57. “Rigid Oligonaphthalenediimide Rods as Transmembrane Anion-π Slides”
    V. Gorteau, G. Bollot, J. Mareda, A. Perez-Velasco, S. Matile
    J. Am. Chem. Soc. 2006, 128, 14788-14789.

We report the design, synthesis, and evaluation of rigid oligonaphthalenediimide (O-NDI) rods that are expected to act as transmembrane anion−π 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−π interactions. A strong anomalous mole fraction effect in Cl^-/I^- mixtures is in agreement with the existence of multiple active sites along the anion−π 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.

DOI : 10.1021/ja0665747 

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