Effect of Structure Modification of Benzothiadiazole Acceptor Unit on the D-A-D-A-D Typed Oligothiophene Based Donor Materials for Organic Small Molecules Solar Cells: A Theoretical Study

doi:10.6023/cjoc201907032

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (3): 748-755.DOI: 10.6023/cjoc201907032 Previous Articles Next Articles

基于不同功能的苯并噻二唑为受体单元和低聚噻吩为给体单元的D-A-D-A-D型有机小分子光伏材料的理论计算研究

王丽辉, 白锁柱, 李东勇, 周宏

内蒙古民族大学化学化工学院内蒙古通辽 028000

收稿日期:2019-07-23 修回日期:2019-10-01 发布日期:2020-04-02
通讯作者: 王丽辉 E-mail:wanglihuihui@sina.com
基金资助:
内蒙古自然科学基金（No.2017MS0208）和内蒙古民族大学博士科研启动基金（No.BS450）资助项目.

Effect of Structure Modification of Benzothiadiazole Acceptor Unit on the D-A-D-A-D Typed Oligothiophene Based Donor Materials for Organic Small Molecules Solar Cells: A Theoretical Study

Wang Lihui, Bai Suozhu, Li Dongyong, Zhou Hong

College of Chemistry and Chemical Engineering, Inner Mongolia University for Nationalities, Tongliao, Neimenggu 028023

Received:2019-07-23 Revised:2019-10-01 Published:2020-04-02
Supported by:
Project supported by the Natural Science Foundation of Inner Mongolia Autonomous Region of China (No. 2017MS0208) and the Inner Mongolia University for Nationalities (IMUN) Doctoral Research Start-up Foundation (No. BS450).

1. 200748S.pdf.pdf(387KB)

Abstract

Four D-A-D-A-D structured organic small molecules (OSMs) DOBT-8T, BT-8T, FBT-8T and FFBT-8T have been designed for organic solar cells, which contain tetrathiophene as the core donor unit, bithiophene as the termial donor unit, combining different electron-withdrawing fragments DOBT, BT, FBT and FFBT as acceptor unit, respectively. The designed four OSMs were analyzed using density functional theory (DFT) and time dependent-DFT (TDDFT) calculations at B3LYP/6-31G(d) level. The effects of structure modification of benzothiadiazole acceptor unit on modulating the electron-donating ability of OSMs were fully investigated. Results showed that the geometrical structure, the band-gap, HOMO/LUMO energy levels, orbital spatial distribution, energetic driving force, open-circuit voltage and NPA atomic charge of these OSMs can be systematically altered by varying the electron-withdrawing properties with different benzothiadiazole acceptor units. Compared to other OSMs, FBT-8T displayed the more narrowed E_g and relatively deeper HOMO level with FBT as acceptor. FFBT-8T exhibited the most deep-lying HOMO level of the four designed OSMs and suitable E_g value by using FFBT as acceptor. The power conversion efficiencies (PCEs) of ca. 4.7% and ca. 5.2% were achieved by the photovoltaic devices based on FBT-8T:PC₆₁BM and FFBT-8T:PC₆₁BM systems, respectively, predicting with Scharber models. On the basis of these results, FBT-8T and FFBT-8T as potential OSMs donor materials for high-efficiency organic bulk hetero-junction solar cell were proposed.

Key words: B3LYP/6-31G (d), donor, OSMs, organic solar cell, benzothiadiazole, oligothiophenes

