Citation: 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]. Chinese Journal of Organic Chemistry, ;2019, 39(1): 157-169. doi: 10.6023/cjoc201808034 shu

Benzodithiophene/Benzothiadiazole-Based ADA-Type Optoelectronic Molecules: Influence of Fluorine Substitution

Liang Long ^a,b,† ,
Liu Li-Na ^b,† ,
Chen Xue-Qiang ^b ,
Xiang Xuan ^b ,
Ling Jun ^c ,
Lu Zheng-Quan ^a ,
Li Jing-Jing ^a ,
Li Wei-Shi ^a,b,,

a.
Zhengzhou Engineering Research Center for High Performance Organic Functional Materials, Zhengzhou Institute of Technology, Zhengzhou 450044
b.
Key Laboratory of Synthetic and Self-assembly Chemistry for Organic Functional Molecules, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
c.
Department of Polymer Science and Engineering, Zhejiang University, Hangzhou 320027

Corresponding author: Li Wei-Shi, liws@mail.sioc.ac.cn

^†

Received Date: 28 August 2018
Revised Date: 25 October 2018
Available Online: 11 January 2018
Fund Project: the Strategic Priority Research Program of Chinese Academy of Sciences XDB20020000the Science and Technology Open Cooperation Projects of Henan Province 162106000018Project supported by the National Natural Science Foundation of China (Nos. 21474129, 21674125, 51761145043), the Strategic Priority Research Program of Chinese Academy of Sciences (No. XDB20020000), the Science and Technology Open Cooperation Projects of Henan Province (Nos. 162106000018, 172106000067) and the Zhengzhou Institute of Technologythe National Natural Science Foundation of China 21674125the Science and Technology Open Cooperation Projects of Henan Province 172106000067the National Natural Science Foundation of China 21474129the National Natural Science Foundation of China 51761145043

Figures(11)

