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2019 , Vol. 39 >Issue 12: 3483 - 3489

DOI: https://doi.org/10.6023/cjoc201906006

研究论文

基于柱[5]芳烃的新型双-[1]轮烷的设计与合成

  • 张润淼 ,
  • 王陈威 ,
  • 孙晶 ,
  • 颜朝国 ,
  • 姚勇
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  • a 扬州大学化学化工学院 江苏扬州 225000;
    b 南通大学化学化工学院 江苏南通 226019

收稿日期: 2019-06-06

  修回日期: 2019-07-30

  网络出版日期: 2019-08-07

基金资助

国家自然科学基金（Nos.21801139，21871227）、江苏省自然科学基金（No.BK20180942）、南通大学高层次人才启动基金（No.03083004）、南通大学大型仪器平台开放基金（No.KFJN1814）资助项目.

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Design and Construction of Pillar[5]arene-Based Bis-[1]rotaxane

  • Zhang Runmiao ,
  • Wang Chenwei ,
  • Sun Jing ,
  • Yan Chaoguo ,
  • Yao Yong
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  • a College of Chemistry and Chemistry Engineering, Yangzhou University, Yangzhou, Jiangsu 225000;
    b College of Chemistry and Chemistry Engineering, Nantong University, Nantong, Jiangsu 226019

Received date: 2019-06-06

  Revised date: 2019-07-30

  Online published: 2019-08-07

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21801139, 21871227), the Natural Science Foundation of Jiangsu Province (No. BK20180942), the Natural Science Foundation of Nantong University for High-Level Talent (No. 03083004), and the Large Instruments Open Foudation of Nantong University (No. KFJN1814).

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摘要

以不同长度的亚烷基二胺单元作为柱[5]芳烃边缘侧链的一系列柱[5]单酰胺衍生物，在氯仿中能够形成准[1]轮烷.基于这一中间体准[1]轮烷的合成，通过柱[5]单酰胺衍生物和双水杨醛的缩合反应，成功构建了8个柱芳烃的机械自锁分子（MSMs），即双-[1]轮烷.通过多种方法详细地对新合成的双-[1]轮烷进行了研究，包括1H NMR，13C NMR，2D NOESY NMR和MS分析，发现这类新型MSMs与Cu2＋有较强的识别作用，两者之间以1∶2进行络合.

关键词： 柱[5]芳烃; 双-[1]轮烷; 准[1]轮烷; 机械互锁分子

本文引用格式

张润淼 , 王陈威 , 孙晶 , 颜朝国 , 姚勇 . 基于柱[5]芳烃的新型双-[1]轮烷的设计与合成[J]. 有机化学, 2019 , 39(12) : 3483 -3489 . DOI: 10.6023/cjoc201906006

Abstract

A series of pillar[5]arene monoamide derivatives with different lengths of alkylenediamine unites as the side chains on the pillar[5]arene's rim can form pseudo[1]rotaxanes. Thus, based on the construction of this intermediate of pseudo[1]rotaxane, eight pillar[5]arene-baed mechanically interlocked molecules (MIMs) of bis-[1]rotaxane were successful constructed through condensation reaction of pillar[5]arene monoamide derivative and salicylaldehyde. The newly synthesized bis-[1]rotaxane was investigated in detail by various methods, including 1H NMR, 13C NMR, 2D NOESY NMR and MS analysis. It was found that this kind of MIMs has a strong recognition effect with Cu2+, which complexed by 1:2.

Key words： pillar[5]arene; bis-[1]rotaxane; pseudo[1]rotaxane; mechanically interlocked molecules

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