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

doi:10.6023/A16050268

Acta Chim. Sinica ›› 2016, Vol. 74 ›› Issue (8): 676-682.DOI: 10.6023/A16050268 Previous Articles Next Articles

Article

苯并噻二唑类电子受体材料分子设计与给-受体的理论匹配

邵绒, 杨鑫博, 尹世伟, 王文亮

陕西省大分子科学重点实验室陕西师范大学化学化工学院西安 710119

投稿日期:2016-05-30 发布日期:2016-08-10
通讯作者: 王文亮 E-mail:wlwang@snnu.edu.cn
基金资助:
项目受国家自然科学基金（Nos. 21173139，21473108）和陕西省重点科技创新团队基金（No. 2013KCT-17）资助.

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

Shao Rong, Yang Xinbo, Yin Shiwei, Wang Wenliang

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

Received:2016-05-30 Published:2016-08-10
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21173139, 21473108) and Shaanxi Innovative Team of Key Science and Technology (No. 2013KCT-17).

1. Molecular Design of Benzothiadiazole Derivatives Electron Acceptors and Matching of Donor-Acceptor Materials.PDF(400KB)

Abstract

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.

Key words: benzothiadiazole derivatives, electronic acceptors, Donor-Acceptor interface, electronic coupling, the power conversion efficiency

Cite this article

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

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苯并噻二唑类电子受体材料分子设计与给-受体的理论匹配

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

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