{"title":"Encapsulation of Cofacial Diarylacetylene Dimers Using [","authors":"2]Daisy Chain Rotaxane Strategy","doi":"10.3987/com-23-14921","DOIUrl":null,"url":null,"abstract":"<span>[</span><span>c</span><span>2]Daisy chain rotaxanes are mechanically interlocked molecules that can cofacially assemble two </span><span>π</span><span>-conjugated molecules. In this study, we employed a rotaxane architecture to encapsulate diarylacetylene dimers modified with an electron-withdrawing or electron-donating substituent in two permethylated </span><span>α</span><span>-cyclodextrins. Solvent- and concentration-dependent </span><span>1</span><span>H nuclear magnetic resonance measurements indicated the selective formation of the cofacial dimers. These dimers were mechanically interlocked by condensation with 4-{2-[2-(2-hydroxyethoxy)ethoxy]ethoxy}-3,5-dimethylaniline to obtain the corresponding [</span><span>c</span><span>2]daisy chain rotaxanes (up to 68% yield). UV-visible absorption and fluorescence spectra revealed that the diarylacetylene substituents modulated the optical properties of the rotaxanes. </span>","PeriodicalId":13166,"journal":{"name":"Heterocycles","volume":null,"pages":null},"PeriodicalIF":0.8000,"publicationDate":"2023-11-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Heterocycles","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.3987/com-23-14921","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
[c2]Daisy chain rotaxanes are mechanically interlocked molecules that can cofacially assemble two π-conjugated molecules. In this study, we employed a rotaxane architecture to encapsulate diarylacetylene dimers modified with an electron-withdrawing or electron-donating substituent in two permethylated α-cyclodextrins. Solvent- and concentration-dependent 1H nuclear magnetic resonance measurements indicated the selective formation of the cofacial dimers. These dimers were mechanically interlocked by condensation with 4-{2-[2-(2-hydroxyethoxy)ethoxy]ethoxy}-3,5-dimethylaniline to obtain the corresponding [c2]daisy chain rotaxanes (up to 68% yield). UV-visible absorption and fluorescence spectra revealed that the diarylacetylene substituents modulated the optical properties of the rotaxanes.
期刊介绍：
Since its inception in 1973 HETEROCYCLES has provided a platform for the rapid exchange of research in the areas of organic, pharmaceutical, analytical, and medicinal chemistry of heterocyclic compounds in addition to communications, papers, reviews, a special section of the journal presents newly-discovered natural products whose structure has recently been established.
Another section is devoted to the total synthesis of previously documented natural products with heterocyclic ring systems.
Due to the fact that the journal is able to publish articles within two months of receipt of the manuscripts, researchers in this field can obtain up-to-date information on heterocyclic research by reading Heterocycles regularly.
Audience: Organic and Physical Organic Chemists, Biochemists, Pharmacologists and Scientists studying heterocyclic compounds
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