Thermally stable Diels–Alder polymer using an azodicarbonyl compound as the dienophile

A novel Diels–Alder polymerization system was developed, using an azodicarbonyl compound as the dienophile. A bis(azodicarbonyl) monomer was prepared by quantitative oxidation of bis(diacylhydrazine) with tBuOCl in the presence of pyridine. Diels–Alder polymerization was carried out with a bisdiene...

Full description

Saved in:
Bibliographic Details
Published in:Polymer (Guilford) 2019-03, Vol.167, p.60-66
Main Authors: Sakurai, Masayoshi, Kihara, Nobuhiro
Format: Article
Language:English
Subjects:
Azodicarbonyl compound
Diels–Alder polymerization
Monomers
Oxidation
Ozonolysis
Polymerization
Polymers
Pyridines
Thermal stability
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A novel Diels–Alder polymerization system was developed, using an azodicarbonyl compound as the dienophile. A bis(azodicarbonyl) monomer was prepared by quantitative oxidation of bis(diacylhydrazine) with tBuOCl in the presence of pyridine. Diels–Alder polymerization was carried out with a bisdiene monomer, using AgOTf as the catalyst. High thermal stability of the polymer is characteristic for the products of this Diels–Alder polymerization system, in which the Diels–Alder reaction is irreversible. The C=C bond in the Diels–Alder polymer can be cleaved by ozonolysis to give a polyketone. [Display omitted] •Diels–Alder polymerization using an azodicarbonyl compound as the dienophile is effectively catalyzed by silver triflate.•Diels–Alder polymer obtained from the azodicarbonyl monomer is thermally stable.•C=C double bond in the Diels–Alder polymer can be cleaved without decrease of molecular weigh of the polymer.
ISSN:0032-3861
1873-2291
DOI:10.1016/j.polymer.2019.01.071