ene-ether linkages, usually using metal catalysts. In 2013, Niggemann's group used a calcium metal catalyst system to catalyze the cyclopropanation reaction of alkynyl and hydroxyl groups (Angew.Chem.Int.Ed., 2013, 52, 4016). In 2015, Nolan's group realized the gold-catalyzed addition reaction of intramolecular alkynyl and hydroxyl groups (ACS Catal., 2015, 5, 1330-1334). However, when metal catalysts are used, the metal residues in the system are difficult to remove, which will affect the solubility and pho...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G65/40
Inventor 史杨秦安军唐本忠汪哲孙景志
Owner ZHEJIANG UNIV
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