{"title":"Effect of π-Electron Conjugation on the Chiroptical Properties of Helicene Carbon Nanohoops","authors":"Kovida Kovida, Juraj Malinčík, Tomáš Šolomek","doi":"10.1002/hlca.202400166","DOIUrl":null,"url":null,"abstract":"<p>We designed, synthesized, and investigated a new chiral carbon nanohoop that formally incorporates a benzothiadiazole and [5]helicene units into the structure of [6]cycloparaphenylene. The connection of these units in the chiral nanohoop is designed to allow for π-electron conjugation between the benzothiadiazole chromophore and the chirality-inducing [5]helicene. We resolved the enantiomers of the highly fluorescent, near-IR light emitting benzothiadiazole helicene nanohoop. Electronic circular dichroism spectroscopy then allowed us to investigate whether the selected molecular design leads to an increase in the lowest singlet excited state delocalization to improve the compound's electronic dissymmetry factor in comparison to the previously studied benzothiadiazole carbon nanohoop with planar chiral [2.2]paracyclophane unit with <i>pseudo-meta</i> connection.</p>","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":"108 4","pages":""},"PeriodicalIF":1.5000,"publicationDate":"2025-01-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/hlca.202400166","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Helvetica Chimica Acta","FirstCategoryId":"92","ListUrlMain":"https://onlinelibrary.wiley.com/doi/10.1002/hlca.202400166","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
Abstract
We designed, synthesized, and investigated a new chiral carbon nanohoop that formally incorporates a benzothiadiazole and [5]helicene units into the structure of [6]cycloparaphenylene. The connection of these units in the chiral nanohoop is designed to allow for π-electron conjugation between the benzothiadiazole chromophore and the chirality-inducing [5]helicene. We resolved the enantiomers of the highly fluorescent, near-IR light emitting benzothiadiazole helicene nanohoop. Electronic circular dichroism spectroscopy then allowed us to investigate whether the selected molecular design leads to an increase in the lowest singlet excited state delocalization to improve the compound's electronic dissymmetry factor in comparison to the previously studied benzothiadiazole carbon nanohoop with planar chiral [2.2]paracyclophane unit with pseudo-meta connection.
期刊介绍：
Helvetica Chimica Acta, founded by the Swiss Chemical Society in 1917, is a monthly multidisciplinary journal dedicated to the dissemination of knowledge in all disciplines of chemistry (organic, inorganic, physical, technical, theoretical and analytical chemistry) as well as research at the interface with other sciences, where molecular aspects are key to the findings. Helvetica Chimica Acta is committed to the publication of original, high quality papers at the frontier of scientific research. All contributions will be peer reviewed with the highest possible standards and published within 3 months of receipt, with no restriction on the length of the papers and in full color.
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