Design, synthesis, and photophysical characterization of monoaryl-pyridine-2-ones derivatives: Exploring aggregation-caused quenching vs aggregation-induced emission
Murugesan Preethi, Ajay Dev Ramesh Babu, Sivakumar Shanmugam
{"title":"Design, synthesis, and photophysical characterization of monoaryl-pyridine-2-ones derivatives: Exploring aggregation-caused quenching vs aggregation-induced emission","authors":"Murugesan Preethi, Ajay Dev Ramesh Babu, Sivakumar Shanmugam","doi":"10.1016/j.tet.2025.134773","DOIUrl":null,"url":null,"abstract":"<div><div>The dihydropyridine core derivatives have been synthesized from the reaction of 2H-pyrone with hydrazine hydrate, in methanol ethanol solvent, obtained 70–90 %. Under the reflux condition occurred withopening of the lactone ring to yield monoaryl-pyridine-2-ones derivatives <strong>3a-d</strong> in excellent yields. This method's main advantages are short reaction time, high amine utilization, and considerably improved yield. The emission of the molecules 3d can be significantly quenched by picric acid through electron transfer or energy transfer mechanisms, enabling them to function as chemosensors for explosive nitroaryl compound detection.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"184 ","pages":"Article 134773"},"PeriodicalIF":2.1000,"publicationDate":"2025-06-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Tetrahedron","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0040402025003291","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
The dihydropyridine core derivatives have been synthesized from the reaction of 2H-pyrone with hydrazine hydrate, in methanol ethanol solvent, obtained 70–90 %. Under the reflux condition occurred withopening of the lactone ring to yield monoaryl-pyridine-2-ones derivatives 3a-d in excellent yields. This method's main advantages are short reaction time, high amine utilization, and considerably improved yield. The emission of the molecules 3d can be significantly quenched by picric acid through electron transfer or energy transfer mechanisms, enabling them to function as chemosensors for explosive nitroaryl compound detection.
期刊介绍:
Tetrahedron publishes full accounts of research having outstanding significance in the broad field of organic chemistry and its related disciplines, such as organic materials and bio-organic chemistry.
Regular papers in Tetrahedron are expected to represent detailed accounts of an original study having substantially greater scope and details than that found in a communication, as published in Tetrahedron Letters.
Tetrahedron also publishes thematic collections of papers as special issues and ''Reports'', commissioned in-depth reviews providing a comprehensive overview of a research area.