Cite this article

Wang Lihui, Bai Suozhu, Li Dongyong, Zhou Hong. Effect of Structure Modification of Benzothiadiazole Acceptor Unit on the D-A-D-A-D Typed Oligothiophene Based Donor Materials for Organic Small Molecules Solar Cells: A Theoretical Study[J]. Chinese Journal of Organic Chemistry, 2020, 40(3): 748-755.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Cui, C.; Guo, X.; Min, J.; Guo, B.; Cheng, X.; Zhang, M.; Brabec, C. J.; Li, Y. Adv. Mater. 2015, 27, 7469.
[2] Zhao, J.; Li, Y.; Yang, G.; Jiang, K.; Lin, H.; Ade, H.; Ma, W.; Yan, H. Nat. Energy 2016, 1, 1.
[3] Wan, J.; Xu, X.; Zhang, G.; Li, Y.; Peng, Q. Energy Environ. Sci. 2017, 10, 1739.
[4] Geng, Y.; Tang, A.; Tajima, K.; Zeng, Q.; Zhou, E. J. Mater. Chem. A 2019, 7, 64.
[5] Zhou, Z.; Xu, S.; Liu, W.; Zhang, C.; Hu, Q.; Liu, F. J. Mater. Chem. A 2017, 5, 3425.
[6] Du, J.; Biewer, M. C.; Stefan, M. C. J. Mater. Chem. A 2016, 4, 15771.
[7] Cheng, M.; Chen, C.; Yang, X.; Huang, J.; Zhang, F.; Xu, B.; Sun, L.-C. Chem. Mater. 2015, 27, 1808.
[8] (a) Wang, L.-H.; Wang, L.-J.; Xie, B.; Ji, C.-Y.; Li, Y.-Q. Dye Pigm. 2017, 140, 203.
(b) Wang, L.; Yin, L.; Ji, C.; Zhang, Y.; Gao, H.; Li, Y. Org. Electron. 2014, 15, 1138.
[9] Wang, J.-L.; Zhang, H.-J.; Liu, S.; Liu, K.-K.; Liu, F.; Wu, H.-B.; Cao, Y. Sol. RRL 2018, 2, 1800.
[10] Ni, W.; Wan, X.; Li, M.; Wang, Y.; Chen, Y. Chem. Commun. 2015, 51, 4936.
[11] Cho, A.; Song, C. E.; Lee, S. K.; Shin, W. S.; Lim, E. J. Mater. Sci. 2016, 51, 6770.
[12] (a) Chen, R.; Wang, Y.; Chen, T.; Li, H.; Zheng, C.; Yuan, K.; Wang, Z.; Tao, Y.; Zheng, C.; Huang, W. J. Phys. Chem. B 2015, 119, 583.
(b) Franco, F. C.; Padama, A. A. B. Polymer 2016, 97, 55.
(c) McCormick, T. M.; Bridges, C. R.; Carrera, E. I.; DiCarmine, P. M.; Gibson, G.-L.; Hollinger, J.; Kozycz, L. M.; Seferos, D. S. Macromolecules 2013, 46, 3879.
[13] (a) Becke, A. D. J. Chem. Phys. 1993, 98, 1372.
(b) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
(c) Becke, A. D. Phys. Rev. A 1988, 38, 3098.
[14] Lin, L.-Y.; Lu, C.-W.; Huang, W.-C.; Chen, Y.-H.; Lin, H.-W.; Wong, K.-T. Org. Lett. 2011, 13, 4962.
[15] Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B., G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A. Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Kobayashi, V. N. R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E; Cross, J. B.; Bakken, V.; Jaramillo, C. J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R.L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J., Dapprich, S.; Daniels, A. D.; Farkas, O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, Evision A.01, Gaussian, Inc., Wallingford CT, 2009.
