One-component cationic photoinitiators from tunable benzylidene scaffolds for 3D printing applications
Authors:
- Filip Petko,
- Mariusz Galek,
- Emilia Hola,
- Roman Popielarz,
- Joanna Ortyl
Abstract
This paper describes a series of novel benzylidene scaffold-based iodonium salt one-component photoinitiators containing double bonds and dialkylamino groups synthesized in one step via classical aldol condensation reactions. Systematic investigations of structure−activity relationships were performed via quantum-chemical calculations and experimental tests. New salts can efficiently decompose under irradiation from UV to visible regions of the spectrum. The design of new iodonium salts is described, followed by a description of properties of photoinitiators prepared in this way. All presented salts were characterized in terms of their spectral properties (UV−vis spectroscopy), ability to photodecompose (steady-state photolysis), cationic polymerization of the vinyl monomer, and epoxide monomer photoinitiation (quantum efficiency of acid generation and real-time Fourier-transform infrared measurements) as well as their proposed application in 3D printing. New benzylidene iodonium salts can photoinitiate the polymerization of vinyl ethers and epoxy monomers under LED@365 and LED@405 irradiation. Investigated compounds can simultaneously initiate and monitor the polymerization process according to the change of fluorescence during the photocuring process. Formulations before photopolymerization do not exhibit fluorescence, during the photopolymerization process fluorescence is “turning on”. This phenomenon might be used to monitor photopolymerization in an “online” manner.
- Record ID
- CUTcfb5ed08c0e64c1e8c895797585ef931
- Publication categories
- ;
- Author
- Journal series
- Macromolecules, ISSN 0024-9297, e-ISSN 1520-5835
- Issue year
- 2021
- Vol
- 54
- No
- 15
- Pages
- 7070-7087
- Other elements of collation
- schem.; tab.; wykr.; Bibliografia (na s.) - 7086-7087; Bibliografia (liczba pozycji) - 44; Oznaczenie streszczenia - Abstr.; Numeracja w czasopiśmie - Vol. 54, Iss. 15
- Keywords in English
- salts, photopolymerization, reaction products, absorption, chromophores
- DOI
- DOI:10.1021/acs.macromol.1c01048 Opening in a new tab
- URL
- https://pubs.acs.org/doi/10.1021/acs.macromol.1c01048 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] - Molecular desing, synthesis and application of photoinitiator-catalysts (PICs) for photopolymerization reactions. . Project leader at PK: , ,
- Synthesis and photochemistry/photophysics studies of the intelligent luminescent molecular sensors for selective detection in biochemistry and chemistry. . Project leader at PK: , ,
- 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)
- 140
- Additional fields
- Indeksowana w: Web of Science, Scopus
- Uniform Resource Identifier
- https://cris.pk.edu.pl/info/article/CUTcfb5ed08c0e64c1e8c895797585ef931/
- URN
urn:pkr-prod:CUTcfb5ed08c0e64c1e8c895797585ef931
* 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.