Citation: Shao Rong, Yang Xinbo, Yin Shiwei, Wang Wenliang. Molecular Design of Benzothiadiazole Derivatives Electron Acceptors and Matching of Donor-Acceptor Materials[J]. Acta Chimica Sinica, ;2016, 74(8): 676-682. doi: 10.6023/A16050268 shu

Molecular Design of Benzothiadiazole Derivatives Electron Acceptors and Matching of Donor-Acceptor Materials

1.
Key Laboratory for Macromolecular Science of Shaanxi Province, School of Chemistry & Chemical Engineering, Shaanxi Normal University, Xi'an 710119, China

Corresponding author: Wang Wenliang, wlwang@snnu.edu.cn
Received Date: 30 May 2016

Fund Project: the National Natural Science Foundation of China 21473108the National Natural Science Foundation of China 21173139Shaanxi Innovative Team of Key Science and Technology 2013KCT-17

Figures(7)

To better understand the relationships between the microstructure and the optoelectronic characteristics of the electron acceptor and to meet the needs of donor-acceptor materials with excellent optical properties for solar cell, a series of acceptor molecules with A'-π-A-π-A' type are designed. In these molecules, the core framework of benzothiadiazole is used as an acceptor (A), three kinds of conjugated heterocyclics (A') with different abilities of electron-withdrawing and steric effects are applied as the terminals, and various conjugated structures, such as the double bond, thiophene, benzothiophene and vinyl thiophene, are utilized as π-bridge, respectively. Their geometric configurations, the characteristics of frontier molecular orbital, optical properties, as well as the electronic reorganization energy are predicted by DFT-B3LYP and TD-DFT-CAM-B3LYP. Solvent effects from acetone and chlorobenzene on molecular properties are studied. Furthermore, the Donor-Acceptor (D-A) interfaces are respectively constructed by combining the excellent acceptors with the selected two donors. The DFT-D3 method is used to scan the binding energy of D-A complex, in order to determine the stacked displacement of the interface. The degree of interface recombination is evaluated by calculating electronic coupling (V_if) between HOMO of donors and LUMO of acceptors. The results show that modifying benzothiadiazole with a reasonable substituent is an effective way to adjust LUMO energy levels and lead to the noticeable variation of the energy gap. Combining planar electron acceptor materials (A'-π-A-π-A' type) with non-planar electron donor materials (D), to form the optical active layer is a practical approach for preventing interface recombination and achieving high open-circuit voltage (V_oc). Considering ΔE_L, V_if, light absorption efficiency, and solvation effect, D1-1aγ and D1-2aγ combinations are the most promising candidates of optical active layer materials in organic solar cell.
- benzothiadiazole derivatives,
- electronic acceptors,
- Donor-Acceptor interface,
- electronic coupling,
- the power conversion efficiency
1. [1]
  Sariciftci, N. S.; Smilowitz, L.; Heeger, A. J.; Wudl, F. Science 1992, 258, 1474. doi: 10.1126/science.258.5087.1474
2. [2]
  Anthony, J. E.; Facchetti, A.; Heeney, M.; Marder, S. R.; Zhan, X. Adv. Mater. 2010, 22, 3876. doi: 10.1002/adma.200903628
3. [3]
  Meng, Q. B. Acta Chim. Sinica 2015, 73, 161. doi: 10.6023/A1503E001
4. [4]
  Carlotto, S. J. Phys. Chem. A 2014, 118, 4808. doi: 10.1021/jp503040n
5. [5]
