Synthesis of Photochromic Oligophenylenimines: Optical and Computational Studies
Abstract
:1. Introduction
2. Results and Discussion
2.1. Synthesis
2.2. Optical Studies
2.2.1. Absorption Spectra in Different Solvents
SOLVENT | λmax/nm OIC1MS | ε × 104 (M−1 cm−1) OIC1MS | λmax/nm OIC2MS | ε × 104 (M−1 cm−1) OIC2MS |
---|---|---|---|---|
Toluene | 430 | 2.4 | 449 | 1.7 |
Chloroform | 430 | 2.3 | 425 | 3.2 |
Methanol | 434 | 1.7 | 425 | 1.5 |
Dichloromethane | 430 | 1.6 | 449 | 2 |
Tetrahydrofuran | 437 | 0.0982 | 440 | 1.1 |
2.2.2. Photochromic Properties
2.3. DFT Theoretical Studies
Wavelength (nm) | Oscillator Strength | Major Contributions |
---|---|---|
435.6 | 3.1 | H-1→L+1 (13%), HOMO→LUMO (73%) |
348.7 | 0.1 | H-2→LUMO (42%), H-1→L+1 (19%) |
298.5 | 0.3 | H-7→LUMO (16%) |
275.8 | 0.2 | H-2→LUMO (30%) |
221.1 | 0.2 | H-6→L+1 (16%), H-2→L+2 (22%) |
218.3 | 0.1 | H-6→L+1 (52%), H-2→L+2 (11%) |
215.2 | 0.1 | H-1→L+7 (25%), HOMO→L+7 (18%), HOMO→L+8 (14%) |
212.9 | 0.1 | H-3→L+2 (20%), HOMO→L+7 (16%) |
Wavelength (nm) | Oscillator Strength | Major Contributions |
---|---|---|
426.4 | 1.13 | H-2→LUMO (13%), H-1→L+1 (13%), HOMO→LUMO (44%) |
409.2 | 0.43 | H-2→LUMO (17%), H-1→LUMO (23%), HOMO→L+1 (26%) |
380.2 | 0.47 | H-2→LUMO (20%), H-1→L+1 (22%) |
371.0 | 0.53 | H-2→LUMO (16%), H-2→L+1 (40%) |
329.7 | 0.13 | H-4→LUMO (38%), H-3→L+1 (23%) |
300.0 | 0.23 | H-14→L+1 (10%), H-1→LUMO (14%) |
295.1 | 0.23 | H-17→LUMO (11%), H-15→LUMO (10%), H-1→LUMO (11%), H-1→L+1 (10%), HOMO→L+1 (12%) |
291.1 | 0.18 | H-2→LUMO (11%), H-1→LUMO (13%), H-1→L+1 (12%), HOMO→LUMO (18%) |
283.1 | 0.10 | H-1→L+1 (20%), HOMO→L+1 (25%) |
281.6 | 0.26 | H-1→L+6 (10%), HOMO→L+6 (15%) |
276.2 | 0.23 | H-1→L+6 (17%), HOMO→L+6 (14%) |
266.7 | 0.22 | H-1→L+3 (10%), HOMO→L+2 (15%), HOMO→L+3 (10%) |
261.7 | 0.28 | H-2→L+2 (25%) |
3. Experimental
3.1. General
3.2. Theoretical Calculations
3.3. Mechanosynthesis
Experimental Procedure
3.4. Conventional Synthesis
Experimental procedure
4. Conclusions
Supplementary Materials
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Pérez, A.I.M.; Alonso, O.C.; Borbolla, J.C.; Vásquez-Pérez, J.M.; Alonso, J.C.; Ayala, K.A.; Luna-Bárcenas, G.; Pandiyan, T.; García, R.A.V. Synthesis of Photochromic Oligophenylenimines: Optical and Computational Studies. Molecules 2015, 20, 5440-5455. https://doi.org/10.3390/molecules20045440
Pérez AIM, Alonso OC, Borbolla JC, Vásquez-Pérez JM, Alonso JC, Ayala KA, Luna-Bárcenas G, Pandiyan T, García RAV. Synthesis of Photochromic Oligophenylenimines: Optical and Computational Studies. Molecules. 2015; 20(4):5440-5455. https://doi.org/10.3390/molecules20045440
Chicago/Turabian StylePérez, Armando I. Martínez, Oscar Coreño Alonso, Julián Cruz Borbolla, José M. Vásquez-Pérez, Juan Coreño Alonso, Karina Alemán Ayala, Gabriel Luna-Bárcenas, Thangarasu Pandiyan, and Rosa A. Vázquez García. 2015. "Synthesis of Photochromic Oligophenylenimines: Optical and Computational Studies" Molecules 20, no. 4: 5440-5455. https://doi.org/10.3390/molecules20045440