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

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Neudörfl, Jörg-M.
Aziz, Sarwar
Berkessel, Albrecht
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Published in Chemical Science. 2012, vol. 3, no. 4, p. 1121-1127
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.
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Other version: http://xlink.rsc.org/?DOI=c2sc01013e
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LIN, Nai-Di et al. Enantioselective self-sorting on planar, π-acidic surfaces of chiral anion-π transporters. In: Chemical Science, 2012, vol. 3, n° 4, p. 1121-1127. https://archive-ouverte.unige.ch/unige:18776

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Deposited on : 2012-03-09

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