Facile single-step synthesis of pentaaryl-substituted pyrano[3,2-b]pyrrol-5(1H)-ones showing aggregation-induced emission†

IF 4.7 1区 化学 Q1 CHEMISTRY, ORGANIC
Yongfeng Wang, Ruijun Chu, Yanxiao Wang, Mengyuan Zhou, Yuan Chen, Cheng Xu, Jingyu Sun and Guodong Yin
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引用次数: 0

Abstract

The continuing desire for multifunctional AIE materials has stimulated intensified research efforts to develop both innovative synthetic techniques and novel scaffolds. Herein, we report a new class of heterocyclic AIEgens, 1,2,3,6,7-pentaaryl substituted pyrano[3,2-b]pyrrol-5(1H)-ones, which contain an intriguing fused pyrrole/α-pyrone core. These structurally novel molecules were efficiently constructed via multicomponent reactions of easily accessible isatins, 2,3-diaryl cyclopropenones, and alkyl bromides in a single step under metal-free conditions. Subsequent late-stage modification of the resulting products was performed via the Suzuki–Miyaura coupling and reduction reactions. Furthermore, the HOMO/LUMO gaps were calculated and the single crystal structural analyses were conducted in order to gain deeper insights into the photophysical properties of these propeller-like AIEgens.

Abstract Image

显示聚集诱导发射的五芳基取代吡喃并[3,2-b]吡咯-5(1H)-酮的简便单步合成方法
对多功能 AIE 材料的持续渴求激发了对创新合成技术和新型支架的深入研究。在此,我们报告了一类新的杂环 AIEgens,即 1,2,3,6,7-五芳基取代吡喃并[3,2-b]吡咯-5(1H)-酮,其中含有创新的融合吡咯/α-吡酮核心。这些结构新颖的分子是在无金属条件下,通过容易获得的异汀类、2,3-二芳基环丙烯酮和烷基溴化物的多组分反应一步法高效构建的。随后通过铃木-宫浦偶联反应和还原反应对所得产物进行后期修饰。此外,还计算了 HOMO/LUMO 间隙并进行了单晶结构分析,以深入了解这些螺旋桨状 AIEgens 的光物理特性。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
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来源期刊
Organic Chemistry Frontiers
Organic Chemistry Frontiers CHEMISTRY, ORGANIC-
CiteScore
7.90
自引率
11.10%
发文量
686
审稿时长
1 months
期刊介绍: Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.
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