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Issue 26, 2018
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Molecular dynamic staircases: all-carbon axial chiral “Geländer” structures

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Abstract

Herein, the syntheses of two tightly packed all-carbon “Geländer” molecules with axial chirality are described. Motivated by our previous results, we further reduced the bridge length by excluding the heteroatoms. The absolute configuration was determined by comparison of the measured and calculated circular dichroism (CD) spectra and the thermodynamic stability was determined by dynamic high-performance liquid chromatography (HPLC) and CD analysis. The cyclophanes were fully characterized by CD measurements, X-ray diffraction (XRD) analysis, NMR, UV-Vis and high resolution mass spectrometry (HRMS). Our novel all-carbon macrocycle is the most stable Geländer system reported so far.

Graphical abstract: Molecular dynamic staircases: all-carbon axial chiral “Geländer” structures

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Supplementary files

Article information


Submitted
13 Apr 2018
Accepted
31 May 2018
First published
05 Jun 2018

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2018,9, 5758-5766
Article type
Edge Article

Molecular dynamic staircases: all-carbon axial chiral “Geländer” structures

R. Mannancherry, M. Rickhaus, D. Häussinger, A. Prescimone and M. Mayor, Chem. Sci., 2018, 9, 5758
DOI: 10.1039/C8SC01707G

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