Issue 26, 2018

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


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

Supplementary files

Article information

Article type
Edge Article
13 Apr 2018
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
Creative Commons BY license

Chem. Sci., 2018,9, 5758-5766

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

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

Read more about how to correctly acknowledge RSC content.

Social activity