Convenient construction of unique bis-[1]rotaxanes based on azobenzene-bridged dipillar[5]arenes

IF 1.7 4区 化学 Q3 CHEMISTRY, MULTIDISCIPLINARY Journal of Inclusion Phenomena and Macrocyclic Chemistry Pub Date : 2021-10-25 DOI:10.1007/s10847-021-01115-0
Dan Li, Ying Han, Jing Sun, Wen-Long Liu, Chao-Guo Yan
{"title":"Convenient construction of unique bis-[1]rotaxanes based on azobenzene-bridged dipillar[5]arenes","authors":"Dan Li,&nbsp;Ying Han,&nbsp;Jing Sun,&nbsp;Wen-Long Liu,&nbsp;Chao-Guo Yan","doi":"10.1007/s10847-021-01115-0","DOIUrl":null,"url":null,"abstract":"<div><p>A series of azobenzene-bridged dipillar[5]arenes were conveniently synthesized by coupling reaction of aminoalkyl-functionalized pillar[5]arenes with azobenzene-4,4’-dioxyacetic acid or azobenzene-4,4’-dioxybutanoic acid in dry chloroform under the combinatorial catalysis of HOBt/EDCl. <sup>1</sup>H NMR, 2D NOESY spectra and single crystal structure clearly indicated that the unique bis-[1]rotaxanes could be formed by threading two diaminoalkylene units into the two cavities of pillar[5]arenes depending on the length of the diaminoalkylene chains. Under light irradiation at 365 nm, the <i>trans</i>-azobenzene unit transferred to <i>cis-</i>configuration, while the basic bis-[1]rotaxane structure was kept unchanged.</p><h3>Graphic abstract</h3>\n <figure><div><div><div><picture><img></picture></div></div></div></figure>\n </div>","PeriodicalId":54324,"journal":{"name":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","volume":"102 3-4","pages":"261 - 270"},"PeriodicalIF":1.7000,"publicationDate":"2021-10-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://link.springer.com/content/pdf/10.1007/s10847-021-01115-0.pdf","citationCount":"4","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://link.springer.com/article/10.1007/s10847-021-01115-0","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 4

Abstract

A series of azobenzene-bridged dipillar[5]arenes were conveniently synthesized by coupling reaction of aminoalkyl-functionalized pillar[5]arenes with azobenzene-4,4’-dioxyacetic acid or azobenzene-4,4’-dioxybutanoic acid in dry chloroform under the combinatorial catalysis of HOBt/EDCl. 1H NMR, 2D NOESY spectra and single crystal structure clearly indicated that the unique bis-[1]rotaxanes could be formed by threading two diaminoalkylene units into the two cavities of pillar[5]arenes depending on the length of the diaminoalkylene chains. Under light irradiation at 365 nm, the trans-azobenzene unit transferred to cis-configuration, while the basic bis-[1]rotaxane structure was kept unchanged.

Graphic abstract

Abstract Image

查看原文
分享 分享
微信好友 朋友圈 QQ好友 复制链接
本刊更多论文
基于偶氮苯桥联双柱[5]芳烃的独特双[1]轮烷的便捷构造
在HOBt/EDCl组合催化下,氨基烷基功能化柱[5]芳烃与偶氮苯-4,4′-二氧乙酸或偶氮苯-4,4′-二氧丁酸在干氯仿中偶联反应,方便地合成了一系列偶氮苯桥接双柱[5]芳烃。1H NMR、2D noesi光谱和单晶结构清楚地表明,根据二氨基亚烯链的长度,将两个二氨基亚烯单元插入柱状[5]芳烃的两个空腔中可以形成独特的双-[1]轮烷。在365 nm光照射下,反式偶氮苯单元转变为顺式构型,而基本的双-[1]轮烷结构保持不变。图形抽象
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
Journal of Inclusion Phenomena and Macrocyclic Chemistry
Journal of Inclusion Phenomena and Macrocyclic Chemistry Agricultural and Biological Sciences-Food Science
CiteScore
4.10
自引率
8.70%
发文量
54
期刊介绍: The Journal of Inclusion Phenomena and Macrocyclic Chemistry is the premier interdisciplinary publication reporting on original research into all aspects of host-guest systems. Examples of specific areas of interest are: the preparation and characterization of new hosts and new host-guest systems, especially those involving macrocyclic ligands; crystallographic, spectroscopic, thermodynamic and theoretical studies; applications in chromatography and inclusion polymerization; enzyme modelling; molecular recognition and catalysis by inclusion compounds; intercalates in biological and non-biological systems, cyclodextrin complexes and their applications in the agriculture, flavoring, food and pharmaceutical industries; synthesis, characterization and applications of zeolites. The journal publishes primarily reports of original research and preliminary communications, provided the latter represent a significant advance in the understanding of inclusion science. Critical reviews dealing with recent advances in the field are a periodic feature of the journal.
期刊最新文献
Meet the new Editor-in-Chief Structural investigations, DFT, anti-oxidant and α-amylase inhibitory activity of metal complexes of benzothiazole based hydrazone Tetrakis(benzoxazine) calix[4]resorcinarenes as hosts for small molecules Nanoporous carbon, its pharmaceutical applications and metal organic frameworks Inclusion of paraoxon, parathion, and methyl parathion into α-cyclodextrin: a GFN2-xTB multi-equilibrium quantum study
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
现在去查看 取消
×
提示
确定
0
微信
客服QQ
Book学术公众号 扫码关注我们
反馈
×
意见反馈
请填写您的意见或建议
请填写您的手机或邮箱
已复制链接
已复制链接
快去分享给好友吧!
我知道了
×
扫码分享
扫码分享
Book学术官方微信
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术
文献互助 智能选刊 最新文献 互助须知 联系我们:info@booksci.cn
Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。
Copyright © 2023 Book学术 All rights reserved.
ghs 京公网安备 11010802042870号 京ICP备2023020795号-1