Discriminative fluorescent sensing of nitro-antibiotics at ppb level using N-phenyl-amino-1,8-naphthalimides chemosensors
The design of suitable fluorescent chemosensors for the trace detection of emerging organic pollutants attracted great research interest because of their serious menace to the environment and health hazards. Herein, we report two 1,8-naphthalimide-based fluorescent chemosensors, N-phenyl-4-amino-1,8...
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| Language: | English |
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Elsevier
2022-01-01
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| Series: | Results in Chemistry |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S221171562200265X |
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| author | Ananthu Shanmughan Pandi Raja Lakshmi Deivasigamani Umadevi Sankarasekaran Shanmugaraju |
| author_facet | Ananthu Shanmughan Pandi Raja Lakshmi Deivasigamani Umadevi Sankarasekaran Shanmugaraju |
| author_sort | Ananthu Shanmughan |
| collection | DOAJ |
| description | The design of suitable fluorescent chemosensors for the trace detection of emerging organic pollutants attracted great research interest because of their serious menace to the environment and health hazards. Herein, we report two 1,8-naphthalimide-based fluorescent chemosensors, N-phenyl-4-amino-1,8-naphthalimide (Nap-1) and N-phenyl-3-amino-1,8-naphthalimide (Nap-2), for the discriminative fluorescent sensing of nitro-containing antibiotics. Nap-1 and Nap-2 have been synthesized in two steps from their respective nitro-1,8-naphthalic anhydride precursors and they were fully characterized using standard spectroscopic techniques such as FT-IR, and NMR (1H, and 13C), and HRMS. Both Nap-1 and Nap-2 are highly emissive due to internal-charge transfer (ICT) transition and exhibited a positive solvatochromism in different solvent mediums. The fluorescence titration studies of Nap-1 and Nap-2 with various antibiotics showed high selectivity and strong binding affinity for nitro-containing antibiotics with a parts-per-billions (ppb) level of sensitivity. The initial fluorescence emission intensity of Nap-1 and Nap-2 was quenched upon the addition of nitro-antibiotics such as Nitrofurazone (NFZ) and Dimetridazole (DMZ). Notably, the co-existence of other competing antibiotics showed negligible to moderate fluorescence quenching. The observed discriminative fluorescence sensing was also reflected by sharp visual colour changes. The Stern-Volmer quenching constants (KSV) were calculated to be in the order of 104 M−1. These studies suggest that Nap-1 and Nap-2 can be used as potential “turn-off” fluorescent chemosensors for the selective, sensitive, and fast detection of nitro-antibiotics. |
| first_indexed | 2024-04-11T12:52:42Z |
| format | Article |
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| institution | Directory Open Access Journal |
| issn | 2211-7156 |
| language | English |
| last_indexed | 2024-04-11T12:52:42Z |
| publishDate | 2022-01-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Results in Chemistry |
| spelling | doaj.art-4c5b6da6a8f54bdab37c72be95dc61ee2022-12-22T04:23:10ZengElsevierResults in Chemistry2211-71562022-01-014100546Discriminative fluorescent sensing of nitro-antibiotics at ppb level using N-phenyl-amino-1,8-naphthalimides chemosensorsAnanthu Shanmughan0Pandi Raja Lakshmi1Deivasigamani Umadevi2Sankarasekaran Shanmugaraju3Department of Chemistry, Indian Institute of Technology Palakkad, Palakkad 678557, Kerala, IndiaDepartment of Chemistry, Indian Institute of Technology Palakkad, Palakkad 678557, Kerala, IndiaDepartment of Chemistry, Indian Institute of Technology Palakkad, Palakkad 678557, Kerala, IndiaCorresponding author.; Department of Chemistry, Indian Institute of Technology Palakkad, Palakkad 678557, Kerala, IndiaThe design of suitable fluorescent chemosensors for the trace detection of emerging organic pollutants attracted great research interest because of their serious menace to the environment and health hazards. Herein, we report two 1,8-naphthalimide-based fluorescent chemosensors, N-phenyl-4-amino-1,8-naphthalimide (Nap-1) and N-phenyl-3-amino-1,8-naphthalimide (Nap-2), for the discriminative fluorescent sensing of nitro-containing antibiotics. Nap-1 and Nap-2 have been synthesized in two steps from their respective nitro-1,8-naphthalic anhydride precursors and they were fully characterized using standard spectroscopic techniques such as FT-IR, and NMR (1H, and 13C), and HRMS. Both Nap-1 and Nap-2 are highly emissive due to internal-charge transfer (ICT) transition and exhibited a positive solvatochromism in different solvent mediums. The fluorescence titration studies of Nap-1 and Nap-2 with various antibiotics showed high selectivity and strong binding affinity for nitro-containing antibiotics with a parts-per-billions (ppb) level of sensitivity. The initial fluorescence emission intensity of Nap-1 and Nap-2 was quenched upon the addition of nitro-antibiotics such as Nitrofurazone (NFZ) and Dimetridazole (DMZ). Notably, the co-existence of other competing antibiotics showed negligible to moderate fluorescence quenching. The observed discriminative fluorescence sensing was also reflected by sharp visual colour changes. The Stern-Volmer quenching constants (KSV) were calculated to be in the order of 104 M−1. These studies suggest that Nap-1 and Nap-2 can be used as potential “turn-off” fluorescent chemosensors for the selective, sensitive, and fast detection of nitro-antibiotics.http://www.sciencedirect.com/science/article/pii/S221171562200265XAmino-1,8-NaphtalimidesFluorescenceSolvatochromismChemosensorsAntibioticsNitrofurantoin |
| spellingShingle | Ananthu Shanmughan Pandi Raja Lakshmi Deivasigamani Umadevi Sankarasekaran Shanmugaraju Discriminative fluorescent sensing of nitro-antibiotics at ppb level using N-phenyl-amino-1,8-naphthalimides chemosensors Results in Chemistry Amino-1,8-Naphtalimides Fluorescence Solvatochromism Chemosensors Antibiotics Nitrofurantoin |
| title | Discriminative fluorescent sensing of nitro-antibiotics at ppb level using N-phenyl-amino-1,8-naphthalimides chemosensors |
| title_full | Discriminative fluorescent sensing of nitro-antibiotics at ppb level using N-phenyl-amino-1,8-naphthalimides chemosensors |
| title_fullStr | Discriminative fluorescent sensing of nitro-antibiotics at ppb level using N-phenyl-amino-1,8-naphthalimides chemosensors |
| title_full_unstemmed | Discriminative fluorescent sensing of nitro-antibiotics at ppb level using N-phenyl-amino-1,8-naphthalimides chemosensors |
| title_short | Discriminative fluorescent sensing of nitro-antibiotics at ppb level using N-phenyl-amino-1,8-naphthalimides chemosensors |
| title_sort | discriminative fluorescent sensing of nitro antibiotics at ppb level using n phenyl amino 1 8 naphthalimides chemosensors |
| topic | Amino-1,8-Naphtalimides Fluorescence Solvatochromism Chemosensors Antibiotics Nitrofurantoin |
| url | http://www.sciencedirect.com/science/article/pii/S221171562200265X |
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