Abstract
An approach to the supramolecular syntheses of discrete multicomponent aggregates of noncovalently bound molecules, i.e., supermolecules, is described. This approach involved the careful analysis of X-ray crystal structures so as to permit a gradual increase in superstructural complexity. Many elaborate supermolecules were synthesized noncovalently from dialkylammonium-containing cations and crown ethers, following the initial observation that the dibenzylammonium ion threads through dibenzo[24]crown-8 to generate a singly stranded, singly encircled [2]pseudorotaxane, principally as a result of \( \left[{\mathrm{N}}^{+}\mathrm{H}\cdots \mathrm{O}\right] \) and \( \left[\mathrm{C}\mathrm{H}\cdots \mathrm{O}\right] \) hydrogen bond formation. The scope of the fundamental recognition motif obtained from this initial observation was then broadened, through the use of thread-like ions with multiple dialkylammonium centers and/or larger crown ethers, so that multiply stranded and/or multiply encircled pseudorotaxanes could be prepared. Cations bearing both dialkylammonium and crown ether recognition sites were also used for the noncovalent synthesis of a discrete daisy chain supermacrocycle and the basic recognition motif was combined with other motifs for the production of a wide range of novel superarchitectures. As a greater understanding of the noncovalent interactions governing the self-assembly of the complex superarchitectures was acquired, new protocols for the noncovalent syntheses of doubly docked pseudorotaxanes and interwoven supramolecular bundles, including a supramolecular analogue of the photosynthetic special pair, were developed. The discovery that anions can play a prominent role in the solid-state self-assembly of some of the supermolecules was a valuable spinoff of the research.
Structural Chemistry 1999, 10(3):243–259.
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Fyfe, M.C.T., Stoddart, J.F., Williams, D.J. (2015). X-ray Crystallographic Studies on the Noncovalent Syntheses of Supermolecules. In: Hargittai, I., Hargittai, B. (eds) Science of Crystal Structures. Springer, Cham. https://doi.org/10.1007/978-3-319-19827-9_23
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