Tim Lippold, Julia Kosolapowa, Niko T Flosbach, Robert Herzhoff, Axel Griesbeck, Mathias Siegfried Wickleder
{"title":"Thiolate-CLPG (Chemiluminescent Protecting Groups) based on coumaranone thiolcarbamates","authors":"Tim Lippold, Julia Kosolapowa, Niko T Flosbach, Robert Herzhoff, Axel Griesbeck, Mathias Siegfried Wickleder","doi":"10.1039/d4cc06150k","DOIUrl":null,"url":null,"abstract":"The base-induced oxidative release of aromatic and aliphatic thiols from novel coumaranone-thiolurethanes 3a-3e is quantitative and accompanied by blue or green light chemiluminescence which is long-lasting over the total release period. Thus, these compounds serve as base-oxidation-labile protecting groups that decompose with strong visible luminescence and subsequent release of the protected thiolate as leaving group. Thiolate release and CL are timely decoupled for aliphatic substituted compounds 3c-3e but appear to compete for aromatic compounds 3a,b which leads to a decrease in CL intensities.","PeriodicalId":67,"journal":{"name":"Chemical Communications","volume":"9 1","pages":""},"PeriodicalIF":4.3000,"publicationDate":"2025-01-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Chemical Communications","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1039/d4cc06150k","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
Abstract
The base-induced oxidative release of aromatic and aliphatic thiols from novel coumaranone-thiolurethanes 3a-3e is quantitative and accompanied by blue or green light chemiluminescence which is long-lasting over the total release period. Thus, these compounds serve as base-oxidation-labile protecting groups that decompose with strong visible luminescence and subsequent release of the protected thiolate as leaving group. Thiolate release and CL are timely decoupled for aliphatic substituted compounds 3c-3e but appear to compete for aromatic compounds 3a,b which leads to a decrease in CL intensities.
期刊介绍:
ChemComm (Chemical Communications) is renowned as the fastest publisher of articles providing information on new avenues of research, drawn from all the world''s major areas of chemical research.