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Selective Detection of Trinitrophenol by Amphiphilic Dimethylaminopyridine-Appended Zn(II)phthalocyanines at the Near-Infrared Region
[Image: see text] Novel amphiphilic Zn(II)phthalocyanines (ZnPcs) peripherally substituted with four and eight dimethylaminopyridinium units (ZnPc1 and ZnPc2) were synthesized by cyclotetramerization of the corresponding phthalonitriles. The effect of aggregation and photophysical (fluorescence quan...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2019
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6648911/ https://www.ncbi.nlm.nih.gov/pubmed/31459764 http://dx.doi.org/10.1021/acsomega.8b02394 |
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author | Kasthuri, S. Gawas, Pratiksha Maji, Samarendra Veeraiah, N. Venkatramaiah, N. |
author_facet | Kasthuri, S. Gawas, Pratiksha Maji, Samarendra Veeraiah, N. Venkatramaiah, N. |
author_sort | Kasthuri, S. |
collection | PubMed |
description | [Image: see text] Novel amphiphilic Zn(II)phthalocyanines (ZnPcs) peripherally substituted with four and eight dimethylaminopyridinium units (ZnPc1 and ZnPc2) were synthesized by cyclotetramerization of the corresponding phthalonitriles. The effect of aggregation and photophysical (fluorescence quantum yields and lifetimes) and photochemical (singlet oxygen generation and photodegradation under light irradiation) properties was investigated. The chemosensing ability of ZnPcs toward explosive nitroaromatic compounds was explored in aqueous medium. This study demonstrates that ZnPc1 and ZnPc2 show fluorescence quenching behavior upon interaction with different nitro analytes and show unprecedented selectivity toward 2,4,6-trinitrophenol with a limit of detection (LOD) of 0.7–1.1 ppm with a high quenching rate constant (K(sv)) of 1.6–2.02 × 10(5). The near-infrared (NIR) fluorescence in thin films was quenched efficiently because of the photoinduced electron-transfer process through strong intermolecular π–π and electrostatic interactions. The sensing process is highly reversible and free from the interference of other commonly encountered nitro analytes. Further, experiments were performed to demonstrate the use of ZnPcs as efficient heterogeneous photocatalysts in the reduction of nitro explosives. The smart dual performance of multicharged ZnPcs in aqueous media quantifies them as attractive candidates in developing sensor materials at the NIR region and to possibly convert the toxic explosives into useful scaffolds. These results provide an interesting perspective toward elaboration of stable fluorescent systems for the selective sensing behavior of nitro explosives and their facile heterogeneous catalytic behavior in the reduction reactions. |
format | Online Article Text |
id | pubmed-6648911 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-66489112019-08-27 Selective Detection of Trinitrophenol by Amphiphilic Dimethylaminopyridine-Appended Zn(II)phthalocyanines at the Near-Infrared Region Kasthuri, S. Gawas, Pratiksha Maji, Samarendra Veeraiah, N. Venkatramaiah, N. ACS Omega [Image: see text] Novel amphiphilic Zn(II)phthalocyanines (ZnPcs) peripherally substituted with four and eight dimethylaminopyridinium units (ZnPc1 and ZnPc2) were synthesized by cyclotetramerization of the corresponding phthalonitriles. The effect of aggregation and photophysical (fluorescence quantum yields and lifetimes) and photochemical (singlet oxygen generation and photodegradation under light irradiation) properties was investigated. The chemosensing ability of ZnPcs toward explosive nitroaromatic compounds was explored in aqueous medium. This study demonstrates that ZnPc1 and ZnPc2 show fluorescence quenching behavior upon interaction with different nitro analytes and show unprecedented selectivity toward 2,4,6-trinitrophenol with a limit of detection (LOD) of 0.7–1.1 ppm with a high quenching rate constant (K(sv)) of 1.6–2.02 × 10(5). The near-infrared (NIR) fluorescence in thin films was quenched efficiently because of the photoinduced electron-transfer process through strong intermolecular π–π and electrostatic interactions. The sensing process is highly reversible and free from the interference of other commonly encountered nitro analytes. Further, experiments were performed to demonstrate the use of ZnPcs as efficient heterogeneous photocatalysts in the reduction of nitro explosives. The smart dual performance of multicharged ZnPcs in aqueous media quantifies them as attractive candidates in developing sensor materials at the NIR region and to possibly convert the toxic explosives into useful scaffolds. These results provide an interesting perspective toward elaboration of stable fluorescent systems for the selective sensing behavior of nitro explosives and their facile heterogeneous catalytic behavior in the reduction reactions. American Chemical Society 2019-04-03 /pmc/articles/PMC6648911/ /pubmed/31459764 http://dx.doi.org/10.1021/acsomega.8b02394 Text en Copyright © 2019 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes. |
spellingShingle | Kasthuri, S. Gawas, Pratiksha Maji, Samarendra Veeraiah, N. Venkatramaiah, N. Selective Detection of Trinitrophenol by Amphiphilic Dimethylaminopyridine-Appended Zn(II)phthalocyanines at the Near-Infrared Region |
title | Selective Detection of Trinitrophenol by Amphiphilic
Dimethylaminopyridine-Appended Zn(II)phthalocyanines at the Near-Infrared
Region |
title_full | Selective Detection of Trinitrophenol by Amphiphilic
Dimethylaminopyridine-Appended Zn(II)phthalocyanines at the Near-Infrared
Region |
title_fullStr | Selective Detection of Trinitrophenol by Amphiphilic
Dimethylaminopyridine-Appended Zn(II)phthalocyanines at the Near-Infrared
Region |
title_full_unstemmed | Selective Detection of Trinitrophenol by Amphiphilic
Dimethylaminopyridine-Appended Zn(II)phthalocyanines at the Near-Infrared
Region |
title_short | Selective Detection of Trinitrophenol by Amphiphilic
Dimethylaminopyridine-Appended Zn(II)phthalocyanines at the Near-Infrared
Region |
title_sort | selective detection of trinitrophenol by amphiphilic
dimethylaminopyridine-appended zn(ii)phthalocyanines at the near-infrared
region |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6648911/ https://www.ncbi.nlm.nih.gov/pubmed/31459764 http://dx.doi.org/10.1021/acsomega.8b02394 |
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