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Cyclobis(paraquat‐ p ‐phenylene). A Tetracationic Multipurpose Receptor
Author(s) -
Odell Barbara,
Reddington Mark V.,
Slawin Alexandra M. Z.,
Spencer Neil,
Stoddart J. Fraser,
Williams David J.
Publication year - 1988
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198815471
Subject(s) - chemistry , molecule , salt (chemistry) , cyclophane , paraquat , acetonitrile , crystallography , phenylene , ion , bent molecular geometry , benzene , stereochemistry , organic chemistry , polymer
The salt 1ṁ4PF 6 ·3CH 3 CN is a new type of host molecule , which shows similarities to zeolites but is constructed from organic and inorganic ions. The macrocyclic tetracation 1 can be prepared in two steps from bipyridine and 1,4‐bis(bromomethyl)benzene. Calculations and X‐ray crystallography showed the tetracation to have a box‐like structure in which the p ‐phenylene and paraquat units are slightly bent. The PF 6 ⊖ ‐salt of 1 is soluble in organic solvents, the Cl ⊖ salt in water. 1 ·4PF 6 in acetonitrile forms weak inclusion complexes with dimethoxybenzenes, which are stabilized by charge‐transfer interactions. Structural studies of the inclusion complexes show that the electron‐rich guest molecules are located in the cavities ( 2 ); because of the stapling of the alternating tetraction and anion/neutral molecule layers these cavities take the form of channels.