Orientation of the α-CD component of [2]rotaxanes affects their specific molecular recognition behaviour,Organic Chemistry Frontiers

当前位置： X-MOL 学术 › Org. Chem. Front. › 论文详情

Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)

Orientation of the α-CD component of [2]rotaxanes affects their specific molecular recognition behaviour
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2020-11-26 , DOI: 10.1039/d0qo01337d
Takuya Iwamoto _{1,

2,

3,

4,

5} , Shinobu Miyagawa _{1,

2,

3,

4,

5} , Masaya Naito _{1,

2,

3,

4,

5} , Yuji Tokunaga _{1,

2,

3,

4,

5}

Affiliation

In this study we synthesized a pair of orientationally isomeric [2]rotaxanes (1 and 2) featuring an α-cyclodextrin (α-CD) as the macrocyclic component and phenylurea and 2-hydroxybenzophenone moieties as stoppers of the axle-like component. The presence of the α-CD component enhanced the anion recognition ability of the urea unit in isomer 1, with the OH groups on the wide rim of α-CD undergoing hydrogen bonding with the anions. The association constant for the interaction between 1 and the acetate (AcO⁻) anion was more than four times that of the corresponding non-interlocked dumbbell-shaped molecule and the AcO⁻ anion. The other isomer 2, in which the wide rim of the α-CD component faced the 2-hydroxybenzophenone unit, was preferentially deprotonated by the AcO⁻ anion to give the phenoxide anion, which was stabilized through noncovalent interactions with the OH groups on the wide rim of the α-CD unit in an organic solvent; in contrast, the AcO⁻ anion did not deprotonate the corresponding non-interlocked dumbbell-shaped molecule.

中文翻译：

[2]轮烷的α-CD成分的取向影响其特定的分子识别行为

在这项研究中，我们合成了一对定向异构的[2]轮烷（1和2），其特征在于α-环糊精（α-CD）作为大环成分，苯基脲和2-羟基二苯甲酮部分作为轴状成分的塞子。α-CD组分的存在增强了异构体1中尿素单元的阴离子识别能力，α-CD宽边上的OH基团与阴离子发生氢键结合。对之间的相互作用的缔合常数1和醋酸（ACO ^{- ）}阴离子是相应的非互锁哑铃状分子和ACO的四倍以上^-的阴离子。其他异构体2，其中，所述α-CD分量的宽边沿面对的2-羟基二苯甲酮单元，由ACO被优先去质子化^-阴离子，得到酚盐阴离子，其是通过与OH基团的非共价相互作用的α的宽边沿稳定-CD单元在有机溶剂中；与此相反，ACO ^-阴离子没有去质子化相应的非互锁哑铃形分子。

更新日期：2020-12-17

点击分享查看原文

点击收藏

阅读更多本刊最新论文本刊介绍/投稿指南11