2,1,3-Benzothiadiazole Small Donor Molecules: A DFT Study, Synthesis, and Optoelectronic Properties
Abstract
:1. Introduction
2. Results
2.1. Synthesis
2.2. Theoretical Studies
2.3. Photophysical Studies
2.4. Electrochemical Properties
3. Materials and Methods
3.1. Computational Details
3.2. Chemistry
3.2.1. Preparation of 4,7-bis(5-(selenophen-2-yl)thiophen-2-yl)benzothiadiazole (2a)
3.2.2. Preparation of 4,7-bis(5-(pyridin-2-yl)thiophen-2-yl)benzothiadiazole (2b)
3.2.3. Preparation of 4,7-bis(5-(3,4-ethylenedioxythiophene)thiophen-2-yl)benzothiadiazole (2c)
3.2.4. Preparation of 4,7-di([2,2′-bithiophen]-5-yl)benzothiadiazole (2d)
3.3. Optical Measurements
3.4. Cyclic Voltammetry
4. Conclusions
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
Sample Availability
References
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Compound | Eoxonset (V) | Eredonset (V) | IP (eV) | IPvercal (eV) | IPadcal (eV) | EA (eV) | HOMOcal (eV) | LUMOcal (eV) | Egcal (eV) | ΔEgel (eV) |
---|---|---|---|---|---|---|---|---|---|---|
2a | 0.50 | −1.51 | 5.60 | 6.21 | 6.07 | 3.59 | −5.12 | −2.84 | 2.27 | 2.01 |
2b | 0.66 | −1.62 | 5.76 | 6.37 | 6.25 | 3.48 | −5.24 | −2.78 | 2.46 | 2.28 |
2c | 0.14 | −1.61 | 5.24 | 5.84 | 5.69 | 3.49 | −4.78 | −2.59 | 2.19 | 1.75 |
2d | 0.76 | −1.62 | 5.86 | 6.22 | 6.08 | 3.48 | −5.12 | −2.83 | 2.29 | 2.38 |
Compound | λmax ex (nm) | λmax cal (nm) | λemmax (nm) | f |
---|---|---|---|---|
2a | 355 | 413 (H-L+1) | 609 | 0.88 |
483 | 623 (H-L) | 0.73 | ||
2b | 332 | 393 (H-L+1) | 592 | 0.86 |
468 | 578 (H-L) | 0.69 | ||
2c | 370 | 418 (H-L+1) | 667 | 0.91 |
526 | 652 (H-L) | 0.68 | ||
2d | 311 | 406 (H-L+1) | 563 | 0.9 |
452 | 619 (H-L) | 0.69 |
Compound | Eoxonset (V) | Eredonset (V) | IP (eV) | EA (eV) | ΔEgel (eV) |
---|---|---|---|---|---|
p2a | 0.17 | −1.47 | 5.27 | 3.63 | 1.64 |
p2b | 0.01 | −1.63 | 5.11 | 3.47 | 1.64 |
p2c | −0.69 | −1.41 | 4.41 | 3.69 | 0.72 |
p2d | 0.09 | −1.28 | 5.19 | 3.82 | 1.37 |
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Zając, D.; Honisz, D.; Łapkowski, M.; Sołoducho, J. 2,1,3-Benzothiadiazole Small Donor Molecules: A DFT Study, Synthesis, and Optoelectronic Properties. Molecules 2021, 26, 1216. https://doi.org/10.3390/molecules26051216
Zając D, Honisz D, Łapkowski M, Sołoducho J. 2,1,3-Benzothiadiazole Small Donor Molecules: A DFT Study, Synthesis, and Optoelectronic Properties. Molecules. 2021; 26(5):1216. https://doi.org/10.3390/molecules26051216
Chicago/Turabian StyleZając, Dorota, Damian Honisz, Mieczysław Łapkowski, and Jadwiga Sołoducho. 2021. "2,1,3-Benzothiadiazole Small Donor Molecules: A DFT Study, Synthesis, and Optoelectronic Properties" Molecules 26, no. 5: 1216. https://doi.org/10.3390/molecules26051216