Interactions at the Outer Faces of Calixarenes: 2D Infinite Network Formation with Perfluoroarenes
Chem. Eur. J. 2000, 6, 3495
M. T. Messina, P. Metrangolo, S. Pappalardo, M. F. Parisi, T. Pilati, G. Resnati
Crystal packing of the 2D network obtained starting from a bis-pyridil-calix derivative and 1,4-diiodotetrafluorobenzene. Colours are as follows: black, carbon; sky blue, nitrogen; red, oxygen; purple, iodine; green, fluorine. Dotted lines represent the intramolecular hydrogen bonds; dashed lines represent the intermolecular N···I halogen bonds.
Crystal packing of the 2D network obtained starting from a bis-pyridil-calix derivative and 1,4-diiodotetrafluorobenzene. Colours are as follows: black, carbon; sky blue, nitrogen; red, oxygen; purple, iodine; green, fluorine. Dotted lines represent the intramolecular hydrogen bonds; dashed lines represent the intermolecular N···I halogen bonds.
ABSTRACT
Attractive ð,ð-interactions between two of the four outside cavity faces of 1,3-bis-pyridilcalix[4]arene and both faces of 1,4-diiodotetrafluorobenzene form infinite 1D non-covalent ribbons where the two modules alternate. These ribbons are cross-linked by electron donor-acceptor interactions between picolyl nitrogen atoms of the calixarene in one chain and the iodine atoms of perfluoroarene in another chain forming the 2D supramolecular network. A similar behaviour is also shown by 1,4-dibromotetrafluorobenzene. The ability of electron poor arenes to elicit the exo-receptor potential of calixarene module by connecting their outside faces via ð,ð-interactions may be developed as a new and general binding protocol in calixarene self-assembly processes.