Ilaria Quaratesi, Paolo Della Sala, Clotilde Capacchione, Carmen Talotta, S. Geremia, N. Hickey, Rocco Gliubizzi, Immacolata Bruno, C. Sgarlata, R. Migliore, C. Gaeta, P. Neri
{"title":"β-环糊精对水中双酚S异构体的选择性识别","authors":"Ilaria Quaratesi, Paolo Della Sala, Clotilde Capacchione, Carmen Talotta, S. Geremia, N. Hickey, Rocco Gliubizzi, Immacolata Bruno, C. Sgarlata, R. Migliore, C. Gaeta, P. Neri","doi":"10.1080/10610278.2021.1991925","DOIUrl":null,"url":null,"abstract":"ABSTRACT The two isomers 4,4´-dihydroxydiphenyl sulphone and 2,4´-dihydroxydiphenyl sulphone (bisphenol S, BPS) form inclusion complexes with β-CD in solution, in the gas phase, and in the solid state. The complexes 4,4´-BPS@β-CD and 2,4´-BPS@β-CD were studied in solution by 1D and 2D NMR experiments. Calorimetric investigation by ITC evidenced that the β-CD host shows a greater affinity for 4,4´-BPS, with a 4,4´-BPS/2,4´-BPS selectivity ratio of 6.3. In the gas phase, CID MS experiments indicate that 4,4´-BPS has a higher kinetic barrier to escape from the β-CD cavity than the isomeric 2,4´-BPS. In the solid state, the 4,4´-BPS@β-CD and 2,4´-BPS@β-CD complexes form head-to-head dimers constituted by two β-CD macrocycles, with each β-CD hosting one BPS guest. The dimers of β-CD are sealed by H-bonding interactions involving exclusively the secondary OH groups. Finally, the formation of inclusion complexes between 4,4´-BPS or 2,4´-BPS and β-CD was also followed by FT-IR, DSC, and TGA analysis. Graphical abstract","PeriodicalId":22084,"journal":{"name":"Supramolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.1000,"publicationDate":"2021-06-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"1","resultStr":"{\"title\":\"Selective recognition of bisphenol S isomers in water by β-cyclodextrin\",\"authors\":\"Ilaria Quaratesi, Paolo Della Sala, Clotilde Capacchione, Carmen Talotta, S. Geremia, N. Hickey, Rocco Gliubizzi, Immacolata Bruno, C. Sgarlata, R. Migliore, C. Gaeta, P. Neri\",\"doi\":\"10.1080/10610278.2021.1991925\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"ABSTRACT The two isomers 4,4´-dihydroxydiphenyl sulphone and 2,4´-dihydroxydiphenyl sulphone (bisphenol S, BPS) form inclusion complexes with β-CD in solution, in the gas phase, and in the solid state. The complexes 4,4´-BPS@β-CD and 2,4´-BPS@β-CD were studied in solution by 1D and 2D NMR experiments. Calorimetric investigation by ITC evidenced that the β-CD host shows a greater affinity for 4,4´-BPS, with a 4,4´-BPS/2,4´-BPS selectivity ratio of 6.3. In the gas phase, CID MS experiments indicate that 4,4´-BPS has a higher kinetic barrier to escape from the β-CD cavity than the isomeric 2,4´-BPS. In the solid state, the 4,4´-BPS@β-CD and 2,4´-BPS@β-CD complexes form head-to-head dimers constituted by two β-CD macrocycles, with each β-CD hosting one BPS guest. The dimers of β-CD are sealed by H-bonding interactions involving exclusively the secondary OH groups. Finally, the formation of inclusion complexes between 4,4´-BPS or 2,4´-BPS and β-CD was also followed by FT-IR, DSC, and TGA analysis. Graphical abstract\",\"PeriodicalId\":22084,\"journal\":{\"name\":\"Supramolecular Chemistry\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":2.1000,\"publicationDate\":\"2021-06-03\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"1\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Supramolecular Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1080/10610278.2021.1991925\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q3\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Supramolecular Chemistry","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1080/10610278.2021.1991925","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
Selective recognition of bisphenol S isomers in water by β-cyclodextrin
ABSTRACT The two isomers 4,4´-dihydroxydiphenyl sulphone and 2,4´-dihydroxydiphenyl sulphone (bisphenol S, BPS) form inclusion complexes with β-CD in solution, in the gas phase, and in the solid state. The complexes 4,4´-BPS@β-CD and 2,4´-BPS@β-CD were studied in solution by 1D and 2D NMR experiments. Calorimetric investigation by ITC evidenced that the β-CD host shows a greater affinity for 4,4´-BPS, with a 4,4´-BPS/2,4´-BPS selectivity ratio of 6.3. In the gas phase, CID MS experiments indicate that 4,4´-BPS has a higher kinetic barrier to escape from the β-CD cavity than the isomeric 2,4´-BPS. In the solid state, the 4,4´-BPS@β-CD and 2,4´-BPS@β-CD complexes form head-to-head dimers constituted by two β-CD macrocycles, with each β-CD hosting one BPS guest. The dimers of β-CD are sealed by H-bonding interactions involving exclusively the secondary OH groups. Finally, the formation of inclusion complexes between 4,4´-BPS or 2,4´-BPS and β-CD was also followed by FT-IR, DSC, and TGA analysis. Graphical abstract
期刊介绍:
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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.