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Preparations of Core H(2)O-Bound 5, 10, 15, 20-Tetrakis-4-chlorophenyl Porphyrin, P(1), and O-Methylation of Phenol and Its P-Substituted Analogues

[Image: see text] The treatment of a dichloromethane solution of 5, 10, 15, 20-tetrakis-4-chlorophenyl porphyrin, P(1), with methanolic solutions of each of phenol, p-amino phenol, and p-nitro phenol for just 1 h results in the formation of water-molecule-bound amorphous solids of P(1). In addition...

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Autores principales: Dechan, Padma, Bajju, Gauri Devi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7377681/
https://www.ncbi.nlm.nih.gov/pubmed/32715264
http://dx.doi.org/10.1021/acsomega.0c02449
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author Dechan, Padma
Bajju, Gauri Devi
author_facet Dechan, Padma
Bajju, Gauri Devi
author_sort Dechan, Padma
collection PubMed
description [Image: see text] The treatment of a dichloromethane solution of 5, 10, 15, 20-tetrakis-4-chlorophenyl porphyrin, P(1), with methanolic solutions of each of phenol, p-amino phenol, and p-nitro phenol for just 1 h results in the formation of water-molecule-bound amorphous solids of P(1). In addition to the straightforward access to the H(2)O-molecule-coordinated species of P(1) thus produced, the another chief advantage of this synthetic strategy is the successful recoveries of anisole, p-amino anisole, and p-nitro anisole at the end of the reactions. The present work therefore further reports the use of P(1) as an efficient catalyst for the selective O-methylation of phenols using methanol as an environmentally friendly methylating agent. The H(2)O-bound amorphous solids of P(1) exhibit higher-intensity absorption as well as photoluminescence emission bands in dichloromethane compared with the parent crystalline form. Further, the measurement of the solid-state emission properties of both the crystalline and amorphous forms indicates quenching of fluorescence bands corresponding to amorphous solids in comparison with that of parent crystalline form. The crystalline form of P(1) and the H(2)O-bound amorphous solids were further studied by scanning electron microscope/transmission electron microscope (SEM/TEM), powder X-ray diffraction (XRD), Brunauer–Emmett–Teller (BET), and thermal analysis techniques. The results of these studies indicate change in morphological and structural features, surface areas, porosities, and thermal robustness upon core coordination of water molecules with the macrocyclic rings of P(1).
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spelling pubmed-73776812020-07-24 Preparations of Core H(2)O-Bound 5, 10, 15, 20-Tetrakis-4-chlorophenyl Porphyrin, P(1), and O-Methylation of Phenol and Its P-Substituted Analogues Dechan, Padma Bajju, Gauri Devi ACS Omega [Image: see text] The treatment of a dichloromethane solution of 5, 10, 15, 20-tetrakis-4-chlorophenyl porphyrin, P(1), with methanolic solutions of each of phenol, p-amino phenol, and p-nitro phenol for just 1 h results in the formation of water-molecule-bound amorphous solids of P(1). In addition to the straightforward access to the H(2)O-molecule-coordinated species of P(1) thus produced, the another chief advantage of this synthetic strategy is the successful recoveries of anisole, p-amino anisole, and p-nitro anisole at the end of the reactions. The present work therefore further reports the use of P(1) as an efficient catalyst for the selective O-methylation of phenols using methanol as an environmentally friendly methylating agent. The H(2)O-bound amorphous solids of P(1) exhibit higher-intensity absorption as well as photoluminescence emission bands in dichloromethane compared with the parent crystalline form. Further, the measurement of the solid-state emission properties of both the crystalline and amorphous forms indicates quenching of fluorescence bands corresponding to amorphous solids in comparison with that of parent crystalline form. The crystalline form of P(1) and the H(2)O-bound amorphous solids were further studied by scanning electron microscope/transmission electron microscope (SEM/TEM), powder X-ray diffraction (XRD), Brunauer–Emmett–Teller (BET), and thermal analysis techniques. The results of these studies indicate change in morphological and structural features, surface areas, porosities, and thermal robustness upon core coordination of water molecules with the macrocyclic rings of P(1). American Chemical Society 2020-07-12 /pmc/articles/PMC7377681/ /pubmed/32715264 http://dx.doi.org/10.1021/acsomega.0c02449 Text en Copyright © 2020 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 Dechan, Padma
Bajju, Gauri Devi
Preparations of Core H(2)O-Bound 5, 10, 15, 20-Tetrakis-4-chlorophenyl Porphyrin, P(1), and O-Methylation of Phenol and Its P-Substituted Analogues
title Preparations of Core H(2)O-Bound 5, 10, 15, 20-Tetrakis-4-chlorophenyl Porphyrin, P(1), and O-Methylation of Phenol and Its P-Substituted Analogues
title_full Preparations of Core H(2)O-Bound 5, 10, 15, 20-Tetrakis-4-chlorophenyl Porphyrin, P(1), and O-Methylation of Phenol and Its P-Substituted Analogues
title_fullStr Preparations of Core H(2)O-Bound 5, 10, 15, 20-Tetrakis-4-chlorophenyl Porphyrin, P(1), and O-Methylation of Phenol and Its P-Substituted Analogues
title_full_unstemmed Preparations of Core H(2)O-Bound 5, 10, 15, 20-Tetrakis-4-chlorophenyl Porphyrin, P(1), and O-Methylation of Phenol and Its P-Substituted Analogues
title_short Preparations of Core H(2)O-Bound 5, 10, 15, 20-Tetrakis-4-chlorophenyl Porphyrin, P(1), and O-Methylation of Phenol and Its P-Substituted Analogues
title_sort preparations of core h(2)o-bound 5, 10, 15, 20-tetrakis-4-chlorophenyl porphyrin, p(1), and o-methylation of phenol and its p-substituted analogues
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7377681/
https://www.ncbi.nlm.nih.gov/pubmed/32715264
http://dx.doi.org/10.1021/acsomega.0c02449
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