Jiabin Xing, Qihan Lin, Sheng-Yi Zhuang, Gang Wu, Jiangshan Zhang, Hui Wang, Dan-Wei Zhang, Zhan-Ting Li
{"title":"通过释放高能全氟-1-碘烷,利用疏氟效应增强二茂铁的钙[5]炔容器结合力","authors":"Jiabin Xing, Qihan Lin, Sheng-Yi Zhuang, Gang Wu, Jiangshan Zhang, Hui Wang, Dan-Wei Zhang, Zhan-Ting Li","doi":"10.1039/d4qo00672k","DOIUrl":null,"url":null,"abstract":"A hydrogen bonded calix[5]arene cavitand has been designed and prepared, which has a bowl-like cavity of about 0.85 nm width. The binding affinity of the container for ferrocene and its eight derivatives in chloroform is modest. In binary perfluoro-1-iodohexane and chloroform (9:1 v/v), binding constants for the complexes of the seven fluorine-free guests increase by 14.0-144.1 times. In contrast, binding constants for the complexes of two guests that bear a perfluoroheptyl group do not exhibit similar increase. Similar enhancement of binding affinity can also be observed in binary solvents of perfluoro-1-iodobutane or perfluoro-1-iodooctane and chloroform. The results support that perfluoro-1-iodoalkanes molecules in the cavity of the calix[5]arene container function as high-energy ones and their release into the bulk phase is the major driving force for enhanced inclusion of the calix[5]arene container for the fluorine-free guests.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":null,"pages":null},"PeriodicalIF":4.6000,"publicationDate":"2024-06-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Enhancing the binding of calix[5]arene containers for ferrocenes by fluorophobic effect through the release of high-energy perfluoro-1-iodoalkanes\",\"authors\":\"Jiabin Xing, Qihan Lin, Sheng-Yi Zhuang, Gang Wu, Jiangshan Zhang, Hui Wang, Dan-Wei Zhang, Zhan-Ting Li\",\"doi\":\"10.1039/d4qo00672k\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"A hydrogen bonded calix[5]arene cavitand has been designed and prepared, which has a bowl-like cavity of about 0.85 nm width. The binding affinity of the container for ferrocene and its eight derivatives in chloroform is modest. In binary perfluoro-1-iodohexane and chloroform (9:1 v/v), binding constants for the complexes of the seven fluorine-free guests increase by 14.0-144.1 times. In contrast, binding constants for the complexes of two guests that bear a perfluoroheptyl group do not exhibit similar increase. Similar enhancement of binding affinity can also be observed in binary solvents of perfluoro-1-iodobutane or perfluoro-1-iodooctane and chloroform. The results support that perfluoro-1-iodoalkanes molecules in the cavity of the calix[5]arene container function as high-energy ones and their release into the bulk phase is the major driving force for enhanced inclusion of the calix[5]arene container for the fluorine-free guests.\",\"PeriodicalId\":97,\"journal\":{\"name\":\"Organic Chemistry Frontiers\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":4.6000,\"publicationDate\":\"2024-06-12\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic Chemistry Frontiers\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1039/d4qo00672k\",\"RegionNum\":1,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Chemistry Frontiers","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1039/d4qo00672k","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Enhancing the binding of calix[5]arene containers for ferrocenes by fluorophobic effect through the release of high-energy perfluoro-1-iodoalkanes
A hydrogen bonded calix[5]arene cavitand has been designed and prepared, which has a bowl-like cavity of about 0.85 nm width. The binding affinity of the container for ferrocene and its eight derivatives in chloroform is modest. In binary perfluoro-1-iodohexane and chloroform (9:1 v/v), binding constants for the complexes of the seven fluorine-free guests increase by 14.0-144.1 times. In contrast, binding constants for the complexes of two guests that bear a perfluoroheptyl group do not exhibit similar increase. Similar enhancement of binding affinity can also be observed in binary solvents of perfluoro-1-iodobutane or perfluoro-1-iodooctane and chloroform. The results support that perfluoro-1-iodoalkanes molecules in the cavity of the calix[5]arene container function as high-energy ones and their release into the bulk phase is the major driving force for enhanced inclusion of the calix[5]arene container for the fluorine-free guests.
期刊介绍:
Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.