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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...

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Autores principales: Jarach, Natanel, Dodiuk, Hanna, Kenig, Samuel, Magdassi, Shlomo
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
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.
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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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