Ryo Morito, Takayuki Kataoka, Kunio Saito, Prof. Dr. Kohtaro Osakada, Dr. Tomohito Ide, Dr. Yoshitaka Tsuchido, Prof. Dr. Hidetoshi Kawai
{"title":"A Water-Soluble Cycloparaphenylene: Supramolecular Receptor with Visible Fluorescence","authors":"Ryo Morito, Takayuki Kataoka, Kunio Saito, Prof. Dr. Kohtaro Osakada, Dr. Tomohito Ide, Dr. Yoshitaka Tsuchido, Prof. Dr. Hidetoshi Kawai","doi":"10.1002/ceur.202400025","DOIUrl":null,"url":null,"abstract":"<p>We report the first synthesis of a water-soluble [9]cycloparaphenylene derivative containing three hydrindacene (1,2,3,5,6,7-hexahydro-<i>s</i>-indacene) units with four carboxylates at the 2,6-positions via a macrocyclic gold complex. This crown-shaped macrocyclic compound exhibits remarkable water solubility, of up to 16 mmol L<sup>−1</sup> (2.6 g/100 mL), as well as strong visible fluorescence in water (λ<sub>em</sub>=447 nm, ϕ<sub>F</sub>=0.64, brightness (ϵ×ϕ<sub>F</sub>)=5.1×10<sup>4</sup>). This molecule effectively encapsulates cationic guest compounds, such as methyl viologen dichloride, as indicated by a change in visible fluorescence.</p>","PeriodicalId":100234,"journal":{"name":"ChemistryEurope","volume":"2 6","pages":""},"PeriodicalIF":0.0000,"publicationDate":"2024-10-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ceur.202400025","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"ChemistryEurope","FirstCategoryId":"1085","ListUrlMain":"https://onlinelibrary.wiley.com/doi/10.1002/ceur.202400025","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 0
Abstract
We report the first synthesis of a water-soluble [9]cycloparaphenylene derivative containing three hydrindacene (1,2,3,5,6,7-hexahydro-s-indacene) units with four carboxylates at the 2,6-positions via a macrocyclic gold complex. This crown-shaped macrocyclic compound exhibits remarkable water solubility, of up to 16 mmol L−1 (2.6 g/100 mL), as well as strong visible fluorescence in water (λem=447 nm, ϕF=0.64, brightness (ϵ×ϕF)=5.1×104). This molecule effectively encapsulates cationic guest compounds, such as methyl viologen dichloride, as indicated by a change in visible fluorescence.