[16] (a) Rutledge, L. R.; McAfee, S. M.; Welch, G. C. J. Phys. Chem. A 2014, 118, 7939.
(b) Sahu, H.; Panda, A. N. J. Phys. Chem. C 2015, 119, 22855.
[17] Wang, Z.; Song, C.; Li, J.; Li, P.; Zhang, H. J. Phys. Chem. C 2018, 123, 1069.
[18] (a) Frost, J. M.; Faist, M. A.; Nelson, J. Adv. Mater. 2010, 22, 4881.
(b) Zhang, G.; Musgrave, C. B. J. Phys. Chem. A 2007, 111, 1554.
[19] Wang, L.; Yin, L.; Ji, C.; Li, Y. Dye Pigm. 2015, 118, 37.
[20] Foster, J. P.; Weinhold, F. J. Am. Chem. Soc. 1980, 102, 7211.
[21] Irfan, M.; Iqbal, J.; Sadaf, S.; Eliasson, B.; Rana, U. A.; Ud-din Khan, S.; Ayub, K. Int. J. Quantum Chem. 2017, 117, 25363.
[22] Cui, Y.; Li, P.; Song, C.; Zhang, H. J. Phys. Chem. C 2016, 120, 28939.
[23] Zhang, L.; Shen, W.; He, R.; Tang, X.; Yang, Y.; Li, M. Mater. Chem. Phys. 2016, 175, 13.
[24] Sun, F.; Jin, R. Arab. J. Chem. 2017, 10, S2988.
[25] Liu, X.; He, R.; Shen, W.; Li, M. J. Power Sources 2014, 245, 217.
[26] Zhao, Z. W.; Pan, Q. Q.; Li, S. B.; Duan, Y. A.; Geng, Y.; Zhang, M.; Su, Z. M. J. Mol. Graphics Modell. 2017, 77, 9.
[27] Zhao, Z.-W.; Pan, Q.-Q.; Wu, S.-X.; Wu, Y.; Zhang, M.; Zhao, L.; Su, Z. M. Theor. Chem. Acc. 2018, 137, 1.
[28] Wang, J.-L.; Liu, K.-K.; Yan, J.; Wu, Z.; Liu, F.; Xiao, F.; Chang, Z.-F.; Wu, H.-B.; Cao, Y.; Russell, T. P. J. Am. Chem. Soc. 2016, 138, 7687.
[29] Pan, Q.-Q.; Li, S.-B.; Wu, Y.; Zhang, J.; Li, H.-B.; Geng, Y.; Su, Z.-M. New J. Chem. 2013, 1, 1.
[30] Bourass, M.; Touimi, B. A.; Hamidi, M.; Benzakour, M.; McHarfi, M.; Sfaira, M. J. Saudi Chem. Soc. 2016, 20, S415.
[31] Wan, J.; Xu, X.; Zhang, G.; Li, Y.; Feng, K.; Peng, Q. Energy Environ. Sci. 2017, 10, 1739.
[32] Taouali, W.; Casida, M. E.; Darghouth, A. A. M. H. M.; Alimi K. Comput. Mater. Sci. 2018, 150, 54.
[33] Bourass, M.; Touimi, B. A.; Benzakour, M.; McHarfi, M.; Jhilal, F.; Serein-Spirau, F.; Lère-Porte, J.-P.; Sotiropoulos, J.-M.; Bouzzine, S. M.; Bouachrine, M. J. Saudi Chem. Soc. 2017, 21, 563.
[34] Zhang, L.; Shen, W.; He, R.; Liu, X.; Tang, X.; Yang, Y.; Li, M. Org. Electron. 2016, 32, 134.
[35] Tai, C.-K.; Hsieh, C.-A.; Chang, K.-H.; Wang, B.-C. Res. Chem. Intermed. 2016, 42, 6907.
[36] Dennler, G.; Scharber, M. C. Brabec, C. J. Adv. Mater. 2009, 21, 1323.

