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Ethynylazulenes — Building Blocks for Novel Oligoazulenes with Ethynyl and Butadiynyl Bridges

Fabian, Kai H. H. ; Elwahy, Ahmed H. M. ; Hafner, Klaus (2022)
Ethynylazulenes — Building Blocks for Novel Oligoazulenes with Ethynyl and Butadiynyl Bridges.
In: European Journal of Organic Chemistry, 2006 (3)
doi: 10.26083/tuprints-00022402
Article, Secondary publication, Publisher's Version

Abstract

The azulenes 3a,b, 6a,b, 9, 12 and 15 ethynylated in the five-membered ring were prepared by Pd-catalysed cross-coupling of the corresponding iodoazulenes 1a,b, 4a,b, 7, 10 and 13, respectively, with trimethylsilylacetylene and subsequent desilylation. The synthesis of some acyclic oligomers 23–30, 32–36 and 38–40 from these ethynylazulenes could be accomplished by oxidative Eglinton coupling as well as Pd/Cu-catalysed cross-coupling reactions with the appropriate iodoazulenes 1a,b, 4b, 31 and 34. The UV/Vis spectra of the novel oligomers 32, 35 and 36 allow an estimation of the bandgap (Eg) of poly(1,3-azulenylethynylene)s lower than 2 eV.

Item Type: Article
Erschienen: 2022
Creators: Fabian, Kai H. H. ; Elwahy, Ahmed H. M. ; Hafner, Klaus
Type of entry: Secondary publication
Title: Ethynylazulenes — Building Blocks for Novel Oligoazulenes with Ethynyl and Butadiynyl Bridges
Language: English
Date: 2022
Place of Publication: Darmstadt
Publisher: Wiley-VCH
Journal or Publication Title: European Journal of Organic Chemistry
Volume of the journal: 2006
Issue Number: 3
DOI: 10.26083/tuprints-00022402
URL / URN: https://tuprints.ulb.tu-darmstadt.de/22402
Corresponding Links:
Origin: Secondary publication service
Abstract:

The azulenes 3a,b, 6a,b, 9, 12 and 15 ethynylated in the five-membered ring were prepared by Pd-catalysed cross-coupling of the corresponding iodoazulenes 1a,b, 4a,b, 7, 10 and 13, respectively, with trimethylsilylacetylene and subsequent desilylation. The synthesis of some acyclic oligomers 23–30, 32–36 and 38–40 from these ethynylazulenes could be accomplished by oxidative Eglinton coupling as well as Pd/Cu-catalysed cross-coupling reactions with the appropriate iodoazulenes 1a,b, 4b, 31 and 34. The UV/Vis spectra of the novel oligomers 32, 35 and 36 allow an estimation of the bandgap (Eg) of poly(1,3-azulenylethynylene)s lower than 2 eV.

Uncontrolled Keywords: Azulenes / Cross-coupling / Oligoazulenes / Oxidative coupling / Palladium
Status: Publisher's Version
URN: urn:nbn:de:tuda-tuprints-224027
Classification DDC: 500 Science and mathematics > 540 Chemistry
Divisions: 07 Department of Chemistry
07 Department of Chemistry > Clemens-Schöpf-Institut > Organ Chemistry
Date Deposited: 23 Nov 2022 10:38
Last Modified: 24 Nov 2022 06:49
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