Scientific article

Rigid Oligonaphthalenediimide Rods as Transmembrane Anion-π Slides

Published inJournal of the American Chemical Society, vol. 128, no. 46, p. 14788-14789
Publication date2006

We report the design, synthesis, and evaluation of rigid oligonaphthalenediimide (O-NDI) rods that are expected to act as transmembrane anion-pi slides. Studies in fluorogenic large unilamellar egg yolk phosphatidylcholine vesicles reveal that rigid O-NDI rods mediate anion-selective transport with a rare halide VI selectivity sequence (Cl- > F- > Br- > I-). This and decreasing activity, selectivity, and halide sequence with increasing positive charge of the rod termini support the occurrence of anion-pi interactions. A strong anomalous mole fraction effect in Cl-/I- mixtures is in agreement with the existence of multiple active sites along the anion-pi slide and multi-anion hopping as a mechanism of transport. The strong inverted NDI quadruple moment found by DFT calculations is in excellent agreement with these results.

Citation (ISO format)
GORTEAU, Virginie et al. Rigid Oligonaphthalenediimide Rods as Transmembrane Anion-π Slides. In: Journal of the American Chemical Society, 2006, vol. 128, n° 46, p. 14788–14789. doi: 10.1021/ja0665747
Updates (1)
ISSN of the journal0002-7863

Technical informations

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