基于不同功能的苯并噻二唑为受体单元和低聚噻吩为给体单元的D-A-D-A-D型有机小分子光伏材料的理论计算研究

Effect of Structure Modification of Benzothiadiazole Acceptor Unit on the D-A-D-A-D Typed Oligothiophene Based Donor Materials for Organic Small Molecules Solar Cells: A Theoretical Study

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Changjun Liu, Huiling Hu, Chenghong Liu, Chaojie Zhu, Tiandi Tang. Pd Supported on Mesoporous ETS-10 Zeolite Catalyst with Superior Catalytic Performances in Synthesizing 1,2-Diones from the Oxidation of Internal Alkynes [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2953-2960.
[2]	Min Wu, Bo Liu, Jialong Yuan, Qiang Fu, Rui Wang, Dawei Lou, Fushun Liang. Recent Progress in the C—S Bond Formation Reactions Mediated by Visible Light [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2269-2292.
[3]	Junping Du, Shanshan Feng, Jie Zhang, Yonghui Zhang, Shiwen Wang, Lifeng Han, Junli Chen. Tris(4-ethynylphenyl)amine-Based Conjugated Microporous Polymers and Its Photocatalytic Water Splitting Hydrogen Evolution [J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2967-2974.
[4]	Weikang Xia, Chuang Liu, Sheng Ye, Lei Wang, Ruiyuan Liu. Synthesis of A Sulfonamide-Substituted Benzothiadiazole-Based Fluorescent Dye and Study of Its Application for Long-Term Cancer Cell Tracking [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2535-2541.
[5]	Liqin Cao, Xiaoqin Yang, Maoqiu Li, Lin Liu, Junting Yu, Hua Tan. Synthesis and Electroluminescence Properties of Donor-Acceptor (D-A) Type Near-Infrared Iridium(III) Complex Luminescent Materials with Bipolar Transmission Features [J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1831-1838.
[6]	Yawen Xu, Jiankun Wang, Le Zhen, Guangji Wang. Research Progress of Small-Molecular Hydropersulfide Donors [J]. Chinese Journal of Organic Chemistry, 2021, 41(7): 2601-2609.
[7]	Ziyan Shao, Qingli Zhou, Jiancheng Wang, Rui Tang, Yuehai Shen. Sodium Iodide-Triphenylphosphine-Mediated Photoredox Alkylation of Aldimines [J]. Chinese Journal of Organic Chemistry, 2021, 41(7): 2676-2683.
[8]	Wang Wenyuan, Chen Hongjin, Zhang Gang, Zhang Rui, Liu Jian. Synthesis and Properties of Donor-Acceptor Type Electrochromic Materials Based on Triphenylamine and Quinoxaline [J]. Chinese Journal of Organic Chemistry, 2020, 40(8): 2513-2519.
[9]	Liu Hui, Zhang Xiaofeng, Cheng Jingzhao, Ye Dongnai, Chen Long, Wen Herui, Liu Shiyong. Direct C—H Arylation-Derived π-Conjugated Functional Materials for Device Applications [J]. Chinese Journal of Organic Chemistry, 2020, 40(4): 831-855.
[10]	Huang Guobao, Chen Zhilin, Wei Xiansheng, Chen Yu, Li Xiuying, Zhong Hui, Tan Mingxiong. Recent Progress on the Construction and Function of Macrocyclic Compounds Containing Hydrogen Bond Donors [J]. Chinese Journal of Organic Chemistry, 2020, 40(3): 614-624.
[11]	Zhou Xinyun, Xie Lingchao, Wu Kaile, Tan Songting. Synthesis and Photovoltaic Properties of Organic Dyes Containing Dendritic and 3D Triphenylamine Derivatives [J]. Chin. J. Org. Chem., 2019, 39(9): 2589-2598.
[12]	Hu Yuefu, Cui Guiling, Huang Wencai, Yang Li, Qi Qingrong. Synthesis, Structural Characterization and Stability Evaluation of Metformin Hydrosulfide [J]. Chin. J. Org. Chem., 2019, 39(5): 1503-1508.
[13]	Liang Long, Liu Li-Na, Chen Xue-Qiang, Xiang Xuan, Ling Jun, Lu Zheng-Quan, Li Jing-Jing, Li Wei-Shi. Benzodithiophene/Benzothiadiazole-Based ADA-Type Optoelectronic Molecules: Influence of Fluorine Substitution [J]. Chin. J. Org. Chem., 2019, 39(1): 157-169.
[14]	Sun Yanna, Gao Huanhuan, Zhang Yamin, Wang Yunchuang, Kan Bin, Wan Xiangjian, Zhang Hongtao, Chen Yongsheng. An Efficient Ternary Organic Solar Cell with a Porphyrin Based Small Molecule Donor and Two Fullerene Acceptors [J]. Chin. J. Org. Chem., 2018, 38(1): 228-236.
[15]	Xu Dingjian, Meng Lichen, Xu Hang, Yao Xiaoquan. Ligand-Triggered, Copper Catalyzed Synthesis of Peresters and Allylic Ester from Aldehydes [J]. Chin. J. Org. Chem., 2017, 37(5): 1205-1212.