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杂芳基稠合三氮杂戊搭烯:合成与聚集诱导发光

Heteroaryl-Fused Triazapentalenes: Synthesis and Aggregation-Induced Emission.

作者信息

Wang Yingchun, Pham Thanh Chung, Huang Jianjun, Wu Junfeng, Dehaen Wim

机构信息

Henan Key Laboratory of Water Pollution Control and Rehabilitation Technology, Henan University of Urban Construction, Pingdingshan 467036, China.

Sustainable Chemistry for Metals and Molecules, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, 3001 Leuven, Belgium.

出版信息

Molecules. 2025 Jan 3;30(1):156. doi: 10.3390/molecules30010156.

DOI:10.3390/molecules30010156
PMID:39795212
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11721409/
Abstract

A pyridine-fused triazapentalene shows weak fluorescence in solution and is readily accessible via nitrene-mediated cyclization. In this study, a modified Cadogan reaction was used to synthesize . Palladium-catalyzed reactions have been used as post-functionalization methods. Interestingly, modified Suzuki cross-couplings with various boronic acids resulted in poor to moderate yields of - which were arylated at the azole moiety. Direct CH arylation of gave the products with the same regiochemistry in satisfactory yields. The structures of - were confirmed using NMR analysis. In addition, the photophysical properties of - were studied under various conditions. Particularly, the emission of - is enhanced in the solid and aggregate state.

摘要

一种吡啶稠合的三氮杂戊搭烯在溶液中显示出微弱的荧光,并且可以通过氮烯介导的环化反应轻松获得。在本研究中,采用改良的卡多根反应来合成 。钯催化反应已被用作后官能团化方法。有趣的是,与各种硼酸进行的改良铃木交叉偶联反应得到的 - 的产率较低至中等, - 在唑部分发生芳基化。 的直接C-H芳基化反应以令人满意的产率得到具有相同区域化学的产物。通过核磁共振分析确认了 - 的结构。此外,还研究了 - 在各种条件下的光物理性质。特别地, - 在固态和聚集态下的发射增强。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d24b/11721409/df228f38d473/molecules-30-00156-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d24b/11721409/bb6d7cb45cfd/molecules-30-00156-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d24b/11721409/6d281a772ea2/molecules-30-00156-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d24b/11721409/994a1042e24a/molecules-30-00156-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d24b/11721409/597c75e4d2a5/molecules-30-00156-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d24b/11721409/df228f38d473/molecules-30-00156-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d24b/11721409/bb6d7cb45cfd/molecules-30-00156-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d24b/11721409/6d281a772ea2/molecules-30-00156-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d24b/11721409/994a1042e24a/molecules-30-00156-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d24b/11721409/597c75e4d2a5/molecules-30-00156-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d24b/11721409/df228f38d473/molecules-30-00156-g003.jpg

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