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Designing a Redox Noninnocent Phenalenyl-Based Copper(II) Complex: An Autotandem Catalyst for the Selective Oxidation of Polycyclic Aromatic Hydrocarbons (PAHs)
[Image: see text] A square-planar [Cu(II)L] complex 1, based on the redox-active phenalenyl unit LH(2) = 9,9′-(ethane-1,2-diylbis(azanediyl))bis(1H-phenalen-1-one), is prepared and structurally characterized by single-crystal X-ray diffraction analysis. Complex 1 crystallizes at room temperature wit...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2022
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8928492/ https://www.ncbi.nlm.nih.gov/pubmed/35309439 http://dx.doi.org/10.1021/acsomega.1c07051 |
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author | Kamboj, Nisha Mali, Ghanshyam Lama, Prem Erande, Rohan D. Metre, Ramesh K. |
author_facet | Kamboj, Nisha Mali, Ghanshyam Lama, Prem Erande, Rohan D. Metre, Ramesh K. |
author_sort | Kamboj, Nisha |
collection | PubMed |
description | [Image: see text] A square-planar [Cu(II)L] complex 1, based on the redox-active phenalenyl unit LH(2) = 9,9′-(ethane-1,2-diylbis(azanediyl))bis(1H-phenalen-1-one), is prepared and structurally characterized by single-crystal X-ray diffraction analysis. Complex 1 crystallizes at room temperature with the P1 space group. The molecular structure of 1 reveals the presence of intriguing C–H···Cu intermolecular anagostic interactions of the order ∼2.7715 Å. Utilizing the presence of anagostic interactions and the free nonbonding molecular orbitals (NBMOs) of the closed-shell phenalenyl unit in 1, the oxidation reactions of some industrially important polycyclic aromatic hydrocarbons (PAHs) in the presence of the [Cu(II)L] complex under very mild conditions have been reported. The direct conversion of anthracene-9-carbaldehyde to 9,10-anthraquinone in one step concludes that the catalyst shows dual activity in the chemical transformations. This also includes the first report of a “single-step” catalytic transformation of pyrene-1-carbaldehyde to the synthetically difficult pyren-4-ol, a precursor for the synthesis of several novel fluorescent probes for cell imaging. |
format | Online Article Text |
id | pubmed-8928492 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-89284922022-03-18 Designing a Redox Noninnocent Phenalenyl-Based Copper(II) Complex: An Autotandem Catalyst for the Selective Oxidation of Polycyclic Aromatic Hydrocarbons (PAHs) Kamboj, Nisha Mali, Ghanshyam Lama, Prem Erande, Rohan D. Metre, Ramesh K. ACS Omega [Image: see text] A square-planar [Cu(II)L] complex 1, based on the redox-active phenalenyl unit LH(2) = 9,9′-(ethane-1,2-diylbis(azanediyl))bis(1H-phenalen-1-one), is prepared and structurally characterized by single-crystal X-ray diffraction analysis. Complex 1 crystallizes at room temperature with the P1 space group. The molecular structure of 1 reveals the presence of intriguing C–H···Cu intermolecular anagostic interactions of the order ∼2.7715 Å. Utilizing the presence of anagostic interactions and the free nonbonding molecular orbitals (NBMOs) of the closed-shell phenalenyl unit in 1, the oxidation reactions of some industrially important polycyclic aromatic hydrocarbons (PAHs) in the presence of the [Cu(II)L] complex under very mild conditions have been reported. The direct conversion of anthracene-9-carbaldehyde to 9,10-anthraquinone in one step concludes that the catalyst shows dual activity in the chemical transformations. This also includes the first report of a “single-step” catalytic transformation of pyrene-1-carbaldehyde to the synthetically difficult pyren-4-ol, a precursor for the synthesis of several novel fluorescent probes for cell imaging. American Chemical Society 2022-03-01 /pmc/articles/PMC8928492/ /pubmed/35309439 http://dx.doi.org/10.1021/acsomega.1c07051 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/). |
spellingShingle | Kamboj, Nisha Mali, Ghanshyam Lama, Prem Erande, Rohan D. Metre, Ramesh K. Designing a Redox Noninnocent Phenalenyl-Based Copper(II) Complex: An Autotandem Catalyst for the Selective Oxidation of Polycyclic Aromatic Hydrocarbons (PAHs) |
title | Designing a Redox Noninnocent Phenalenyl-Based Copper(II)
Complex: An Autotandem Catalyst for the Selective Oxidation of Polycyclic
Aromatic Hydrocarbons (PAHs) |
title_full | Designing a Redox Noninnocent Phenalenyl-Based Copper(II)
Complex: An Autotandem Catalyst for the Selective Oxidation of Polycyclic
Aromatic Hydrocarbons (PAHs) |
title_fullStr | Designing a Redox Noninnocent Phenalenyl-Based Copper(II)
Complex: An Autotandem Catalyst for the Selective Oxidation of Polycyclic
Aromatic Hydrocarbons (PAHs) |
title_full_unstemmed | Designing a Redox Noninnocent Phenalenyl-Based Copper(II)
Complex: An Autotandem Catalyst for the Selective Oxidation of Polycyclic
Aromatic Hydrocarbons (PAHs) |
title_short | Designing a Redox Noninnocent Phenalenyl-Based Copper(II)
Complex: An Autotandem Catalyst for the Selective Oxidation of Polycyclic
Aromatic Hydrocarbons (PAHs) |
title_sort | designing a redox noninnocent phenalenyl-based copper(ii)
complex: an autotandem catalyst for the selective oxidation of polycyclic
aromatic hydrocarbons (pahs) |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8928492/ https://www.ncbi.nlm.nih.gov/pubmed/35309439 http://dx.doi.org/10.1021/acsomega.1c07051 |
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