Synthesis of nucleobase-calix[4]arenes via click chemistry and evaluation of their complexation with alkali metal ions and molecular assembly

被引：9

作者：

Liu, Wanbo ^{[1
]}

Minier, Mikael A. ^{[1
]}

Franz, Andreas H. ^{[1
]}

Curtis, Matthew ^{[1
]}

Xue, Liang ^{[1
]}

机构：

[1] Univ Pacific, Dept Chem, Stockton, CA 95211 USA

来源：

SUPRAMOLECULAR CHEMISTRY | 2011年 / 23卷 / 12期

基金：

美国国家科学基金会;

关键词：

calixarene; nucleobase; click chemistry; complexation; molecular assembly; RECOGNITION; CALIXARENES; DERIVATIVES; CA2+; DNA; ASSOCIATION; RULE; NMR;

D O I：

10.1080/10610278.2011.632824

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

In this study, calix[4] arene derivatives (11 14) bearing a single nucleobase (adenine, thymine, cytosine or guanine) were synthesised via click chemistry. The complexation ability of the synthesised derivatives with alkali metal ions was measured using MALDI-TOF mass spectrometry, and their molecular assembly in CDCl3 was determined using H-1 NMR. Calix[4] arene derivatives (11-14) formed 1: 1 complexes with all alkali metal ions and the rank order for the complexation selectivity was Rb+ > Cs+ > K+ congruent to Na+ > Li+. The attachment of nucleobase at the upper rim of calix[4] arene had little effect on its complexation selectivity for alkali metal ions. Thymine-, adenine-and guanine-calix[4] arenes formed self-assembled structures in CDCl3 via base-base interactions. In addition, adenine-calix[4] arene (11) bound to thyminecalix[4]arene (12) to form a discrete species via Hoogsteen hydrogen bonding.

引用

页码：806 / 818

页数：13

共 44 条

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