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Open AccessArticle

Development of New High-Performance Biphenyl and Terphenyl Derivatives as Versatile Photoredox Photoinitiating Systems and Their Applications in 3D Printing Photopolymerization Processes

1
Cracow University of Technology, Faculty of Chemical Engineering and Technology, Warszawska 24, 31–155 Cracow, Poland
2
Jagiellonian University, Faculty of Chemistry, Gronostajowa 2, 30–387 Cracow, Poland
3
Photo HiTech Ltd., Bobrzyńskiego 14, 30–348 Cracow, Poland
*
Author to whom correspondence should be addressed.
Catalysts 2019, 9(10), 827; https://doi.org/10.3390/catal9100827
Received: 2 September 2019 / Revised: 27 September 2019 / Accepted: 28 September 2019 / Published: 1 October 2019
(This article belongs to the Special Issue Recent Advances in Photoredox Catalysts)
Novel 2-amino-4-methyl-6-phenyl-benzene-1,3-dicarbonitrile derivatives were proposed as photosensitizes of iodonium salt for a highly effective bimolecular photoinitiating system upon soft irradiation conditions under long-wave ultraviolet (UV-A) and visible light. Remarkably, these structures are highly versatile, allowing access to photoinitiating systems for the free-radical polymerization of acrylates, the cationic photopolymerization of epoxides, glycidyl, and vinyl ethers, the synthesis of interpenetrated polymer networks (IPNs) and the thiol-ene photopolymerization processes. Excellent polymerization profiles for all of the monomers, along with the high final conversions, were obtained. The initiation mechanisms of these bimolecular systems based on the 2-amino-4-methyl-6-phenyl-benzene-1,3-dicarbonitrile derivatives were investigated using the real-time FT-IR technique, steady-state photolysis, fluorescence experiments, theoretical calculations of molecular orbitals, and electrochemical analysis. Moreover, the 2-amino-4-methyl-6-phenyl-benzene-1,3-dicarbonitrile derivatives were investigated as a type II free-radical photoinitiator with amine. It was confirmed that the 2-amino-4-methyl-6-phenyl-benzene-1,3-dicarbonitrile derivatives, in combination with different types of additives, e.g., amine as co-initiator or in the presence of onium salt, can act as a bimolecular photoinitiating system via the photo-reduction or photo-oxidation pathways, respectively. View Full-Text
Keywords: photo-reduction; photo-oxidation; cationic photopolymerization; free-radical photopolymerization; copolymerization; IPNs; 3D printing photo-reduction; photo-oxidation; cationic photopolymerization; free-radical photopolymerization; copolymerization; IPNs; 3D printing
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MDPI and ACS Style

Tomal, W.; Pilch, M.; Chachaj-Brekiesz, A.; Ortyl, J. Development of New High-Performance Biphenyl and Terphenyl Derivatives as Versatile Photoredox Photoinitiating Systems and Their Applications in 3D Printing Photopolymerization Processes. Catalysts 2019, 9, 827.

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