By I Prigogine
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Extra info for Advances in Chemical Physics, Vol.2 (Interscience 1958)
2) The hydroquinol ring should be occupied preferentially by the tetracationic cyclophane. (3) The hydroquinol ring should be more easily oxidised than the p-xylyl ring. (4) On oxidation, the x-donating ability of the hydroquinol ring will decrease. (5) The tetracationic cyclophane should now preferentially occupy the p-xylyl residue. (6) Subsequent reduction should regenerate the hydroquinol ring and the bead will return to its starting position, completing the switching cycle. -~,,-- e 14 <+!
The X-ray diffraction analysis of a single crystal of compound 19, although characterized by high disorder of the amide-groups which does not allow to reach a satisfactory R value, clearly indicates a cone confonnation with the OCH3 groups bent inside the cavity ("flattened cone"). The behaviour of the trimethoxy derivatives 19-21 is even more surprising if we compare it with that of p-tert-buty1calixarene hex amide (22). The latter at room 22 temperature is present as a mixture of confonnations, one of which corresponds to the 1,2,3-altemate structure found in the solid state [lOa], but at T > 100°C it is confonnationally mobile .
The functionalization of calixarenes at the "lower rim" (phenolic OH groups) or at the "upper rim" (aromatic nuclei) often produces derivatives with reduced confonnational mobility thus creating new shapes useful for organizing binding or catalytic groups in space. This article will summarize some of our recent efforts to exploit these shapes for the selective recognition of ions and neutral molecules. 2. 1. ENCAPSULATION OF LANTHANIDE IONS 33 p-tert-Butylcalixarene 1 has been treated with NaB in tetrahydrofuran (THF)/N,N-dimethylfonnamide (DMF) followed by the reaction with bromo acetic acid derivatives to produce in high yield the tetraester 4  and the tetramide 5  in the fixed cone confonnation.
Advances in Chemical Physics, Vol.2 (Interscience 1958) by I Prigogine