Jump to main content
Jump to site search

Issue 2, 2016
Previous Article Next Article

Readily prepared inclusion forming chiral calixsalens

Author affiliations


Calixsalens, chiral triangular hexaimines are readily synthesized by [3 + 3] cyclocondensation of trans-(R,R)-1,2-diaminocyclohexane with 2-hydroxyisophthalaldehyde derivatives. The usually rigid calixsalen ring is able to invert its conformation as a consequence of steric repulsion between bulky substituents at the C5 positions of the aromatic rings. The steric and electronic nature of the substituents does not affect only the conformation of the macrocycle. Small polar substituents enforce dimeric self-association to form an apohost where each of the monomers simultaneously serves as the host and the guest of its partner. Non-associating calixsalens form assemblies in which two symmetry-related molecules are arranged in a head-to-head fashion to form a capsule, or unimolecular cages that are able to entrap solvent molecules in their intrinsic voids.

Graphical abstract: Readily prepared inclusion forming chiral calixsalens

Back to tab navigation

Supplementary files

Publication details

The article was received on 08 Oct 2015, accepted on 30 Oct 2015 and first published on 02 Nov 2015

Article type: Paper
DOI: 10.1039/C5OB02090E
Author version
Download author version (PDF)
Citation: Org. Biomol. Chem., 2016,14, 669-673
  •   Request permissions

    Readily prepared inclusion forming chiral calixsalens

    A. Janiak, M. Petryk, L. J. Barbour and M. Kwit, Org. Biomol. Chem., 2016, 14, 669
    DOI: 10.1039/C5OB02090E

Search articles by author