• 主题
高级搜索  >
历史搜索 清空历史
首页> 外文期刊>Chemistry: A European journal >Template-directed synthesis of multiply mechanically interlocked molecules under thermodynamic control
【24h】

Template-directed synthesis of multiply mechanically interlocked molecules under thermodynamic control

机译：热力学控制下多个机械连锁分子的模板指导合成

获取原文
获取原文并翻译 | 示例
           
页面导航
  • 摘要
  • 著录项
  • 相似文献
  • 相关主题

摘要

The template-directed construction of crown-ether-like macrocycles around secondary dialkylammonium ions (R2NH2+) has been utilized for the expedient (one-pot) and high-yielding synthesis of a diverse range of mechanically interlocked molecules. The clipping together of appropriately designed dialdehyde and diamine compounds around R2NH2+-containing dumbbell-shaped components proceeds through the formation, under thermodynamic control, of imine bonds. The reversible nature of this particular reaction confers the benefits of "error-checking" and "proof-reading", which one usually associates with supramolecular chemistry and strict self-assembly processes, upon these wholly molecular systems. Furthermore, these dynamic covalent syntheses exploit the efficient templating effects that the R2NH2+ ions exert on the macrocyclization of the matched dialdehyde and diamine fragments, resulting not only in rapid rates of reaction, but also affording near-quantitative conversion of starting materials into the desired interlocked products. Once assembled, these "dynamic" interlocked compounds can be "fixed" upon reduction of the reversible imine bonds (by using BH(3)center dot THF) to give kinetically stable species, a procedure that can be performed in the same reaction vessel as the inital thermodynamically controlled assembly. Isolation and purification of the mechanically interlocked products formed by using this protocol is relatively facile, as no column chromatography is required. Herein, we present the synthesis and characterization of 1) a [2]rotaxane, 2) a [3]rotaxane, [3] a branched [4]rotaxane, 4) a bis [2]rotaxane, and 5) a novel cyclic [4]rotaxane, demonstrating, in incrementally more complex systems, the efficacy of this one-pot strategy for the construction of interlocked molecules.
机译：围绕仲二烷基铵离子（R2NH2 +）的冠醚样大环的模板定向构建已用于多种机械互锁分子的简便（一锅法）和高产率合成。在热力学控制下，通过亚胺键的形成，将适当设计的二醛和二胺化合物夹在含R2NH2 +的哑铃状组分上。这种特殊反应的可逆性质赋予了“错误检查”和“校对”的好处，这些好处通常与超分子化学和严格的自组装过程联系在一起。此外，这些动态共价合成利用了R2NH2 +离子对匹配的二醛和二胺片段的大环化作用的有效模板作用，不仅导致了快速的反应速率，而且还提供了从起始原料到所需互锁化合物的近乎定量的转化。产品。一旦组装完成，这些“动态”互锁的化合物就可以通过还原可逆亚胺键而被“固定”（通过使用BH（3）中心点THF），以产生动力学稳定的物质，该过程可在与反应容器相同的反应容器中进行初始热力学控制的组件。由于不需要柱色谱，因此使用此方案形成的机械互锁产物的分离和纯化相对容易。本文中，我们介绍了1）[2]轮烷，2）[3]轮烷，[3]支链[4]轮烷，4）双[2]轮烷和5）新的环状环的合成与表征。 [4]轮烷表明，在越来越复杂的系统中，这种一锅策略用于构建互锁分子的功效。

著录项

相似文献

  • 外文文献
  • 中文文献
  • 专利
获取原文

客服邮箱：kefu@zhangqiaokeyan.com

京公网安备：11010802029741号 ICP备案号：京ICP备15016152号-6 六维联合信息科技 (北京) 有限公司©版权所有

  • 客服微信

  • 服务号