TY - JOUR
T1 - Tetra-Dentate Cycloaddition Catalysts for Rapid Photopolymerization Reactions
AU - Jarach, Natanel
AU - Dodiuk, Hanna
AU - Kenig, Samuel
AU - Magdassi, Shlomo
N1 - Publisher Copyright:
© 2023 The Authors. Published by American Chemical Society.
PY - 2023/5/5
Y1 - 2023/5/5
N2 - [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.
AB - [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.
UR - http://www.scopus.com/inward/record.url?scp=85152654321&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.2c02941
DO - 10.1021/acs.joc.2c02941
M3 - ???researchoutput.researchoutputtypes.contributiontojournal.article???
C2 - 37029749
AN - SCOPUS:85152654321
SN - 0022-3263
VL - 88
SP - 5359
EP - 5367
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 9
ER -