Highly emissive pyrrolo[1,2-a]quinoxaline based narrow band fluorescent sensors for detection of nitroaromatics and their application in spot paper test
In the modern day, explosive detection is essential to public safety, and fluorescent small molecules have gained popularity for their quick and accurate detection. Herein, we present the design and synthesis of a series of pyrrolo[1,2-a]quinoxaline-based conjugated small organic fluorophores (PQ-Ph...
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| Format: | Article |
| Language: | English |
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Elsevier
2024-06-01
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| Series: | Chemical Physics Impact |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2667022424001129 |
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| author | Aniket Karpe Aniket Parab Gokul Ganesan Jatin Lade Pravin Walke Atul Chaskar |
| author_facet | Aniket Karpe Aniket Parab Gokul Ganesan Jatin Lade Pravin Walke Atul Chaskar |
| author_sort | Aniket Karpe |
| collection | DOAJ |
| description | In the modern day, explosive detection is essential to public safety, and fluorescent small molecules have gained popularity for their quick and accurate detection. Herein, we present the design and synthesis of a series of pyrrolo[1,2-a]quinoxaline-based conjugated small organic fluorophores (PQ-Ph-OH, PQ-Ph-NMe, PQ-Ph-OMe, PQ-Ph-Me, and PQ-Ph-CN) as fluorescence-based sensors for explosive molecules. The sensor molecules were synthesized in good to excellent yields using a dehomologative functionalization strategy. They exhibited excellent photophysical characteristics, which was tunable based on the substituent on the phenyl linker at position 3. DFT studies showed that the pyrroloquinoxaline moiety could act as an on-demand electron donor or acceptor, depending on the phenyl substituent. The molecules also exhibited solid state emission due to twisted geometry around the CC single bond between the heterocyclic scaffold and the phenyl derivative. This resulted in low band intense emission for the synthesized molecules. In the presence of electron-deficient nitroaromatic explosives, all the fluorophores showed excellent fluorescence quenching. Detection limits in the range of 10−4 M were obtained for all the fluorophores. Stern-Volmer plots show high values of binding constants, indicating good interaction between the fluorophores and the explosive molecules. The mechanism of sensing was confirmed by UV-PL spectral overlap and fluorescence lifetime measurements, which suggest a static quenching based on the formation of a ground state complex. Owing to solid state emissions in some of the derivatives, the synthesized molecules were applied to paper strips for spot detection of explosive molecules. |
| first_indexed | 2024-04-24T19:48:25Z |
| format | Article |
| id | doaj.art-547459fb9ccb4a87b6e37f94b2d45d81 |
| institution | Directory Open Access Journal |
| issn | 2667-0224 |
| language | English |
| last_indexed | 2024-04-24T19:48:25Z |
| publishDate | 2024-06-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Chemical Physics Impact |
| spelling | doaj.art-547459fb9ccb4a87b6e37f94b2d45d812024-03-25T04:18:08ZengElsevierChemical Physics Impact2667-02242024-06-018100568Highly emissive pyrrolo[1,2-a]quinoxaline based narrow band fluorescent sensors for detection of nitroaromatics and their application in spot paper testAniket Karpe0Aniket Parab1Gokul Ganesan2Jatin Lade3Pravin Walke4Atul Chaskar5National Centre for Nanosciences & Nanotechnology, University of Mumbai, Vidyanagari, Mumbai 400098, Maharashtra, IndiaNational Centre for Nanosciences & Nanotechnology, University of Mumbai, Vidyanagari, Mumbai 400098, Maharashtra, IndiaNational Centre for Nanosciences & Nanotechnology, University of Mumbai, Vidyanagari, Mumbai 400098, Maharashtra, IndiaNational Centre for Nanosciences & Nanotechnology, University of Mumbai, Vidyanagari, Mumbai 400098, Maharashtra, IndiaNational Centre for Nanosciences & Nanotechnology, University of Mumbai, Vidyanagari, Mumbai 400098, Maharashtra, India; Corresponding author.National Centre for Nanosciences & Nanotechnology, University of Mumbai, Vidyanagari, Mumbai 400098, Maharashtra, India; Department of Chemistry, Institute of Chemical Technology, N.P.Marg, Matunga, Mumbai 400019, Maharashtra, India; Corresponding author.In the modern day, explosive detection is essential to public safety, and fluorescent small molecules have gained popularity for their quick and accurate detection. Herein, we present the design and synthesis of a series of pyrrolo[1,2-a]quinoxaline-based conjugated small organic fluorophores (PQ-Ph-OH, PQ-Ph-NMe, PQ-Ph-OMe, PQ-Ph-Me, and PQ-Ph-CN) as fluorescence-based sensors for explosive molecules. The sensor molecules were synthesized in good to excellent yields using a dehomologative functionalization strategy. They exhibited excellent photophysical characteristics, which was tunable based on the substituent on the phenyl linker at position 3. DFT studies showed that the pyrroloquinoxaline moiety could act as an on-demand electron donor or acceptor, depending on the phenyl substituent. The molecules also exhibited solid state emission due to twisted geometry around the CC single bond between the heterocyclic scaffold and the phenyl derivative. This resulted in low band intense emission for the synthesized molecules. In the presence of electron-deficient nitroaromatic explosives, all the fluorophores showed excellent fluorescence quenching. Detection limits in the range of 10−4 M were obtained for all the fluorophores. Stern-Volmer plots show high values of binding constants, indicating good interaction between the fluorophores and the explosive molecules. The mechanism of sensing was confirmed by UV-PL spectral overlap and fluorescence lifetime measurements, which suggest a static quenching based on the formation of a ground state complex. Owing to solid state emissions in some of the derivatives, the synthesized molecules were applied to paper strips for spot detection of explosive molecules.http://www.sciencedirect.com/science/article/pii/S2667022424001129Pyrrolo[1,2-a]quinoxalineExplosive detectionFluorescence detectionSmall organic molecules |
| spellingShingle | Aniket Karpe Aniket Parab Gokul Ganesan Jatin Lade Pravin Walke Atul Chaskar Highly emissive pyrrolo[1,2-a]quinoxaline based narrow band fluorescent sensors for detection of nitroaromatics and their application in spot paper test Chemical Physics Impact Pyrrolo[1,2-a]quinoxaline Explosive detection Fluorescence detection Small organic molecules |
| title | Highly emissive pyrrolo[1,2-a]quinoxaline based narrow band fluorescent sensors for detection of nitroaromatics and their application in spot paper test |
| title_full | Highly emissive pyrrolo[1,2-a]quinoxaline based narrow band fluorescent sensors for detection of nitroaromatics and their application in spot paper test |
| title_fullStr | Highly emissive pyrrolo[1,2-a]quinoxaline based narrow band fluorescent sensors for detection of nitroaromatics and their application in spot paper test |
| title_full_unstemmed | Highly emissive pyrrolo[1,2-a]quinoxaline based narrow band fluorescent sensors for detection of nitroaromatics and their application in spot paper test |
| title_short | Highly emissive pyrrolo[1,2-a]quinoxaline based narrow band fluorescent sensors for detection of nitroaromatics and their application in spot paper test |
| title_sort | highly emissive pyrrolo 1 2 a quinoxaline based narrow band fluorescent sensors for detection of nitroaromatics and their application in spot paper test |
| topic | Pyrrolo[1,2-a]quinoxaline Explosive detection Fluorescence detection Small organic molecules |
| url | http://www.sciencedirect.com/science/article/pii/S2667022424001129 |
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