A robust PET-based chiral Schiff base molecular probe for recognition of Hg2+ and Pb2+ and its application in live cell imaging†

IF 2.7 3区化学 Q2 CHEMISTRY, ANALYTICAL

Analytical Methods Pub Date : 2025-02-11 DOI:10.1039/D5AY00098J

S. Benita Jeba Silviya, S. Michlin Ruphina Maragatham, S. G. Jebastin Andrews, Nattamai S. P. Bhuvanesh, J. Winfred Jebaraj and Chithiraivel Balakrishnan

{"title":"A robust PET-based chiral Schiff base molecular probe for recognition of Hg2+ and Pb2+ and its application in live cell imaging†","authors":"S. Benita Jeba Silviya, S. Michlin Ruphina Maragatham, S. G. Jebastin Andrews, Nattamai S. P. Bhuvanesh, J. Winfred Jebaraj and Chithiraivel Balakrishnan","doi":"10.1039/D5AY00098J","DOIUrl":null,"url":null,"abstract":"A new salen-based chiral Schiff base, 6,6′-((1E,1′E)-((1R,2R)-cyclohexane-1,2-diylbis(azanylylidene))bis(methanylylidene))bis(2,4-dibromophenol) (H2L) has been designed and synthesized. H2L is a fluorescent chemical sensor that can rapidly and precisely detect harmful heavy metal ions such as Hg2+ and Pb2+ with well-separated excitation and emission wavelengths. Single-crystal X-ray diffraction analysis confirmed the structure of H2L. The binding of Hg2+/Pb2+ causes a change in the emission behavior of H2L from weakly fluorescent to highly fluorescent through the CHEF effect and inhibits the PET process. H2L exhibited immense selectivity and tremendous sensitivity, with LOD values of 8.29 nM and 7.65 nM for Hg2+ and Pb2+, respectively. The 1 : 1 binding mode of H2L·Hg2+ and H2L·Pb2+ is validated by using Job's plot, 1H NMR titration, and ESI-MS investigations. In addition, H2L has been used to detect Hg2+/Pb2+ ions in real water samples and paper strips, and intracellularly in HeLa cells.","PeriodicalId":64,"journal":{"name":"Analytical Methods","volume":" 10","pages":" 2342-2354"},"PeriodicalIF":2.7000,"publicationDate":"2025-02-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Analytical Methods","FirstCategoryId":"92","ListUrlMain":"https://pubs.rsc.org/en/content/articlelanding/2025/ay/d5ay00098j","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, ANALYTICAL","Score":null,"Total":0}

引用次数: 0

Abstract

A new salen-based chiral Schiff base, 6,6′-((1E,1′E)-((1R,2R)-cyclohexane-1,2-diylbis(azanylylidene))bis(methanylylidene))bis(2,4-dibromophenol) (H₂L) has been designed and synthesized. H₂L is a fluorescent chemical sensor that can rapidly and precisely detect harmful heavy metal ions such as Hg²⁺ and Pb²⁺ with well-separated excitation and emission wavelengths. Single-crystal X-ray diffraction analysis confirmed the structure of H₂L. The binding of Hg²⁺/Pb²⁺ causes a change in the emission behavior of H₂L from weakly fluorescent to highly fluorescent through the CHEF effect and inhibits the PET process. H₂L exhibited immense selectivity and tremendous sensitivity, with LOD values of 8.29 nM and 7.65 nM for Hg²⁺ and Pb²⁺, respectively. The 1 : 1 binding mode of H₂L·Hg²⁺ and H₂L·Pb²⁺ is validated by using Job's plot, ¹H NMR titration, and ESI-MS investigations. In addition, H₂L has been used to detect Hg²⁺/Pb²⁺ ions in real water samples and paper strips, and intracellularly in HeLa cells.