Mono-functionalized derivatives and revised configurational assignment of amide naphthotubes
Mono-functionalized derivatives and revised configurational assignment of amide naphthotubes
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酰胺萘管的单官能化衍生物和修改后的构型分配
DOI：
10.1039/d0ob00290a
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发表时间：
2020
影响因子：
3.2
通讯作者：
Wei Jiang
中科院分区：
文献类型：
--
作者：
Huan Yao;Xiaoping Wang;Mo Xie;Yu-Mei Wang;Mao Quan;Liu-Pan Yang;Wei Jiang
具有四个羧酸侧链的酰胺类萘甲酸酯已被我们报道用于选择性识别水中的亲水性分子，并已在传感和自组装中得到应用。这些大环化合物在侧链上的修饰将进一步扩大它们的适用性。在此，我们报道了一个炔基和三个羧酸酯基的单官能化酰胺萘甲酸酯的合成。这些萘管显示出与具有四个羧酸酯侧链的酰胺萘管相当不同的结合亲和力。在腔中的炔基团的部分自包含被调用来解释这些差异。此外，在我们的早期出版物中，发现具有四个羧酸根基团的萘并管的顺式和反式构型异构体被错误地分配。这里提供了新任务的进一步证据。这种新的结构分配的影响，在早期的作品中得出的结论进行了讨论。
Amide naphthotubes with four carboxylate sidechains have been reported by us for selectively recognizing hydrophilic molecules in water and they have found applications in sensing and self-assembly. Modification of these macrocycles on the sidechains would further expand their applicability. Herein, we report the synthesis of mono-functionalized amide naphthotubes with one alkyne and three carboxylate groups. These naphthotubes show rather different binding affinities from that of the amide naphthotubes with four carboxylate sidechains. The partial self-inclusion of the alkyne group in the cavity was invoked to explain these differences. In addition, the syn- and anti-configurational isomers of the naphthotubes with four carboxylate groups were found to be assigned incorrectly in our earlier publication. Further evidence is provided here for the new assignment. The implications of this new structural assignment for the conclusions drawn in the earlier works are discussed as well.