Mono vs. Difunctional Coumarin as Photoinitiators in Photocomposite Synthesis and 3D Printing
Abstract
:1. Introduction
2. Results
2.1. Free Radical Photopolymerization (FRP) of Acrylate Monomers (TMPTA or Di(trimethylolpropane) Tetraacrylate (TA))
2.2. 3D-Printing Experiments Using Coum/Iod or Coum/Iod/4-N,N,TMA Systems
2.3. LED Conveyor Experiments for Composite Preparation
3. Discussion
3.1. Light Absorption Properties of the Different Dyes
3.2. (Photo)Chemical Mechanisms
3.2.1. Photophysical and Photochemical Properties of Coum3
3.2.2. Photophysical Properties of Coumarins Coum1 and Coum2
3.2.3. Fluorescence Quenching Experiments and Cyclic Voltammetry Measurements
3.2.4. Structure/Reactivity/Efficiency Relationship
4. Experimental Part
4.1. Synthesis of Coumarins
4.1.1. Synthesis of 7-(Diethylamino)-3-(thiophen-2-yl)-2H-chromen-2-one 3
4.1.2. Synthesis of 3-(5-Bromothiophen-2-yl)-7-(Diethylamino)-2H-chromen-2-one 4
4.1.3. Synthesis of 4-(5-(7-(Diethylamino)-2-oxo-2H-chromen-3-yl)thiophen-2-yl)benzaldehyde 5
4.1.4. Synthesis of 7-(Diethylamino)-3-(5-(4-(hydroxymethyl)phenyl)thiophen-2-yl)-2H-chromen-2-one Coum1
4.1.5. Synthesis of 4-(5-(7-(Diethylamino)-2-oxo-2H-chromen-3-yl) thiophen-2-yl) benzyl ethyl carbonate Coum2
4.1.6. Synthesis of bis (4-(5-(7-(Diethylamino)-2-oxo-2H-chromen-3-yl) thiophen-2-yl)benzyl)carbonate Coum3
4.2. Other Chemicals
4.3. Light Sources
4.4. Free Radical Photopolymerization (FRP)
4.5. Redox Potentials
4.6. Fluorescence Experiments
4.7. UV-Visible Absorption and Photolysis Experiments
4.8. Computational Procedure
4.9. 3D Printing Experiments
4.10. Near-UV Conveyor
5. Conclusions
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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Two-Component Photoinitiating System Coum/Iod (0.05%/1% w/w) and Coum/Iod (0.1%/1% w/w) | Three-Component Photoinitiating System Coum/Iod/EDB and Coum/Iod/NPG (0.1%/1%/1% w/w/w) | ||||
---|---|---|---|---|---|
Coum1/Iod 83% 1 73% 2 | Coum2/Iod 71% 1 83% 2 | Coum3/Iod n.p 1 32% 2 | Coum1/Iod/amine 84% 3 90% 4 | Coum2/Iod/amine 83% 3 89% 4 | Coum3/Iod/amine 59% 3 78% 4 |
- | λmax (nm) | εmax (M−1 cm−1) | ε@ 405 nm (M−1 cm−1) |
---|---|---|---|
Coum1 | 444 | 43,500 | 23,000 |
Coum2 | 444 | 69,900 | 35,900 |
Coum3 | 445 | 56,400 | 28,900 |
- | Eox (eV) | ES1 (eV) | ΔGS1 (eV) | KSV | ϕet(Coum/Iod) |
---|---|---|---|---|---|
Coum1 | 0.87 | 2.54 | −1.46 | 20 | 0.37 |
Coum2 | 0.86 | 2.56 | −1.49 | 93 | 0.87 |
Coum3 | n.o | 2.53 | - | 121 | 0.76 |
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Rahal, M.; Mokbel, H.; Graff, B.; Toufaily, J.; Hamieh, T.; Dumur, F.; Lalevée, J. Mono vs. Difunctional Coumarin as Photoinitiators in Photocomposite Synthesis and 3D Printing. Catalysts 2020, 10, 1202. https://doi.org/10.3390/catal10101202
Rahal M, Mokbel H, Graff B, Toufaily J, Hamieh T, Dumur F, Lalevée J. Mono vs. Difunctional Coumarin as Photoinitiators in Photocomposite Synthesis and 3D Printing. Catalysts. 2020; 10(10):1202. https://doi.org/10.3390/catal10101202
Chicago/Turabian StyleRahal, Mahmoud, Haifaa Mokbel, Bernadette Graff, Joumana Toufaily, Tayssir Hamieh, Frédéric Dumur, and Jacques Lalevée. 2020. "Mono vs. Difunctional Coumarin as Photoinitiators in Photocomposite Synthesis and 3D Printing" Catalysts 10, no. 10: 1202. https://doi.org/10.3390/catal10101202