Recognition of caffeine in aqueous solutions

被引：44

作者：

Fiammengo, R ^{[1
]}

Crego-Calama, M ^{[1
]}

Timmerman, P ^{[1
]}

Reinhoudt, DN ^{[1
]}

机构：

[1] Univ Twente, Lab Supramol Chem & Technol, MESA Res Inst, NL-7500 AE Enschede, Netherlands

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2003年 / 9卷 / 03期

关键词：

caffeine; noncovalent interactions; porphyrinoids; sensors; water chemistry;

D O I：

10.1002/chem.200390088

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Binding of caffeine in aqueous solutions has been achieved for the first time by using water-soluble, tetracationic peptide-porphyrin conjugates Zn-1 as the receptor molecules. The association constant for caffeine with receptor Zn-1 is in some cases as high as 6000 m(-1), only 5-6 times lower than the highest binding constant reported for an artificial caffeine receptor in low polarity aprotic solvents. The binding mechanism has been studied by a combination of experimental techniques such as UV-visible and NMR spectroscopy and microcalorimetry. Recognition of caffeine involves both stacking with the porphyrin ring and metal coordination. Subtle variations of the receptor structure affect the complexation. Receptors Zn-1 have also been investigated for the recognition of molecules structurally related to caffeine, for example, 1-methylimidazole. Selectivity towards oxopurine derivatives (caffeine and theophylline) have been found.

引用

页码：784 / 792

页数：9

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