Hydrophobic concave surfaces and cavities by combination of calix[4]arenes and resorcin[4]arenes

Peter Timmerman, Klaas G.A. Nierop, Erik A. Brinks, Willem Verboom, Frank C.J.M. van Veggel, Willem P. van Hoorn, David N. Reinhoudt

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A general approach to the family of completely spirocyclopropanated macrocyclic polydiacetylenes, that is, cyclic dehydrooligomers of 1,1-diethynylcyclopropane 4, is reported. The characterized examples of these 'exploding' [n]rotanes are for n = 5, 6, 7, 8, 9, 10, and 12. X-ray crystal structure analyses for the hydrocarbons with n = 5, 6, 7, and 8 disclose a strong electronic interaction between the cyclopropane and the acetylene units leading to a significant shortening of the distal and lengthening of the proximal cyclopropane bonds. While the five-sided compound 18 can occur as a planar or envelope-shaped molecule, depending on the solvent from which crystals are grown, the six- (19), seven- (20), and eight-sided (21) molecules all have chair conformations. While the butadiyne units in 18 and 19 are bent slightly outwards, those in the seven- and eight-sided molecules 20 and 21, respectively, are bent distinctly inward. All these compounds are extremely high-energy molecules: when struck with a spatula or a pestle, they go off with a puff to yield black soot.
Original languageEnglish
Pages (from-to)132-143
Number of pages8
JournalChemistry : a European journal
Issue number2
Publication statusPublished - 1995


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