Physico-Chemical and Light-Induced Properties of Quinoline Azo-dyes Polymers
Abstract
:1. Introduction
2. Results and Discussion
2.1. AFM Studies
2.2. TGA/DSC Studies
2.3. UV-VIS Measurements
2.4. Ellipsometric Studies
2.5. Photoisomerization Studies
2.6. Holographic Grating Inscription
3. Materials and Methods
3.1. Materials and Synthesis
3.1.1. Polymerization
3.1.2. Density Functional Theory Geometry Optimization
3.2. Sample Preparation
3.3. Material Characterization
3.3.1. NMR and Mass Spectra
3.3.2. Thermal Measurements
3.3.3. Atomic Force Microscope
3.3.4. UV-Vis Spectra
3.3.5. Ellipsometry Measurements
3.3.6. Light-Responsive Behavior Measurements
3.3.7. Holographic Grating Inscription
4. Conclusions
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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Irradiation | qA-N(CH3)2 | qA-OCH3 | qA-CH3 | qA-H | qA-Br | qA-COOH | qA-CF3 | |
---|---|---|---|---|---|---|---|---|
Ra (nm) | before | 0.39 | 0.58 | 0.36 | 1.36 | 0.33 | 1.40 | 0.39 |
after | 0.24 | 0.28 | 0.44 | 1.46 | 0.37 | 7.11 | 0.25 | |
Rq (nm) | before | 0.49 | 0.86 | 0.56 | 1.76 | 0.43 | 1.88 | 0.72 |
after | 0.34 | 0.38 | 0.53 | 1.96 | 0.50 | 8.95 | 0.54 | |
L (nm) | 672 ± 2 | 680 ± 5 | 621 ± 2 | 485 ± 1 | 499 ± 2 | 368 ± 3 | 558 ± 1 |
Parameters | PMMA | qA-N(CH3)2 | qA-OCH3 | qA-CH3 | qA-H | qA-Br | qA-COOH | qA-CF3 |
---|---|---|---|---|---|---|---|---|
T1max (°C) | 275 | 292 | 311 | 296 | 188 | 302 | 156 | 305 |
Δm1 (%) | 41.5 | 32.6 | 24.0 | 25.4 | 7.0 | 24.6 | 9.4 | 29.0 |
T2max (°C) | 385 | 400 | 389 | 370 | 304 | 404 | 306 | 381 |
Δm2 (%) | 58.5 | 38.1 | 57.3 | 51.8 | 21.0 | 46.8 | 17.6 | 46.7 |
T3max (°C) | - | - | - | - | 387 | - | 409 | - |
Δm3 (%) | - | - | - | - | 46.8 | - | 44.3 | - |
Char yield (%) at 600 °C | 0 | 24.4 | 13.7 | 18.7 | 17.8 | 21.8 | 25.5 | 21.6 |
Energies | qA-N(CH3)2 | qA-OCH3 | qA-CH3 | qA-H | qA-Br | qA-COOH | qA-CF3 | |
---|---|---|---|---|---|---|---|---|
Eg | (eV) (nm) | 2.34 ± 0.05 530 ± 11 | 2.96 ± 0.05 419 ± 7 | 3.02 ± 0.06 411 ± 8 | 3.05 ± 0.05 407 ± 10 | 2.98 ± 0.05 416 ± 7 | 2.99 ± 0.05 415 ± 7 | 3.04 ± 0.07 408 ± 9 |
E1 | (eV) (nm) | 2.48 ± 0.01 499 ± 2 | 3.21 ± 0.03 386 ± 4 | 2.64 ± 0.03 470 ± 6 | 2.74 ± 0.02 453 ± 3 | 2.68 ± 0.11 463 ± 19 | 3.19 ± 0.04 389 ± 5 | 2.71 ± 0.02 458 ± 4 |
E2 | (eV) (nm) | 2.69 ± 0.03 460 ± 6 | 3.38 ± 7.74 367 ± 200 | 3.13 ± 0.02 396 ± 3 | 3.15 ± 0.01 394 ± 2 | 3.10 ± 0.02 400 ± 3 | 3.38 ± 0.03 367 ± 3 | 3.18 ± 0.01 390 ± 1 |
E3 | (eV) (nm) | 2.87 ± 0.03 432 ± 5 | 3.38 ± 0.04 367 ± 4 | 3.35 ± 0.03 370 ± 3 | 3.62 ± 0.03 343 ± 3 | 3.33 ± 0.03 372 ± 4 | 4.00 ± 0.27 310 ± 22 | 3.38 ± 0.04 367 ± 4 |
