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Concise Four‐component Synthesis of Solid‐state Fluorescent α‐Sulfenylated Enaminones
European Journal of Organic Chemistry ( IF 2.5 ) Pub Date : 2024-12-23 , DOI: 10.1002/ejoc.202401308
Gereon Hendrik Schmitz, Wiebke Kramer, Leonard Karl, Christian Ganter, Thomas J. J. Müller

Acid chlorides, alkynes, amines, and N‐thiosuccinimides react in a consecutive four‐component alkynylation‐addition‐sulfenylation sequence to give α‐sulfenylated enaminones in good to excellent yields. The terminal sulfenylation step is catalyzed by Yb(OTf)3 and both N‐arylthiosuccinimides and N‐alkylthio succinimides can be successfully employed. Most products are solid‐state luminescent with fluorescence quantum yields up to 84% and lifetimes up to 4.9 ns. Additionally, TD‐DFT calculations rationalize the electronic structure of the absorption characteristics of the dyes.

中文翻译:


固体荧光 α-亚磺酰化烯胺的简明四组分合成



酰氯、炔烃、胺和 N-硫代琥珀酰亚胺以连续的四组分炔基化-加成-次磺酰化序列反应,得到α-亚磺酰化烯胺,产率从良好到极好。末端亚磺酰化步骤由 Yb(OTf)3 催化,N-芳基硫代琥珀酰亚胺和 N-烷基硫代琥珀酰亚胺都可以成功使用。大多数产品是固态发光的,荧光量子产率高达 84%,使用寿命长达 4.9 ns。此外,TD-DFT 计算使染料吸收特性的电子结构合理化。
更新日期:2024-12-23
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