{"title":"基于香豆素的比色化学传感器的硫代羰基类似物的合成:改变Fe对Hg(ii)和Cu(ii)离子的选择性","authors":"Stiaan Schoeman, Neliswa Mama and Lisa Myburgh","doi":"10.1039/D4NJ05130K","DOIUrl":null,"url":null,"abstract":"<p >Lawesson's reagent is a thionating compound that can convert a carbonyl group into a thiocarbonyl analogue by replacing oxygen atoms with sulphur. Herein, ester-functionalised coumarin compounds <strong>S1a</strong> and <strong>S2a</strong> were successfully mono-substituted and disubstituted with sulphur atoms using Lawesson's reagent. It was noted that the lactone carbonyl was first substituted, resulting in the mono-substituted analogues <strong>S1b</strong> and <strong>S2b</strong>, followed by the formation of disubstituted derivatives <strong>S1c</strong> and <strong>S2c</strong>. The thionated compounds were separated using preparative TLC with a dichloromethane: petroleum ether mixture as the mobile phase. NMR and FT-IR spectroscopies were utilised to identify and confirm the compounds isolated from the thionation reaction. The thioanalogues were then tested as potential chemosensors for metal ion detection in an acetonitrile solvent system. The results showed unique selectivities, with the unsubstituted derivatives displaying selectivities for Fe<small><sup>2+</sup></small> and Fe<small><sup>3+</sup></small>. In contrast, the mono-substituted and disubstituted derivatives were selective for Hg<small><sup>2+</sup></small> and Cu<small><sup>2+</sup></small>, demonstrating the prospective applications of these compounds as chemosensors for these metal ions.</p>","PeriodicalId":95,"journal":{"name":"New Journal of Chemistry","volume":" 5","pages":" 1745-1754"},"PeriodicalIF":2.5000,"publicationDate":"2024-12-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.rsc.org/en/content/articlepdf/2025/nj/d4nj05130k?page=search","citationCount":"0","resultStr":"{\"title\":\"Synthesis of thiocarbonyl analogues of colourimetric coumarin-based chemosensors: altering the selectivity from Fe to Hg(ii) and Cu(ii) ions†\",\"authors\":\"Stiaan Schoeman, Neliswa Mama and Lisa Myburgh\",\"doi\":\"10.1039/D4NJ05130K\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p >Lawesson's reagent is a thionating compound that can convert a carbonyl group into a thiocarbonyl analogue by replacing oxygen atoms with sulphur. Herein, ester-functionalised coumarin compounds <strong>S1a</strong> and <strong>S2a</strong> were successfully mono-substituted and disubstituted with sulphur atoms using Lawesson's reagent. It was noted that the lactone carbonyl was first substituted, resulting in the mono-substituted analogues <strong>S1b</strong> and <strong>S2b</strong>, followed by the formation of disubstituted derivatives <strong>S1c</strong> and <strong>S2c</strong>. The thionated compounds were separated using preparative TLC with a dichloromethane: petroleum ether mixture as the mobile phase. NMR and FT-IR spectroscopies were utilised to identify and confirm the compounds isolated from the thionation reaction. The thioanalogues were then tested as potential chemosensors for metal ion detection in an acetonitrile solvent system. The results showed unique selectivities, with the unsubstituted derivatives displaying selectivities for Fe<small><sup>2+</sup></small> and Fe<small><sup>3+</sup></small>. In contrast, the mono-substituted and disubstituted derivatives were selective for Hg<small><sup>2+</sup></small> and Cu<small><sup>2+</sup></small>, demonstrating the prospective applications of these compounds as chemosensors for these metal ions.</p>\",\"PeriodicalId\":95,\"journal\":{\"name\":\"New Journal of Chemistry\",\"volume\":\" 5\",\"pages\":\" 1745-1754\"},\"PeriodicalIF\":2.5000,\"publicationDate\":\"2024-12-23\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"https://pubs.rsc.org/en/content/articlepdf/2025/nj/d4nj05130k?page=search\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"New Journal of Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://pubs.rsc.org/en/content/articlelanding/2025/nj/d4nj05130k\",\"RegionNum\":3,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"New Journal of Chemistry","FirstCategoryId":"92","ListUrlMain":"https://pubs.rsc.org/en/content/articlelanding/2025/nj/d4nj05130k","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
Synthesis of thiocarbonyl analogues of colourimetric coumarin-based chemosensors: altering the selectivity from Fe to Hg(ii) and Cu(ii) ions†
Lawesson's reagent is a thionating compound that can convert a carbonyl group into a thiocarbonyl analogue by replacing oxygen atoms with sulphur. Herein, ester-functionalised coumarin compounds S1a and S2a were successfully mono-substituted and disubstituted with sulphur atoms using Lawesson's reagent. It was noted that the lactone carbonyl was first substituted, resulting in the mono-substituted analogues S1b and S2b, followed by the formation of disubstituted derivatives S1c and S2c. The thionated compounds were separated using preparative TLC with a dichloromethane: petroleum ether mixture as the mobile phase. NMR and FT-IR spectroscopies were utilised to identify and confirm the compounds isolated from the thionation reaction. The thioanalogues were then tested as potential chemosensors for metal ion detection in an acetonitrile solvent system. The results showed unique selectivities, with the unsubstituted derivatives displaying selectivities for Fe2+ and Fe3+. In contrast, the mono-substituted and disubstituted derivatives were selective for Hg2+ and Cu2+, demonstrating the prospective applications of these compounds as chemosensors for these metal ions.