Rigid oligonaphthalenediimide rods as transmembrane anion-π slides

被引：260

作者：

Gorteau, Virginie ^{[1
]}

Bollot, Guillaume ^{[1
]}

Mareda, Jiri ^{[1
]}

Perez-Velasco, Alejandro ^{[1
]}

Matile, Stefan ^{[1
]}

机构：

[1] Univ Geneva, Dept Organ Chem, CH-1211 Geneva, Switzerland

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2006年 / 128卷 / 46期

关键词：

D O I：

10.1021/ja0665747

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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. Copyright © 2006 American Chemical Society.

引用

页码：14788 / 14789

页数：2

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