Journal
NATURE CHEMISTRY
Volume 5, Issue 8, Pages 704-710Publisher
NATURE PUBLISHING GROUP
DOI: 10.1038/NCHEM.1668
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Funding
- National Science Foundation [NSF/CHE-0844441]
- Department of Energy [NSF/CHE-0822838]
- US Department of Energy, Office of Science, Office of Basic Energy Sciences [DE-AC02-06CH11357]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [0844441] Funding Source: National Science Foundation
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Since the discovery of crown ethers, macrocycles have been recognized as powerful platforms for supramolecular chemistry. Although their numbers and variations are now legion, macrocycles that are simple to make using high-yielding reactions in one pot and on the multigram scale are rare. Here we present such a discovery obtained during the creation of a C-5-symmetric cyanostilbene 'campestarene' macrocycle, cyanostar, that employs Knoevenagel condensations in the preparation of its cyanostilbene repeat unit. In the solid state, cyanostars form pi-stacked dimers constituted of chiral P and M enantiomers. The electropositive central cavity stabilizes anions with CH hydrogen-bonding units that are activated by electron-withdrawing cyano groups. In solution, the cyanostar shows high-affinity binding as 2:1 sandwich complexes, log beta(2) approximate to 12 and Delta G approximate to -70 kJ mol(-1), of large anions (BF4-, ClO4- and PF6-) usually considered weakly coordinating. The cyanostar's size preference allowed formation of an unprecedented [3]rotaxane templated around a dialkylphosphate.
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