{"title":"Synthesis and fluorescence properties of 2′-benzyloxy flavone—a dual probe for selective detection of picric acid and pH sensing†","authors":"Vengatesh Gopal, Jayasankar Sudhakaran, Nirenjana Ramachandran, Thejus Kozhiyottu Mana, Aravind Remesh Kana, Anandhu Omanakuttan Nair, Priyanka Mohan, Tejaswini Madhusudhan, Sankarasekaran Shanmugaraju and Pandurangan Nanjan","doi":"10.1039/D4SD00151F","DOIUrl":null,"url":null,"abstract":"<p >Flavonoids are naturally occurring oxygen-containing heterocyclic systems with unique properties for diverse applications. The present study reports the synthesis of a new 2′-benzyloxy flavone and explores its fluorescence sensing properties towards secondary chemical explosives, such as picric acid, and pH sensing. The target 2′-benzyloxy flavone fluorophore (<strong>5</strong>) was synthesized in three-step reactions with good yield and was fully characterized using NMR, FTIR spectroscopy, and HRMS. The sensing propensity of <strong>5</strong> towards nitroaromatics and pH was probed using fluorescence spectroscopy. Compound <strong>5</strong> exhibited a preferential sensing property for phenolic nitroaromatics with high quenching efficiency for picric acid and differential fluorescence responses for different pH. The superior selectivity of <strong>5</strong> for picric acid is attributed to the intermolecular hydrogen bonding interactions between the O atoms in <strong>5</strong> and the OH groups of picric acid. The observed experimental results were further validated by computational calculations which strongly supported the hydrogen-bond-driven sensing selectivity. Furthermore, selective sensing of picric acid by <strong>5</strong> was further demonstrated in real-water samples and using paper-based sensing. These studies make compound <strong>5</strong> a potential dual sensor for selective sensing of picric acid and sensing of pH of the medium.</p>","PeriodicalId":74786,"journal":{"name":"Sensors & diagnostics","volume":null,"pages":null},"PeriodicalIF":3.5000,"publicationDate":"2024-06-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.rsc.org/en/content/articlepdf/2024/sd/d4sd00151f?page=search","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Sensors & diagnostics","FirstCategoryId":"1085","ListUrlMain":"https://pubs.rsc.org/en/content/articlelanding/2024/sd/d4sd00151f","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, ANALYTICAL","Score":null,"Total":0}
引用次数: 0
Abstract
Flavonoids are naturally occurring oxygen-containing heterocyclic systems with unique properties for diverse applications. The present study reports the synthesis of a new 2′-benzyloxy flavone and explores its fluorescence sensing properties towards secondary chemical explosives, such as picric acid, and pH sensing. The target 2′-benzyloxy flavone fluorophore (5) was synthesized in three-step reactions with good yield and was fully characterized using NMR, FTIR spectroscopy, and HRMS. The sensing propensity of 5 towards nitroaromatics and pH was probed using fluorescence spectroscopy. Compound 5 exhibited a preferential sensing property for phenolic nitroaromatics with high quenching efficiency for picric acid and differential fluorescence responses for different pH. The superior selectivity of 5 for picric acid is attributed to the intermolecular hydrogen bonding interactions between the O atoms in 5 and the OH groups of picric acid. The observed experimental results were further validated by computational calculations which strongly supported the hydrogen-bond-driven sensing selectivity. Furthermore, selective sensing of picric acid by 5 was further demonstrated in real-water samples and using paper-based sensing. These studies make compound 5 a potential dual sensor for selective sensing of picric acid and sensing of pH of the medium.