Nondegenerate pi-donor/pi-acceptor [2]catenanes containing proton-ionizable 1H-1,2,4-triazole subunits: synthesis and spontaneous resolution |
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Authors: | Alcalde Ermitas Pérez-García Lluïsa Ramos Susana Stoddart J Fraser White Andrew J P Williams David J |
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Institution: | Laboratori de Química Orgànica, Facultat de Farmàcia and Institut de Nanociència i Nanotecnologia, Universitat de Barcelona, Avda. Joan XXIII s/n, 08028-Barcelona, Spain. |
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Abstract: | Chirality can hold the key to inducing directionality of motion in components of molecular devices. With this idea in mind, we describe here 1) the template-directed synthesis of two 2]catenanes wherein cyclobis(paraquat-p-phenylene) is interlocked with polyether macrocycles containing, in addition to one 3,5-bis(oxymethylene)-1H-1,2,4-triazole unit, either one 1,4-dioxybenzene or one 1,5-dioxynaphthalene ring system. We also report 2) the full characterization of both 2]catenanes by fast atom bombardment mass spectrometry (FABMS), X-ray crystallography, and dynamic (1)H NMR spectroscopy. We reveal 3) the fact that the 2]catenanes not only exist, both in the solution-state and in the solid-state, as strictly one of the two possible translational isomers, but that they also exhibit spontaneous resolution on crystallization leading to formation of homochiral crystals, as indicated by X-ray crystallography and circular dichroism (CD) experiments. Finally, we comment 4) on the chances of switching these catenanes chemically. |
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Keywords: | catenanes self‐assembly spontaneous resolution supramolecular chemistry template synthesis |
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