Turning on anion and betaine hosting by a small structural change of a biomimetic cavity: a case study

IF 2.1 4区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY Supramolecular Chemistry Pub Date : 2021-07-03 DOI:10.1080/10610278.2021.2011890

G. De Leener, D. Over, O. Reinaud, I. Jabin

引用次数: 0

Abstract

ABSTRACT This study explores the impact of a small structural modification on a biomimetic receptor. The hosting structure is a calix[6]arene capped by a tetraaza core. Two receptors are compared: one (1) presents three anisole units while the other (2) has three phenols. The latter was obtained with an excellent yield by selective demethylation thanks to a supramolecular strategy. Complexation studies showed that [2.H]+ displays strong affinities for Cl−, NO3 −, HSO4 −, whereas [1.H]+ is non-responsive. The anions are embedded at the level of the small rim, hydrogen-bonded to the protonated cap and the phenol groups. Ternary complexes are obtained in the presence of ammoniums. Finally, [2.H]+ shows high affinity for small zwitterions presenting a carboxylate and an ammonium groups separated by one or two carbon atom(s), not three, due to multi-point recognition. These results open routes to the design of new receptors for a variety of anionic and zwitterionic guests.

查看原文

微信好友朋友圈 QQ好友复制链接

本刊更多论文

通过仿生腔的微小结构变化开启阴离子和甜菜碱寄主:一个案例研究

本研究探讨了一个小的结构修饰对仿生受体的影响。载体结构为杯[6]芳烃，由四氮核包裹。比较两种受体:一种(1)有三个苯甲醚单元，而另一种(2)有三个酚。后者通过选择性去甲基化获得了极好的产率，这要归功于超分子策略。络合研究表明，[2.H]+对Cl−、NO3−、HSO4−具有较强的亲和性，而[1.H]+对Cl−、NO3−、HSO4−没有反应。阴离子嵌入在小边缘的水平，氢键与质子化的帽和苯酚基团相连。三元配合物在氨的存在下得到。最后，由于多点识别，[2.H]+对小的两性离子表现出很高的亲和力，表现出由一个或两个碳原子(而不是三个)分开的羧酸盐和铵基。这些结果为设计各种阴离子和两性离子客体的新受体开辟了道路。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

求助全文

约1分钟内获得全文去求助

来源期刊

Supramolecular Chemistry 化学-化学综合

CiteScore

3.60

自引率

3.00%

发文量

审稿时长

2.7 months

期刊介绍： Supramolecular Chemistry welcomes manuscripts from the fields and sub-disciplines related to supramolecular chemistry and non-covalent interactions. From host-guest chemistry, self-assembly and systems chemistry, through materials chemistry and biochemical systems, we interpret supramolecular chemistry in the broadest possible sense. Interdisciplinary manuscripts are particularly encouraged. Manuscript types include: high priority communications; full papers; reviews, and; Methods papers, techniques tutorials highlighting procedures and technologies that are important to the field. We aim to publish papers in a timely fashion and as soon as a paper has been accepted and typeset it will be published in electronic form on the Latest articles section of the website. The two most important review criteria are that the paper presents high-quality work that fits generally into the broad spectrum of activities in the supramolecular chemistry field. Under normal circumstances, Supramolecular Chemistry does not consider manuscripts that would be more suitable in a highly specialized journal. This includes, but is not limited to, those based mostly or exclusively on topics such as solid state/X-ray structures, computational chemistry, or electrochemistry. . The two most important review criteria are that the paper presents high-quality work that fits generally into the broad spectrum of activities in the supramolecular chemistry field.