  Armin, A.; Kassal, I.; Shaw, P. E.; Hambsch, M.; Stolterfoht, M.; Lyons, D. M.; Li, J.; Shi, Z.; Burn, P. L.; Meredith, P. J. Am. Chem. Soc. 2014, 136, 11465. doi: 10.1021/ja505330x
6. [6]
  Mishra, A.; Bäuerle, P. Angew. Chem. Int. Ed. 2012, 51, 2020. doi: 10.1002/anie.201102326
7. [7]
  Walker, B.; Liu, J.; Kim, C.; Welch, G. C.; Park, J. K.; Lin, J.; Zalar, P.; Proctor, C. M.; Seo, J. H.; Bazan, G. C.; Nguyen, T.-Q. Energy Environ. Sci. 2013, 6, 952. doi: 10.1039/c3ee24351f
8. [8]
  Wang, Z.; Uemura, Y.; Zhou, Y.; Miyadera, T.; Azumi, R.; Yoshida, Y.; Chikamatsu, M. ACS Appl. Mater. Interfaces 2015, 7, 10814. doi: 10.1021/acsami.5b01723
9. [9]
  Heremans, P.; Cheyns, D.; Rand, B. P. Acc. Chem. Res. 2009, 42, 1740. doi: 10.1021/ar9000923
10. [10]
  Reese, M. O.; Nardes, A. M.; Rupert, B. L.; Larsen, R. E.; Olson, D. C.; Lloyd, M. T.; Shaheen, S. E.; Ginley, D. S.; Rumbles, G.; Kopidakis, N. Adv. Funct. Mater. 2010, 20, 3476. doi: 10.1002/adfm.v20:20
11. [11]
  Fu, Y.; Wang, F.; Zhang, Y.; Fang, X.; Lai, W.; Huang, W. Acta Chim. Sinica 2014, 72, 158. doi: 10.6023/A13111142
12. [12]
  Dou, C.; Chen, D.; Iqbal, J.; Yuan, Y.; Zhang, H.; Wang, Y. Langmuir 2011, 27, 6323. doi: 10.1021/la200382b
13. [13]
  Woo, C. H.; Holcombe, T. W.; Unruh, D. A.; Sellinger, A. Chem. Mater. 2010, 22, 1673. doi: 10.1021/cm903067a
14. [14]
  Wolfer, P.; Schwenn, P. E.; Pandey, A. K.; Fang, Y.; Stingelin, N.; Burn, P. L.; Meredith, P. J. Mater. Chem. A. 2013, 1, 5989. doi: 10.1039/c3ta10554g
15. [15]
  Bloking, J. T.; Han, X.; Higgs, A. T.; Kastrop, J. P.; Pandey, L.; Norton, J. E.; Risko, C.; Chen, C. E.; Bredas, J.-E.; McGehee, M. D.; Sellinger, A. Chem. Mater. 2011, 23, 5484. doi: 10.1021/cm203111k
16. [16]
  Barone, V.; Cossi, M. J. Phys. Chem. A 1998, 102, 1995. doi: 10.1021/jp9716997
17. [17]
  Schlenker, C. W.; Thompson, M. E. Chem. Commun. 2011, 47, 3702. doi: 10.1039/c0cc04020g
18. [18]
  Newton, M. D.; Sutin, N. Ann. Rev. Phys. Chem. 1984, 35, 437. doi: 10.1146/annurev.pc.35.100184.002253
19. [19]
  Barbara, P. F.; Meyer, T. J.; Ratner, M. A. J. Phys. Chem. 1996, 100, 13148. doi: 10.1021/jp9605663
20. [20]
  Lemaur, V.; Steel, M.; Beljonne, D.; Brédas, J.-L.; Cornil, J. J. Am. Chem. Soc. 2005, 127, 6077. doi: 10.1021/ja042390l
21. [21]
  Hsu, C. P. Acc. Chem. Res. 2009, 42, 509. doi: 10.1021/ar800153f
22. [22]
  Yang, Y. M.; Yin, S. W.; Li, L. L.; Yang, J. Y. Acta Chim. Sinica 2011, 69, 1991.
23. [23]
  Grimme, S. WIREs Comput. Mol. Sci. 2011, 1, 211. doi: 10.1002/wcms.30
24. [24]
  Liu, H.; Brémond, É.; Prlj, A.; Gonthier, J. F.; Corminboeuf, C. J. Phys. Chem. Lett. 2014, 5, 2320. doi: 10.1021/jz501078s
25. [25]
  Guan, L.; Wang, W. L.; Shao, R.; Liu, F. Y.; Yin, S. W. J. Mol. Model. 2015, 21, 126-1. doi: 10.1007/s00894-015-2677-2
26. [26]
  Zhan, X.; Facchetti, A.; Barlow, S.; Marks, T. J.; Ratner, M. A.; Wasielewski, M. R.; Marder, S. R. Adv. Mater. 2011, 23, 268. doi: 10.1002/adma.v23.2
27. [27]
  Shao, R.; Wang, W. L.; Yang, X. B.; Yin, X. W. Sci. China-Chem. 2016, 46, 699.
28. [28]
  Liu, X.; Su, S. J.; Cao, Y. Polymer Bulletin 2014, 12, 68.
29. [29]
  Nalwa, H. S. Handbook of Advanced Electronic and Photonic Materials and Device, Academic San Diego, CA, 2001.
30. [30]
  Fitzner, R.; Reinold, E.; Mishra, A. Adv. Funct. Mater. 2011, 21, 897. doi: 10.1002/adfm.201001639
31. [31]
  Lin, L. Y.; Chen, Y. H.; Huang, Z. Y.; Lin, H. W.; Chou, S. H.; Lin, F.; Chen, C. W.; Liu, Y. H.; Wong, K. T. J. Am. Chem. Soc. 2011, 133, 15822. doi: 10.1021/ja205126t
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