Issue 4, 2012

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

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

Supplementary files

Article information

Article type
Edge Article
Submitted
03 Dec 2011
Accepted
20 Dec 2011
First published
11 Jan 2012

Chem. Sci., 2012,3, 1121-1127

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

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