Development of new high-performance biphenyl and terphenyl derivatives as versatile photoredox photoinitiating systems and their applications in 3D printing photopolymerization processes
Authors:
- Wiktoria Tomal,
- Maciej Pilch,
- Anna Chachaj-Brekiesz,
- Joanna Ortyl
Abstract
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.
- Record ID
- CUT1a03026a1d244e4da87a60cacc83245b
- Publication categories
- ;
- Author
- Journal series
- Catalysts, ISSN , e-ISSN 2073-4344, Monthly
- Issue year
- 2019
- Vol
- 9
- No
- 10
- Pages
- [1-27]
- Article number
- 827
- Other elements of collation
- fot.; rys.; schem.; tab.; wykr.; Bibliografia (na s.) - 25-27; Bibliografia (liczba pozycji) - 53; Oznaczenie streszczenia - Abstr.; Numeracja w czasopiśmie - Vol. 9, Iss. 10, Spec. Iss.
- Substantive notes
- Special Issue: Recent Advances in Photoredox Catalysts
- Keywords in English
- photo-reduction, photo-oxidation, cationic photopolymerization, free-radical photopolymerization, copolymerization, IPNs, 3D printing
- DOI
- DOI:10.3390/catal9100827 Opening in a new tab
- URL
- https://www.mdpi.com/2073-4344/9/10/827 Opening in a new tab
- Related project
- Synteza bimolekularnych fotoinicjatorów kationowych i badania mechanistycznych aspektów fotogenerowania mocnych kwasów protonowych w procesach synergistycznego oddziaływania soli oniowych oraz fotosensybilizatorów lub koinicjatorów. . Project leader at PK: , ,
Projects financed by NSC [Projekty finansowane przez NCN] - Implementacja fotogeneratorów mocnych kwasów protonowych (PAG-s) opartych o innowacyjne molekuły akcelerujące do aplikacji w przemyśle fotoutwardzalnych powłok polimerowych. . Project leader at PK: , ,
Projects financed by NCRD [Projekty finansowane przez NCBiR (NCBR (]
- Synteza bimolekularnych fotoinicjatorów kationowych i badania mechanistycznych aspektów fotogenerowania mocnych kwasów protonowych w procesach synergistycznego oddziaływania soli oniowych oraz fotosensybilizatorów lub koinicjatorów. . Project leader at PK: , ,
- Language
- eng (en) English
- License
- Score (nominal)
- 100
- Additional fields
- Indeksowana w: Web of Science, Scopus
- Uniform Resource Identifier
- https://cris.pk.edu.pl/info/article/CUT1a03026a1d244e4da87a60cacc83245b/
- URN
urn:pkr-prod:CUT1a03026a1d244e4da87a60cacc83245b
* presented citation count is obtained through Internet information analysis, and it is close to the number calculated by the Publish or PerishOpening in a new tab system.