Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 131, Issue 13, Pages 4937-4952Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja809905x
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Funding
- EPSRC
- Fundacao para. a Ciencia e Tecnologia (FCT) [SFRH/BD/29596/2006]
- European Community [PTDC/QUI/68582/2006]
- Royal Society
- SRS Daresbury
- EPSRC [EP/D008417/1] Funding Source: UKRI
- Engineering and Physical Sciences Research Council [EP/D008417/1] Funding Source: researchfish
- Fundação para a Ciência e a Tecnologia [SFRH/BD/29596/2006, PTDC/QUI/68582/2006] Funding Source: FCT
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The design, synthesis, structure, and anion-binding properties of the first indolocarbazole-containing interlocked structure are described. The novel [2]rotaxane molecular structure incorporates a neutral indolocarbazole-containing axle component which is encircled by a tetracationic macrocycle functionalized with an isophthalamide anion recognition motif. H-1 NMR and UV-visible spectroscopies and X-ray crystallography demonstrated the importance of pi-donor-acceptor, CH center dot center dot center dot pi, and electrostatic interactions in the assembly of pseudorotaxanes between the electron-deficient tetracationic macrocycle and a series of pi-electron-rich indolocarbazole derivatives. Subsequent urethane stoppering of one of these complexes afforded a [2]rotaxane, which was shown by H-1 NMR spectroscopic titration experiments to exhibit enhanced chloride and bromide anion recognition compared to its non-interlocked components. Computational molecular dynamics simulations provide further insight into the mechanism and structural nature of the anion recognition process, confirming it to involve cooperative hydrogen-bond donation from both macrocycle and indolocarbazole components of the rotaxane. The observed selectivity of the [2)rotaxane for chloride is interpreted in terms of its unique interlocked binding cavity, defined by the macrocycle isophthalamide and indolocarbazole N-H protons, which is complementary in size and shape to this halide guest.
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