Synthesis, X-ray Structure, and Anion-Binding Properties of a Cryptand-Like Hybrid Calixpyrrole

The novel cryptand in/out-3, containing two tripyrrolemethane units bridged by three 1,3- diisopropylidenbenzene arms, was readily synthesized by a convergent three-step synthesis. It binds fluoride by inclusion with excellent selectivity with respect to a number of other tested anions. The structur...

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Veröffentlicht in:	Journal of organic chemistry 2010-09, Vol.75 (18), p.6263-6266
Hauptverfasser:	Cafeo, Grazia, Colquhoun, Howard M, Cuzzola, Angela, Gattuso, Mario, Kohnke, Franz H, Valenti, Luca, White, Andrew J. P
Format:	Artikel
Sprache:	eng
Schlagworte:	Anions - chemistry Binding Sites Calixarenes - chemical synthesis Calixarenes - chemistry Chemistry Crystallography, X-Ray Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings Models, Molecular Molecular Structure Organic chemistry Preparations and properties Pyrroles - chemical synthesis Pyrroles - chemistry Stereoisomerism
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Beschreibung
Zusammenfassung:	The novel cryptand in/out-3, containing two tripyrrolemethane units bridged by three 1,3- diisopropylidenbenzene arms, was readily synthesized by a convergent three-step synthesis. It binds fluoride by inclusion with excellent selectivity with respect to a number of other tested anions. The structure of the free receptor and that of its fluoride complex were investigated in solution by NMR spectroscopy. The solid-state X-ray structure of the free cryptand 3 was also determined.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo1010262