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
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