Tetra-Dentate Cycloaddition Catalysts for Rapid Photopolymerization Reactions

Natanel Jarach, Hanna Dodiuk*, Samuel Kenig, Shlomo Magdassi*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

[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/cm2), 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/cm2), and long UV light (395 nm), this unique complex opens new avenues for recycling three-dimensional printing products based on photopolymerization of cycloaddition reactions.

Original languageAmerican English
Pages (from-to)5359-5367
Number of pages9
JournalJournal of Organic Chemistry
Volume88
Issue number9
DOIs
StatePublished - 5 May 2023

Bibliographical note

Publisher Copyright:
© 2023 The Authors. Published by American Chemical Society.

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