Jump to main content
Jump to site search

Issue 4, 2012
Previous Article Next Article

Enantioselective self-sorting on planar, π-acidic surfaces of chiral anion-π transporters

Author affiliations

Abstract

Self-sorting at interfaces is one of the big challenges we face to prepare the functional organic materials of the future. As a first and decisive step to self-sorting into π-stacks or bundles, we here elaborate self-sorting of π-dimers in solution. Design, synthesis and study of planar naphthalenediimides (NDIs) with one shielded and one free chiral π-surface to direct self-assembly into dimers are described. Stereoisomers are isolated by chiral, preparative HPLC and characterized by X-ray crystallography. NMR studies show that racemates with almost planar, nearly identical π-surfaces prefer uniform self-sorting into homodimers at large differences in π-acidity and alternate self-sorting into heterodimers at small differences in π-acidity. In contrast, enantiomers self-sort “narcissistically” into heterodimers and diastereomers show moderate preference for homodimers. Whereas the lessons learned from dimerization are directly applicable to self-sorting of π-stacks on surfaces, anion transport in lipid bilayers is shown to require a more subtle, somewhat inverse interpretation, with diastereomeric transporters differing dramatically in activity but the least visible supramolecule being confirmed as the best performer.

Graphical abstract: Enantioselective self-sorting on planar, π-acidic surfaces of chiral anion-π transporters

Back to tab navigation

Supplementary files

Publication details

The article was received on 03 Dec 2011, accepted on 20 Dec 2011 and first published on 11 Jan 2012


Article type: Edge Article
DOI: 10.1039/C2SC01013E
Citation: Chem. Sci., 2012,3, 1121-1127
  •   Request permissions

    Enantioselective self-sorting on planar, π-acidic surfaces of chiral anion-π transporters

    N. Lin, A. Vargas Jentzsch, L. Guénée, Jörg-M. Neudörfl, S. Aziz, A. Berkessel, E. Orentas, N. Sakai and S. Matile, Chem. Sci., 2012, 3, 1121
    DOI: 10.1039/C2SC01013E

Search articles by author

Spotlight

Advertisements