(Thio)urea resorcinarene cavitands. Complexation and membrane transport of halide anions

被引:71
作者
Boerrigter, H
Grave, L
Nissink, JWM
Chrisstoffels, LAJ
van der Maas, JH
Verboom, W
de Jong, F
Reinhoudt, DN
机构
[1] Univ Twente, Lab Supramol Chem & Technol, SMCT, NL-7500 AE Enschede, Netherlands
[2] Netherlands Energy Res Fdn, ECN, NL-1755 ZG Petten, Netherlands
[3] Univ Utrecht, Dept Analyt Mol Spectrometry, AMS, NL-3508 TB Utrecht, Netherlands
关键词
D O I
10.1021/jo972127l
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Reaction of aminomethylcavitands with iso(thio)cyanates gives (thio)urea-functionalized resorcinarene cavitands, which represent a novel class of neutral anion receptors. The complexation of halide anions has been studied both with infrared and H-1 NMR spectroscopy. The receptors have a small preference for chloride over the other halides; p-fluorophenylthiourea cavitand 8a gives the highest association constant (K-ass = 4.7 x 10(5) M-1 with chloride in CDCl3). A cooperative effect of the ligating (thio)urea moieties is indicated by the lower affinity of the corresponding tris(thio)urea-functionalized cavitands. For the first time facilitated membrane transport of halide anions through supported liquid membranes is achieved.
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页码:4174 / 4180
页数:7
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