Homo- and Copolycyclotrimerization of Aromatic Internal Diynes Catalyzed with Co 2 (CO) 8 : A Facile Route to Microporous Photoluminescent Polyphenylenes with Hyperbranched or Crosslinked Architecture

This study reports the first Co (CO) -catalyzed [2+2+2] polycyclotrimerization by the transformation of internal ethynyl groups of aromatic diyne monomers. The reaction yields polycyclotrimers of polyphenylene-type with either hyperbranched or partly crosslinked architecture. The homopolycyclotrimer...

Full description

Saved in:
Bibliographic Details
Published in:Macromolecular rapid communications. 2018-02, Vol.39 (4)
Main Authors: Sedláček, Jan, Sokol, Jiří, Zedník, Jiří, Faukner, Tomáš, Kubů, Martin, Brus, Jiří, Trhlíková, Olga
Format: Article
Language:English
Subjects:
Catalysis
Diynes - chemistry
Luminescent Agents - chemical synthesis
Luminescent Agents - chemistry
Macromolecular Substances - chemical synthesis
Macromolecular Substances - chemistry
Molecular Structure
Polymerization
Polymers - chemistry
Porosity
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:This study reports the first Co (CO) -catalyzed [2+2+2] polycyclotrimerization by the transformation of internal ethynyl groups of aromatic diyne monomers. The reaction yields polycyclotrimers of polyphenylene-type with either hyperbranched or partly crosslinked architecture. The homopolycyclotrimerization of the monomers with two ethynyl groups per one molecule, namely 1,4-bis(phenylethynyl)benzene, 4,4'-bis(phenylethynyl)biphenyl, and 4-(phenylethynyl)phenylacetylene, gives partly crosslinked, insoluble polyphenylenes. The soluble, hyperbranched polyphenylenes are generated via copolycyclotrimerization of 1,4-bis(phenylethynyl)benzene with 1,2-diphenylacetylene (average number of ethynyl groups per monomer molecule < 2). This one-step polycyclotrimerization path to hyperbranched or partly crosslinked polyphenylenes is an alternative to the synthesis of these polymers by Diels-Alder transformation of substituted cyclopentadienones. All polyphenylenes prepared exhibit photoluminescence with emission maxima ranging from 381 to 495 nm. Polyphenylenes with a less compact packing of segments are microporous (specific surface area up to 159 m g ), which is particularly important in the case of soluble polyphenylenes because they can be potentially used to prepare microporous layers.
ISSN:1022-1336
1521-3927
DOI:10.1002/marc.201700518