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An Ortho-Tetraphenylene-Based "Geländer" Architecture Consisting Exclusively of 52 sp2-Hybridized C Atoms
JournalArticle (Originalarbeit in einer wissenschaftlichen Zeitschrift)
 
ID 4634318
Author(s) Dekkiche, Hervé; Malincik, Juraj; Prescimone, Alessandro; Häussinger, Daniel; Mayor, Marcel
Author(s) at UniBasel Mayor, Marcel
Dekkiche, Hervé
Malincik, Juraj
Prescimone, Alessandro
Häussinger, Daniel
Year 2021
Title An Ortho-Tetraphenylene-Based "Geländer" Architecture Consisting Exclusively of 52 sp2-Hybridized C Atoms
Journal Chemistry - A European Journal
Volume 27
Number 52
Pages / Article-Number 13258-13267
Keywords bicycles, “Geländer†molecules, helical chirality, hydrocarbons, macrocyclization
Mesh terms Chromatography, High Pressure Liquid; Stereoisomerism
Abstract A new type of "Gelander" molecule based on a ortho-tetraphenylene core is presented. The central para-quaterphenyl backbone is wrapped by a 4,4'-di((Z)-styryl)-1,1'-biphenyl banister, with its aryl rings covalently attached to all four phenyl rings of the backbone. The resulting helical chiral bicyclic architecture consists exclusively of sp(2)-hybridized carbon atoms. The target structure was assembled by expanding the central ortho-tetraphenylene subunit with the required additional phenyl rings followed by a twofold macrocyclization. The first macrocyclization attempts based on a twofold McMurry coupling were successful but low yielding; the second strategy, profiting from olefin metathesis, provided satisfying yields. Hydrogenation of the olefins resulted in a saturated derivative of similar topology, thereby allowing the interdependence between saturation and physico-chemical properties to be studied. The target structures, including their solid-state structures, were fully characterized. The helical chiral bicycle was synthesized as a racemate and separated into pure enantiomers by HPLC on a chiral stationary phase. Comparison of recorded and simulated chiroptical properties allowed the enantiomers to be assigned.
Publisher Wiley
ISSN/ISBN 0947-6539 ; 1521-3765
URL https://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/chem.202101968
edoc-URL https://edoc.unibas.ch/85437/
Full Text on edoc No
Digital Object Identifier DOI 10.1002/chem.202101968
PubMed ID http://www.ncbi.nlm.nih.gov/pubmed/34254710
ISI-Number 000681381900001
Document type (ISI) Journal Article
 
   

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