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Tetra-Dentate Cycloaddition Catalysts for Rapid Photopolymerization Reactions
[Image: see text] [4 + 4] and [2 + 2] cycloadditions are unique reactions since they form and deform cycloadducts under irradiation due to their inherent reversible nature. Whereas promising for the field of recycling, these reactions usually suffer from two major shortcomings: long reaction duratio...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2023
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10167662/ https://www.ncbi.nlm.nih.gov/pubmed/37029749 http://dx.doi.org/10.1021/acs.joc.2c02941 |
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author | Jarach, Natanel Dodiuk, Hanna Kenig, Samuel Magdassi, Shlomo |
author_facet | Jarach, Natanel Dodiuk, Hanna Kenig, Samuel Magdassi, Shlomo |
author_sort | Jarach, Natanel |
collection | PubMed |
description | [Image: see text] [4 + 4] and [2 + 2] cycloadditions are unique reactions since they form and deform cycloadducts under irradiation due to their inherent reversible nature. Whereas promising for the field of recycling, these reactions usually suffer from two major shortcomings: long reaction durations (hours) and the requirement of high-intensity light (∼100 W/cm(2)), typically at a short wavelength (<330 nm). We demonstrate several tetra-dentate catalysts that can overcome these fundamental limitations. Among them is a tin complex that enables 76% conversion within only 2 min of irradiation at 395 nm, much faster than the known ruthenium-based catalyst, under irradiation with light intensity two orders of magnitude lower than that reported in the literature. Due to the short photopolymerization time, low intensity (27 mW/cm(2)), and long UV light (395 nm), this unique complex opens new avenues for recycling three-dimensional printing products based on photopolymerization of cycloaddition reactions. |
format | Online Article Text |
id | pubmed-10167662 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-101676622023-05-10 Tetra-Dentate Cycloaddition Catalysts for Rapid Photopolymerization Reactions Jarach, Natanel Dodiuk, Hanna Kenig, Samuel Magdassi, Shlomo J Org Chem [Image: see text] [4 + 4] and [2 + 2] cycloadditions are unique reactions since they form and deform cycloadducts under irradiation due to their inherent reversible nature. Whereas promising for the field of recycling, these reactions usually suffer from two major shortcomings: long reaction durations (hours) and the requirement of high-intensity light (∼100 W/cm(2)), typically at a short wavelength (<330 nm). We demonstrate several tetra-dentate catalysts that can overcome these fundamental limitations. Among them is a tin complex that enables 76% conversion within only 2 min of irradiation at 395 nm, much faster than the known ruthenium-based catalyst, under irradiation with light intensity two orders of magnitude lower than that reported in the literature. Due to the short photopolymerization time, low intensity (27 mW/cm(2)), and long UV light (395 nm), this unique complex opens new avenues for recycling three-dimensional printing products based on photopolymerization of cycloaddition reactions. American Chemical Society 2023-04-08 /pmc/articles/PMC10167662/ /pubmed/37029749 http://dx.doi.org/10.1021/acs.joc.2c02941 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Jarach, Natanel Dodiuk, Hanna Kenig, Samuel Magdassi, Shlomo Tetra-Dentate Cycloaddition Catalysts for Rapid Photopolymerization Reactions |
title | Tetra-Dentate Cycloaddition
Catalysts for Rapid Photopolymerization
Reactions |
title_full | Tetra-Dentate Cycloaddition
Catalysts for Rapid Photopolymerization
Reactions |
title_fullStr | Tetra-Dentate Cycloaddition
Catalysts for Rapid Photopolymerization
Reactions |
title_full_unstemmed | Tetra-Dentate Cycloaddition
Catalysts for Rapid Photopolymerization
Reactions |
title_short | Tetra-Dentate Cycloaddition
Catalysts for Rapid Photopolymerization
Reactions |
title_sort | tetra-dentate cycloaddition
catalysts for rapid photopolymerization
reactions |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10167662/ https://www.ncbi.nlm.nih.gov/pubmed/37029749 http://dx.doi.org/10.1021/acs.joc.2c02941 |
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