E4 | (eV) (nm) | 3.55 ± 0.22 349 ± 23 | 3.63 ± 0.12 342 ± 11 | 3.61 ± 0.04 343 ± 4 | 4.27 ± 0.03 290 ± 2 | 3.66 ± 0.10 339 ± 9 | 4.90 ± 0.12 253 ± 6 | 3.44 ± 0.04 360 ± 5 |
E5 | (eV) (nm) | 3.84 ± 0.06 323 ± 5 | 4.75 ± 0.05 261 ± 3 | 3.69 ± 0.12 336 ± 11 | 3.69 ± 0.04 336 ± 4 | |||
E6 | (eV) (nm) | 4.78 ± 0.09 259 ± 5 |
qA-N(CH3)2 | qA-OCH3 | qA-CH3 | qA-H | qA-Br | qA-COOH | qA-CF3 | |
---|---|---|---|---|---|---|---|
Decay time τ (s) | - | 38.7 ± 0.9 | 58.58 ± 0.71 | 58.9 ± 1.4 | 55.3 ± 2.6 | 50.2 ± 1.1 | 71.0 ± 3.4 |
Isomerization rate p (s−1) | - | (25.9 ± 0.6) × 10−3 | (17.07 ± 0.21) × 10−3 | (16.97 ± 0.41) × 10−3 | (18.09 ± 0.83) × 10−3 | (19.92 ± 0.42) × 10−3 | (14.1 ± 0.7) × 10−3 |
Isosbestic points (nm) | - | 329 | 310 | 306 | 311 | 312 | 303 |
453 | 427 | 421 | 433 | 426 | 425 |
qA-N(CH3)2 | qA-OCH3 | qA-CH3 | qA-H | qA-Br | qA-COOH | qA-CF3 | |
---|---|---|---|---|---|---|---|
Types of substituents | electron donating group | neutral | electron withdrawing group | ||||
R | N(CH3)2 | OCH3 | CH3 | H | Br | COOH | CF3 |
R’s Hammett sigma constant | −0.83 | −0.27 | -0.17 | 0 | 0.23 | 0.45 | 0.54 |
Dipole moment (Debye) | 6.5 | 3.0 | 2.3 | 1.7 | 1.9 | 6.2 | 3.6 |
qA-N(CH3)2 | qA-OCH3 | qA-CH3 | qA-H | qA-Br | qA-COOH | qA-CF3 | |
---|---|---|---|---|---|---|---|
Initial monomers mole ratio n/m | 1:3 | ||||||
ratio n/m a | 1:3.1 | 1:3.0 | 1:3.2 | 1:3.2 | 1:3.1 | 1:3.1 | 1:2.9 |
Mwb (g/mol) | 24800 | 36000 | 28100 | 25500 | 32000 | 25000 | 33200 |
Mw/Mn b | 1.7 | 2.0 | 1.9 | 1.8 | 1.9 | 1.83 | 1.61 |
Tg c (°C) | - | 121 | 122 | 135 | 94 | 129 | 128 |
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Chomicki, D.; Kharchenko, O.; Skowronski, L.; Kowalonek, J.; Kozanecka-Szmigiel, A.; Szmigiel, D.; Smokal, V.; Krupka, O.; Derkowska-Zielinska, B. Physico-Chemical and Light-Induced Properties of Quinoline Azo-dyes Polymers. Int. J. Mol. Sci. 2020, 21, 5755. https://doi.org/10.3390/ijms21165755
Chomicki D, Kharchenko O, Skowronski L, Kowalonek J, Kozanecka-Szmigiel A, Szmigiel D, Smokal V, Krupka O, Derkowska-Zielinska B. Physico-Chemical and Light-Induced Properties of Quinoline Azo-dyes Polymers. International Journal of Molecular Sciences. 2020; 21(16):5755. https://doi.org/10.3390/ijms21165755
Chicago/Turabian StyleChomicki, Dariusz, Oksana Kharchenko, Lukasz Skowronski, Jolanta Kowalonek, Anna Kozanecka-Szmigiel, Dariusz Szmigiel, Vitalii Smokal, Oksana Krupka, and Beata Derkowska-Zielinska. 2020. "Physico-Chemical and Light-Induced Properties of Quinoline Azo-dyes Polymers" International Journal of Molecular Sciences 21, no. 16: 5755. https://doi.org/10.3390/ijms21165755