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炔基化和三唑连接的芳酰基-S,N-烯酮缩醛:具有聚集诱导增强发射特性的固态发光染料的一锅法合成。

Alkynylated and triazole-linked aroyl-S,N-ketene acetals: one-pot synthesis of solid-state emissive dyes with aggregation-induced enhanced emission characteristics.

作者信息

Biesen Lukas, Hartmann Yannic, Müller Thomas J J

机构信息

Institut für Organische Chemie und Makromolekulare Chemie, Heinrich-Heine-Universität Düsseldorf, Universitätsstraße 1, 40225, Düsseldorf, Germany.

出版信息

Sci Rep. 2023 Sep 1;13(1):14399. doi: 10.1038/s41598-023-41146-w.

DOI:10.1038/s41598-023-41146-w
PMID:37658089
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10474010/
Abstract

Alkynylated aroyl-S,N-ketene acetals are readily synthesized in mostly excellent yields by a Sonogashira reaction resulting in a substance library of more than 20 examples. Upon expansion of the reaction sequence by deprotection and concatenating of the copper-click reaction in a one-pot fashion, a library of 11 triazole-ligated aroyl-S,N-ketene acetals is readily accessible. All derivatives show pronounced solid-state emission and aggregation-induced emission properties depending on the nature of the alkynyl or the triazole substituents.

摘要

通过Sonogashira反应可轻松合成炔基化的芳酰基-S,N-烯酮缩醛,产率大多优异,得到了一个包含20多个实例的物质库。通过一锅法进行脱保护和铜催化点击反应来扩展反应序列,可轻松获得一个包含11种三唑连接的芳酰基-S,N-烯酮缩醛的文库。所有衍生物根据炔基或三唑取代基的性质表现出明显的固态发光和聚集诱导发光特性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5ee2/10474010/f213ea757037/41598_2023_41146_Fig7_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5ee2/10474010/bff27cc8da85/41598_2023_41146_Fig1_HTML.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5ee2/10474010/d5a2ed4624dc/41598_2023_41146_Fig5_HTML.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5ee2/10474010/f213ea757037/41598_2023_41146_Fig7_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5ee2/10474010/bff27cc8da85/41598_2023_41146_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5ee2/10474010/4663b8217f57/41598_2023_41146_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5ee2/10474010/99134c7854f6/41598_2023_41146_Fig3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5ee2/10474010/6bb973b73c59/41598_2023_41146_Fig4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5ee2/10474010/d5a2ed4624dc/41598_2023_41146_Fig5_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5ee2/10474010/fc6af429251e/41598_2023_41146_Fig6_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5ee2/10474010/f213ea757037/41598_2023_41146_Fig7_HTML.jpg

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The 2022 Nobel Prize in Chemistry for the development of click chemistry and bioorthogonal chemistry.
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