Bicyclic Phenyl-Ethynyl Architectures: Synthesis of a 1,4-Bis(phenylbuta-1,3-diyn-1-yl) Benzene Banister.

Autor: Bannwart LM; Department of Chemistry, University of Basel, St. Johanns-Ring 19, 4056, Basel, Switzerland., Müntener T; Biozentrum, University of Basel, Klingelbergstrasse 70, 4056, Basel, Switzerland., Rickhaus M; Department of Chemistry, University of Zurich, Winterthurerstrasse 190, 8057, Zurich, Switzerland., Jundt L; Department of Chemistry, University of Basel, St. Johanns-Ring 19, 4056, Basel, Switzerland., Häussinger D; Department of Chemistry, University of Basel, St. Johanns-Ring 19, 4056, Basel, Switzerland., Mayor M; Department of Chemistry, University of Basel, St. Johanns-Ring 19, 4056, Basel, Switzerland.; Institute for Nanotechnology (INT), Karlsruhe Institute of Technology (KIT), P. O. Box 3640, 76021, Karlsruhe, Germany.; Lehn Institute of Functional Materials (LIFM), School of Chemistry, Sun Yat-Sen University (SYSU), Guangzhou, 510275, P. R. China.
Jazyk: angličtina
Zdroj: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2021 Apr 07; Vol. 27 (20), pp. 6295-6307. Date of Electronic Publication: 2021 Mar 03.
DOI: 10.1002/chem.202005207
Abstrakt: The novel diacetylene bridged terphenylic macrocycle 1 is presented and discussed in the context of rotationally restricted "Geländer" oligomers. The 1,4-bis(phenylbuta-1,3-diyn-1-yl) benzene bridge of diacetylene 1 is significantly longer than its terphenyl backbone, forcing the bridge to bend around the central pylon. The synthesis of molecule 1 is based to a large extent on acetylene scaffolding strategies, profiting from orthogonal alkyne protection groups to close both macrocyclic subunits by oxidative acetylene coupling sequentially. The spatial arrangement and the dynamic enantiomerization process of the bicyclic target structure 1 are analyzed. In-depth NMR investigations not only reveal an unexpected spatial arrangement with both oligomer strands bent alongside the backbone, but also display the limited stability of the model compound in the presence of molecular oxygen.
(© 2021 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.)
Databáze: MEDLINE
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