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Large-Scale Green Synthesis of Porphyrins

[Image: see text] A new methodology for porphyrin synthesis has been developed. This is a simple two-step protocol. The first step involves the condensation of pyrrole and aldehyde in an H(2)O–MeOH mixture using HCl. The obtained precipitate from the first step was dissolved in reagent-grade dimethy...

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Autores principales: Mondal, Sruti, Pain, Tanmoy, Sahu, Kasturi, Kar, Sanjib
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8427785/
https://www.ncbi.nlm.nih.gov/pubmed/34514263
http://dx.doi.org/10.1021/acsomega.1c03534
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author Mondal, Sruti
Pain, Tanmoy
Sahu, Kasturi
Kar, Sanjib
author_facet Mondal, Sruti
Pain, Tanmoy
Sahu, Kasturi
Kar, Sanjib
author_sort Mondal, Sruti
collection PubMed
description [Image: see text] A new methodology for porphyrin synthesis has been developed. This is a simple two-step protocol. The first step involves the condensation of pyrrole and aldehyde in an H(2)O–MeOH mixture using HCl. The obtained precipitate from the first step was dissolved in reagent-grade dimethylformamide (DMF) and refluxed for 1.5 h, followed by stirring overnight in the air at room temperature. Subsequent purification through column chromatography or crystallization resulted in the formation of pure porphyrins. Advantageously, this methodology does not need any expensive chemicals such as 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ), chloranil, and so forth as an oxidizing agent. This reaction also does not require a large volume of dry chlorinated solvents. Contrary to the reported methodologies, which are mostly ineffective in the gram-scale production of porphyrins, the present method perfectly caters to the need for gram-scale production of porphyrins. In essence, the current methodology does not represent the synthesis having the highest yield in the literature. However, it represents the easiest and cheapest synthesis of porphyrin on a large scale to obtain a reproducible yield of 10–40% with high purity. In a few of the examples, even column chromatography is not necessary. A simple crystallization technique will be sufficient to generate the desired porphyrins in good yields.
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spelling pubmed-84277852021-09-10 Large-Scale Green Synthesis of Porphyrins Mondal, Sruti Pain, Tanmoy Sahu, Kasturi Kar, Sanjib ACS Omega [Image: see text] A new methodology for porphyrin synthesis has been developed. This is a simple two-step protocol. The first step involves the condensation of pyrrole and aldehyde in an H(2)O–MeOH mixture using HCl. The obtained precipitate from the first step was dissolved in reagent-grade dimethylformamide (DMF) and refluxed for 1.5 h, followed by stirring overnight in the air at room temperature. Subsequent purification through column chromatography or crystallization resulted in the formation of pure porphyrins. Advantageously, this methodology does not need any expensive chemicals such as 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ), chloranil, and so forth as an oxidizing agent. This reaction also does not require a large volume of dry chlorinated solvents. Contrary to the reported methodologies, which are mostly ineffective in the gram-scale production of porphyrins, the present method perfectly caters to the need for gram-scale production of porphyrins. In essence, the current methodology does not represent the synthesis having the highest yield in the literature. However, it represents the easiest and cheapest synthesis of porphyrin on a large scale to obtain a reproducible yield of 10–40% with high purity. In a few of the examples, even column chromatography is not necessary. A simple crystallization technique will be sufficient to generate the desired porphyrins in good yields. American Chemical Society 2021-08-24 /pmc/articles/PMC8427785/ /pubmed/34514263 http://dx.doi.org/10.1021/acsomega.1c03534 Text en © 2021 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 Mondal, Sruti
Pain, Tanmoy
Sahu, Kasturi
Kar, Sanjib
Large-Scale Green Synthesis of Porphyrins
title Large-Scale Green Synthesis of Porphyrins
title_full Large-Scale Green Synthesis of Porphyrins
title_fullStr Large-Scale Green Synthesis of Porphyrins
title_full_unstemmed Large-Scale Green Synthesis of Porphyrins
title_short Large-Scale Green Synthesis of Porphyrins
title_sort large-scale green synthesis of porphyrins
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8427785/
https://www.ncbi.nlm.nih.gov/pubmed/34514263
http://dx.doi.org/10.1021/acsomega.1c03534
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