Yongfeng Wang, Ruijun Chu, Yanxiao Wang, Mengyuan Zhou, Yuan Chen, Cheng Xu, Jingyu Sun and Guodong Yin
{"title":"Facile single-step synthesis of pentaaryl-substituted pyrano[3,2-b]pyrrol-5(1H)-ones showing aggregation-induced emission†","authors":"Yongfeng Wang, Ruijun Chu, Yanxiao Wang, Mengyuan Zhou, Yuan Chen, Cheng Xu, Jingyu Sun and Guodong Yin","doi":"10.1039/D4QO01600A","DOIUrl":null,"url":null,"abstract":"<p >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-<em>b</em>]pyrrol-5(1<em>H</em>)-ones, which contain an intriguing fused pyrrole/α-pyrone core. These structurally novel molecules were efficiently constructed <em>via</em> 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 <em>via</em> 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.</p>","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":" 1","pages":" 209-216"},"PeriodicalIF":4.7000,"publicationDate":"2024-10-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Chemistry Frontiers","FirstCategoryId":"92","ListUrlMain":"https://pubs.rsc.org/en/content/articlelanding/2025/qo/d4qo01600a","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
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.
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.