A Novel Fluorescent Chemosensor Based on Rhodamine Schiff Base: Synthesis, Photophysical, Computational and Bioimaging Application in Live Cells
A novel rhodamine-6G derivative <b>RdN</b> was synthesized by condensing rhodamine glyoxal and 3-hydroxy-2-naphthoic hydrazide using a microwave irradiation-assisted reaction. Colorimetric and photophysical studies have demonstrated that the molecule produced can selectively sense Pb<...
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2024-12-01
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| author | Oyedoyin Aduroja Roosevelt Shaw Sisay Uota Isaac Abiye James Wachira Fasil Abebe |
| author_facet | Oyedoyin Aduroja Roosevelt Shaw Sisay Uota Isaac Abiye James Wachira Fasil Abebe |
| author_sort | Oyedoyin Aduroja |
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| description | A novel rhodamine-6G derivative <b>RdN</b> was synthesized by condensing rhodamine glyoxal and 3-hydroxy-2-naphthoic hydrazide using a microwave irradiation-assisted reaction. Colorimetric and photophysical studies have demonstrated that the molecule produced can selectively sense Pb<sup>2+</sup> and Cu<sup>2+</sup> ions in a solution of CH<sub>3</sub>CN/H<sub>2</sub>O (9:1, <i>v</i>/<i>v</i>). The spirolactam ring of <b>RdN</b> opens upon complexation with the cations, forming a highly fluorescent complex and a visible color change in the solution. The compound <b>RdN</b> was further studied with the help of computational methods such as the Density Functional Theory (DFT) method and time-dependent density theory (TD-DFT) calculations to study the binding interactions and properties of the molecule. DFT calculations and job plot data supported the 2:1 complex formation between <b>RdN</b> and Pb<sup>2+</sup>/Cu<sup>2+</sup>. The limit of detection for Pb<sup>2+</sup> was determined to be 0.112 µM and 0.130 µM for Cu<sup>2+</sup>. The probe <b>RdN</b> was applied to the image of Pb<sup>2+</sup> and Cu<sup>2+</sup> ions in living cells and is safe for biomedical applications. It is used to monitor Pb<sup>2+</sup> in environmental water samples. |
| format | Article |
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| institution | Kabale University |
| issn | 2304-6740 |
| language | English |
| publishDate | 2024-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Inorganics |
| spelling | doaj-art-0ef2d91034254cd688ce537eecb1ccce2025-01-24T13:35:27ZengMDPI AGInorganics2304-67402024-12-01131510.3390/inorganics13010005A Novel Fluorescent Chemosensor Based on Rhodamine Schiff Base: Synthesis, Photophysical, Computational and Bioimaging Application in Live CellsOyedoyin Aduroja0Roosevelt Shaw1Sisay Uota2Isaac Abiye3James Wachira4Fasil Abebe5Department of Chemistry, Morgan State University, 1700 E Cold Spring Ln, Baltimore, MD 21251, USADepartment of Chemistry, Morgan State University, 1700 E Cold Spring Ln, Baltimore, MD 21251, USADepartment of Chemistry, Morgan State University, 1700 E Cold Spring Ln, Baltimore, MD 21251, USADepartment of Chemistry, Morgan State University, 1700 E Cold Spring Ln, Baltimore, MD 21251, USADepartment of Chemistry, Morgan State University, 1700 E Cold Spring Ln, Baltimore, MD 21251, USADepartment of Chemistry, Morgan State University, 1700 E Cold Spring Ln, Baltimore, MD 21251, USAA novel rhodamine-6G derivative <b>RdN</b> was synthesized by condensing rhodamine glyoxal and 3-hydroxy-2-naphthoic hydrazide using a microwave irradiation-assisted reaction. Colorimetric and photophysical studies have demonstrated that the molecule produced can selectively sense Pb<sup>2+</sup> and Cu<sup>2+</sup> ions in a solution of CH<sub>3</sub>CN/H<sub>2</sub>O (9:1, <i>v</i>/<i>v</i>). The spirolactam ring of <b>RdN</b> opens upon complexation with the cations, forming a highly fluorescent complex and a visible color change in the solution. The compound <b>RdN</b> was further studied with the help of computational methods such as the Density Functional Theory (DFT) method and time-dependent density theory (TD-DFT) calculations to study the binding interactions and properties of the molecule. DFT calculations and job plot data supported the 2:1 complex formation between <b>RdN</b> and Pb<sup>2+</sup>/Cu<sup>2+</sup>. The limit of detection for Pb<sup>2+</sup> was determined to be 0.112 µM and 0.130 µM for Cu<sup>2+</sup>. The probe <b>RdN</b> was applied to the image of Pb<sup>2+</sup> and Cu<sup>2+</sup> ions in living cells and is safe for biomedical applications. It is used to monitor Pb<sup>2+</sup> in environmental water samples.https://www.mdpi.com/2304-6740/13/1/5microwave-assisted synthesisrhodamine 6Gcolorimetricfluorescenceprobecomputational |
| spellingShingle | Oyedoyin Aduroja Roosevelt Shaw Sisay Uota Isaac Abiye James Wachira Fasil Abebe A Novel Fluorescent Chemosensor Based on Rhodamine Schiff Base: Synthesis, Photophysical, Computational and Bioimaging Application in Live Cells Inorganics microwave-assisted synthesis rhodamine 6G colorimetric fluorescence probe computational |
| title | A Novel Fluorescent Chemosensor Based on Rhodamine Schiff Base: Synthesis, Photophysical, Computational and Bioimaging Application in Live Cells |
| title_full | A Novel Fluorescent Chemosensor Based on Rhodamine Schiff Base: Synthesis, Photophysical, Computational and Bioimaging Application in Live Cells |
| title_fullStr | A Novel Fluorescent Chemosensor Based on Rhodamine Schiff Base: Synthesis, Photophysical, Computational and Bioimaging Application in Live Cells |
| title_full_unstemmed | A Novel Fluorescent Chemosensor Based on Rhodamine Schiff Base: Synthesis, Photophysical, Computational and Bioimaging Application in Live Cells |
| title_short | A Novel Fluorescent Chemosensor Based on Rhodamine Schiff Base: Synthesis, Photophysical, Computational and Bioimaging Application in Live Cells |
| title_sort | novel fluorescent chemosensor based on rhodamine schiff base synthesis photophysical computational and bioimaging application in live cells |
| topic | microwave-assisted synthesis rhodamine 6G colorimetric fluorescence probe computational |
| url | https://www.mdpi.com/2304-6740/13/1/5 |
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