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An Ortho-Tetraphenylene-Based “Geländer” Architecture Consisting Exclusively of 52 sp$^{2}$-Hybridized C Atoms

Dekkiche, Hervé; Malinčik, Juraj; Prescimone, Alessandro; Häussinger, Daniel; Mayor, Marcel


A new type of “Geländer” 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 sp2-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.

Verlagsausgabe §
DOI: 10.5445/IR/1000136995
Veröffentlicht am 08.09.2021
DOI: 10.1002/chem.202101968
Zitationen: 1
Web of Science
Zitationen: 1
Zitationen: 2
Cover der Publikation
Zugehörige Institution(en) am KIT Institut für Nanotechnologie (INT)
Publikationstyp Zeitschriftenaufsatz
Publikationsdatum 15.09.2021
Sprache Englisch
Identifikator ISSN: 0947-6539, 1521-3765
KITopen-ID: 1000136995
HGF-Programm 43.32.01 (POF IV, LK 01) Molecular Materials Basis for Optics & Photonics
Erschienen in Chemistry - A European Journal
Verlag John Wiley and Sons
Band 27
Heft 52
Seiten 13258-13267
Vorab online veröffentlicht am 13.07.2021
Nachgewiesen in Dimensions
Web of Science
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