Resorcinarenes are hexameric capsules in solution

被引:121
作者
Evan-Salem, Tamar
Baruch, Inbal
Avram, Liat
Cohen, Yoram
Palmer, Liam C.
Rebek, Julius, Jr.
机构
[1] Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA
[2] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
[3] Tel Aviv Univ, Sackler Fac Exact Sci, IL-69978 Tel Aviv, Israel
关键词
diffusion spectroscopy; encapsulation; self-assembly; SYNTHETIC POLYHYDROXY MACROCYCLE; HYDROGEN-BONDING INTERACTION; HOST-GUEST COMPLEXATION; MOLECULAR RECOGNITION; DIFFUSION NMR; ALDEHYDE CYCLOTETRAMER; POLAR COMPOUNDS; BINDING; SPECTROSCOPY; SELECTIVITY;
D O I
10.1073/pnas.0604757103
中图分类号
O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];
学科分类号
07 ; 0710 ; 09 ;
摘要
The host-guest complexes of resorcin[4]arenes with small molecules in organic solutions are examined using modern NMR spectroscopic methods. The complexation of glutaric acid and beta-methyl D-glucopyranoside in chloroform were investigated through 2D COSY, 2D NOESY, 1D NOE, and diffusion-ordered NMR spectroscopy (DOSY) techniques. These methods indicate that the complex is a self-assembled capsule composed of six resorcinarenes that surround six guest molecules of glutaric acid or three molecules of beta-methyl D-glucopyranoside inside. The multiplicity of guest proton signals shows that the capsule provides an asymmetric magnetic environment that persists on the H-1 NMR time scale. The encapsulation of these guests and common solvents suggests that the phenomenon of reversible encapsulation in chemistry may be a century old.
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页码:12296 / 12300
页数:5
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