Microwave-Assisted Synthesis, Optical and Theoretical Characterization of Novel 2-(imidazo[1,5-a]pyridine-1-yl)pyridinium Salts
Abstract
:1. Introduction
2. Materials and Methods
2.1. Synthesis
2.1.1. Synthesis of 3-phenyl-1-(pyridin-2-yl)imidazo[1,5-a]pyridine (1)
2.1.2. Synthesis of 1,4-bis(1-(pyridin-2-yl)imidazo[1,5-a]pyridin-3-yl)benzene (2)
2.1.3. Synthesis of 1,3-bis(1-(pyridin-2-yl)imidazo[1,5-a]pyridin-3-yl)benzene (3)
2.1.4. Synthesis of 1-ethyl-2-(3-phenylImidazo[1,5-a]pyridine-1-yl)pyridine-1-ium Iodide (1q)
2.1.5. Synthesis of 2,2′-(3,3′-(1,4-phenylene)bis(imidazo[1,5-a]pyridine-3,1-diyl))bis(1-ethylpyridin-1-ium iodide (2q)
2.1.6. Synthesis of 2,2′-(3,3′-(1,3-phenylene)bis(imidazo[1,5-a]pyridine-3,1-diyl))bis(1-ethylpyridin-1-ium) iodide (3q)
2.2. Photophysical Properties
2.3. Computational Details
3. Results and Discussion
3.1. Note about the Synthesis
3.2. Notes about the Photophysical Properties
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
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Compound | λabs/nm | λem/nm | Δλem-abs/nm | ϕ/% | <τ>/ns | krad 107/s−1 | knrad 107/s−1 |
---|---|---|---|---|---|---|---|
1 | 323 | 463 | 140 | 22 | 6.03 | 3.65 | 12.9 |
1q | 302/426 | 551 | 125 | <5 | 2.89 | 1.73 | 32.9 |
2 | 332/378 | 470 | 92 | 22 | 6.27 | 3.51 | 12.4 |
2q | 303/353/425 | 524 | 99 | <5 | 3.15 | 1.59 | 30.2 |
3 | 329 | 461 | 132 | 19 | 5.76 | 3.30 | 14.1 |
3q | 316/430 | 515 | 85 | <5 | 3.3 | 1.52 | 28.8 |
Compound | Conditions | λem/nm | ϕ/% (λex/nm) | <τ>/ns | krad 107/s−1 | knrad 107/s−1 |
---|---|---|---|---|---|---|
1 | Solution | 463 | 22 (325) | 6.03 | 3.65 | 12.9 |
Thin film | 613 | <5 (330) | 3.02 | 1.66 | 31.5 | |
25% PMMA | 610 | <5 (330) | 1.96 | 2.55 | 48.5 | |
40% PMMA | 507 | <5 (330) | 2.3 | 2.17 | 41.3 | |
75% PMMA | 525 | <5 (330) | 2.23 | 2.24 | 42.6 | |
25% PS | 612 | <5 (330) | 1.42 | 3.52 | 66.9 | |
40% PS | 505 | <5 (330) | 1.93 | 2.59 | 49.2 | |
75% PS | 502 | <5 (330) | 2.4 | 2.08 | 39.6 | |
1q | Solution | 550 | <5 (420) | 2.89 | 1.73 | 32.9 |
Thin film | 635 | <5 (420) | 1.87 | 2.67 | 50.8 | |
25% PS | 635 | <5 (420) | 1.4 | 3.57 | 67.9 | |
40% PS | 635 | <5 (420) | 1.17 | 4.27 | 81.2 | |
75% PS | 635 | <5 (420) | 1.36 | 3.68 | 69.9 |
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Cavinato, L.M.; Volpi, G.; Fresta, E.; Garino, C.; Fin, A.; Barolo, C. Microwave-Assisted Synthesis, Optical and Theoretical Characterization of Novel 2-(imidazo[1,5-a]pyridine-1-yl)pyridinium Salts. Chemistry 2021, 3, 714-727. https://0-doi-org.brum.beds.ac.uk/10.3390/chemistry3030050
Cavinato LM, Volpi G, Fresta E, Garino C, Fin A, Barolo C. Microwave-Assisted Synthesis, Optical and Theoretical Characterization of Novel 2-(imidazo[1,5-a]pyridine-1-yl)pyridinium Salts. Chemistry. 2021; 3(3):714-727. https://0-doi-org.brum.beds.ac.uk/10.3390/chemistry3030050
Chicago/Turabian StyleCavinato, Luca M., Giorgio Volpi, Elisa Fresta, Claudio Garino, Andrea Fin, and Claudia Barolo. 2021. "Microwave-Assisted Synthesis, Optical and Theoretical Characterization of Novel 2-(imidazo[1,5-a]pyridine-1-yl)pyridinium Salts" Chemistry 3, no. 3: 714-727. https://0-doi-org.brum.beds.ac.uk/10.3390/chemistry3030050