Coumarins as Powerful Photosensitizers for the Cationic Polymerization of Epoxy-Silicones under Near-UV and Visible Light and Applications for 3D Printing Technology
Abstract
:1. Introduction
2. Results and Discussion
2.1. Synthesis of Coumarins
2.2. Light Absorption Properties of the Examined Coumarins
2.3. Cationic Photopolymerization (CP) of Epoxy-Silicones
2.4. 3D Patterns in the Presence of Coumarin/IOD Couples
3. Materials and Methods
3.1. Synthesis of the Coumarins Investigated in This Research
3.2. Commercial Chemical Compounds Used in This Study
3.3. Light Irradiation Sources
3.4. Cationic Photopolymerization (CP) Followed by Real-Time Fourier Transform InfraRed Spectroscopy (RT-FTIR)
3.5. Redox Potentials
3.6. UV-Visible Absorption Experiments
3.7. Fluorescence Experiments
3.8. 3D Printing Experiments
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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Sample Availability: Samples of the compounds are not available from the authors. |
PI | λmax (nm) | εmax (M−1. cm−1) | ε@405 nm (M−1. cm−1) |
---|---|---|---|
Coumarin 1 | 411 | 48630 | 47950 |
Coumarin 2 | 407 | 42360 | 42270 |
Coumarin 3 | 421 | 35200 | 30600 |
Coumarin 4 | 408 | 23530 | 23340 |
Coumarin 5 | 445 | 34380 | 16880 |
Coumarin 6 | 361 | 22970 | 6080 |
Coumarin 7 | 357 | 9210 | 530 |
Coumarin 8 | 342 | 24760 | 260 |
Com. Coum 1 | 299 | 11150 | 40 |
Com. Coum 2 | 457 | 58640 | 17450 |
Com. Coum 3 | 324 | 11310 | 40 |
Com. Coum 4 | 368 | 18200 | 1100 |
Coumarin 1 | Coumarin 2 | Coumarin 3 | Coumarin 4 | Coumarin 5 | Coumarin 6 | Coumarin 7 | Coumarin 8 | Com. Coum 2 | Com. Coum 4 | CPTX | DBA |
---|---|---|---|---|---|---|---|---|---|---|---|
57% a | 55% a | 55% a | 53% a | 47% a | 52% a | 57% a | 59% a | 47% a | 52% a | 48% b | 55% b |
55% b | 55% b | 55% b | 54% b | 44% b | 52% b | 57% b | 60% b | 47% b | 55% b |
PI | ES1 (eV) | ET1 (eV)a | Eox (eV) | ΔGet(S1)b(PI/Iod) (eV) | ΔGet(T1)b(PI/Iod) (eV) |
---|---|---|---|---|---|
Coumarin 1 | 2.7 | 1.94 | 1.03 | −1.47 | −0.71 |
Coumarin 2 | 2.74 | 1.99 | 0.95 | −1.59 | −0.84 |
Coumarin 3 | 2.68 | 1.81 | 0.81 | −1.67 | −0.8 |
Coumarin 4 | 2.74 | 2.04 | 0.35 | −2.19 | −1.49 |
Coumarin 5 | 2.55 | 1.67 | 0.45 | −1.9 | −1.02 |
Coumarin 6 | 3.02 | 1.91 | 0.47 | −2.35 | −1.24 |
Coumarin 7 | 2.69 | 1.81 | 1.12 | −1.37 | −0.49 |
Coumarin 8 | 3.22 | 2.19 | 0.45 | −2.57 | −1.54 |
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Abdallah, M.; Hijazi, A.; Dumur, F.; Lalevée, J. Coumarins as Powerful Photosensitizers for the Cationic Polymerization of Epoxy-Silicones under Near-UV and Visible Light and Applications for 3D Printing Technology. Molecules 2020, 25, 2063. https://doi.org/10.3390/molecules25092063
Abdallah M, Hijazi A, Dumur F, Lalevée J. Coumarins as Powerful Photosensitizers for the Cationic Polymerization of Epoxy-Silicones under Near-UV and Visible Light and Applications for 3D Printing Technology. Molecules. 2020; 25(9):2063. https://doi.org/10.3390/molecules25092063
Chicago/Turabian StyleAbdallah, Mira, Akram Hijazi, Frédéric Dumur, and Jacques Lalevée. 2020. "Coumarins as Powerful Photosensitizers for the Cationic Polymerization of Epoxy-Silicones under Near-UV and Visible Light and Applications for 3D Printing Technology" Molecules 25, no. 9: 2063. https://doi.org/10.3390/molecules25092063