Fluorination on conjugated components is one of popular strategies to modify organic optoelectronic materials. Following the research of a benzodithiophene/benzothiadiazole ADA-type optoelectronic molecule, two benzothiadiazole (BT) units were fluorinated with different numbers and positions, and the change in basic properties and performances for field-effect transistors and organic solar cells was investigated. It was found that when the F-substitution number increases, the molecule enhances thermal stability, decreases solubility, lowers HOMO and LUMO energy levels, but almost does not alter light absorption range. Furthermore, investigations on organic field-effect transistors found the molecular hole mobility reduces with only one F-substituent at outer position of BT units, while increases up to 0.27 cm²·V^-1·s^-1 with two F substituents on BT units. However, when these materials are applied in organic solar cells, the fluorinated ones enhance open-circuit voltage, but deteriorate active layer morphology, finally leading to decrease in short-circuit current and device efficiency.
- organic optoelectronic materials,
- fluorination effect,
- organic field-effect transistors,
- organic solar cells
1. [1]
  (a) Brabec, C. J.; Gowrisanker, S.; Halls, J. J. M.; Laird, D.; Jia, S.; Williams, S. P. Adv. Mater. 2010, 22, 3839.
  (b) Facchetti, A. Chem. Mater. 2011, 23, 733.
  (c) Ilmi, R.; Haque, A.; Khan, M. S. Org. Electr. 2018, 58, 53.
  (d) Guo, H.; Li, W.; Chang, C.; Guo, X.; Zhang, M. Chin. J. Chem. 2018, 36, 502.
  (e) Liang, X.; Wang, Z.; Wang, L.; Hanif, M.; Hu, D.; Su, S.; Xie, Z.; Gao, Y.; Yang, B.; Ma, Y. Chin. J. Chem. 2017, 35, 1559.
2. [2]
  (a) Zhao, X.; Zhan, X. Chem. Soc. Rev. 2011, 40, 3728.
  (b) Di, C.; Yu, G.; Liu, Y.; Zhu, D. J. Phys. Chem. B 2007, 111, 14083.
  (c) Zaumseil, J.; Sirringhaus, H. Chem. Rev. 2007, 107, 1296.
3. [3]
  (a) Reineke, S.; Lindner, F.; Schwartz, G.; Seidler, N.; Walzer, K.; Lüssem, B.; Leo, K. Nature 2009, 459, 234.
  (b) Yang, X.; Zhou, G.; Wong, W. Y. Chem. Soc. Rev. 2015, 44, 8484.
  (c) Jou, J. H.; Kumar, S.; Agrawal, A.; Li, T. H.; Sahoo, S. J. Mater. Chem. C 2015, 3, 2974.
4. [4]
  Chem, H.; Chen, Y.; Li, Z.; Yang, Q.; Xin, L. Chin. J. Org. Chem. 2012, 32, 46(in Chinese).
5. [5]
  (a) Zhang, G.; Zhang, K.; Yin, Q.; Jiang, X. F.; Wang, Z.; Xin, J.; Ma, W.; Yan, H.; Huang, F.; Cao, Y. J. Am. Chem. Soc. 2017, 139, 2387.
  (b) Li, M.; Gao, K.; Wan, X.; Zhang, Q.; Kan, B.; Xia, R.; Liu, F.; Yang, X.; Feng, H.; Ni, W.; Wang, Y.; Peng, J.; Zhang, H.; Liang, Z.; Yip, H.-L.; Peng, X.; Cao, Y.; Chen, Y. Nat. Photonics 2017, 11, 85.
  (c) Zhao, J.; Li, Y.; Yang, G.; Jiang, K.; Lin, H.; Ade, H.; Ma, W.; Yan, H. Nat. Energy 2016, 1, 15027.
  (d) Deng, D.; Zhang, Y. J.; Zhang, J. Q.; Wang, Z. Y.; Zhu, L. Y.; Fang, J.; Xia, B. Z.; Wang, Z.; Lu, K.; Ma, W.; Wei, Z. X. Nat. Commun. 2016, 7, 13740.
  (e) Li, Y. F. Acc. Chem. Res. 2012, 45, 723.
  (f) Yang, F.; Li, C.; Lai, W.; Zhang, A.; Huang, H.; Li, W. Mater. Chem. Front. 2017, 1, 1389.
  (g) Liu, W.; Zhou, Z.; Vergote, T.; Xu, S.; Zhu, X. Mater. Chem. Front. 2017, 1, 2349.
6. [6]
  (a) Zhang, J.; Zhang, Y.; Fang, J.; Lu, K.; Wang, Z.; Ma, W.; Wei, Z. J. Am. Chem. Soc. 2015, 137, 8176.
  (b) Li, G.; Chu, C. W.; Shrotriya, V.; Huang, J.; Yang, Y. Appl. Phys. Lett. 2006, 88, 253503.
  (c) Kim, J. Y.; Lee, K.; Coates, N. E.; Moses, D.; Nguyen, T. Q.; Dante, M.; Heeger, A. J. Science 2007, 317, 222.
  (d) He, Z.; Zhong, C.; Huang, X.; Wong, W.-Y.; Wu, H.; Chen, L.; Su, S.; Cao, Y. Adv. Mater. 2011, 23, 4636.
7. [7]
  (a) Li, G.; Shrotriya, V.; Huang, J. S.; Yao, Y.; Moriarty, T.; Emery, K.; Yang, Y. Nat. Mater. 2005, 4, 864.
  (b) Peet, J.; Kim, J. Y.; Coates, N. E.; Ma, W. L.; Moses, D.; Heeger, A. J.; Bazan, G. C. Nat. Mater. 2007, 6, 497.
  (c) Zimmerman, J. D.; Xiao, X.; Renshaw, C. K.; Wang, S.; Diev, V. V.; Thompson, M. E.; Forrest, S. R. Nano Lett. 2012, 12, 4366.
  (d) Wang, J. L.; Xiao, F.; Yan, J.; Wu, Z.; Liu, K. K.; Chang, Z. F.; Zhang, R. B.; Chen, H.; Wu, H. B.; Cao, Y. Adv. Funct. Mater. 2016, 26, 1803.
  (e) Liu, X.; Ye, L.; Zhao, W.; Zhang, S.; Li, S.; Su, G. M.; Wang, C.; Ade, H.; Hou, J. Mater. Chem. Front. 2017, 1, 2057.
8. [8]
  (a) Neugebauer, H.; Brabec, C.; Hummelen, J. C.; Sariciftci, N. S. Sol. Energy Mater. Sol. Cells 2000, 61, 35.
  (b) Lu, L.; Kelly, M. A.; You, W.; Yu, L. Nat. Photonics 2015, 9, 491.
  (c) Min, J.; Luponosov, Y. N.; Gasparini, N.; Richter, M.; Bakirov, A. V.; Shcherbina, M. A.; Chvalun, S. N.; Grodd, L.; Grigorian, S.; Ameri, T.; Ponomarenko, S. A.; Brabec, C. J. Adv. Energy Mater. 2015, 5, 1500386.
9. [9]
  Meng, L.; Zhang, Y.; Wan, X.; Li, C.; Zhang, X.; Wang, Y.; Ke, X.; Xiao, Z.; Ding, L.; Xia, R.; Yip, H.-L.; Cao, Y.; Chen, Y. Science 2018, 361, 1094. doi: 10.1126/science.aat2612
10. [10]
  (a) Lei, Y.; Deng, P.; Zhang, Q.; Xiong, Z.; Li, Q.; Mai, J.; Lu, X.; Zhu, X.; Ong, B. S. Adv. Funct. Mater. 2018, 28, 1706372.
  (b) Kang, I.; Yun, H. J.; Chung, D. S.; Kwon, S. K.; Kim, Y. H. J. Am. Chem. Soc. 2013, 135, 14896.
11. [11]
  (a) Xiao, S.; Zhang, Q.; You, W. Adv. Mater. 2017, 29, 1601391.
  (b) Zhang, Z.; Li, Y. Sci. China: Chem. 2015, 58, 192.
  (c) Chen, H.; Hou, J.; Zhang, S.; Liang, Y.; Yang, G. W.; Yang, Y.; Yu, L.; Wu, Y.; Li, G. Nat. Photonics 2009, 3, 649.
12. [12]
  (a) Tang, M. L.; Bao, Z. A. Chem. Mater. 2011, 23, 446.
  (b) Oh, J.; Kranthiraja, K.; Lee, C.; Gunasekar, K.; Kim, S.; Ma, B.; Kim, B. J.; Jin, S.-H. Adv. Mater. 2016, 28, 10016.
  (c) Stuart, A. C.; Tumbleston, J. R.; Zhou, H.; Li, W.; Liu, S.; Ade, H.; You, W. J. Am. Chem. Soc. 2013, 135, 1806.
13. [13]
  (a) Zhang, M.; Guo, X.; Zhang, S.; Hou, J. Adv. Mater. 2014, 26, 1118.
  (b) Kawashima, K.; Fukuhara, T.; Suda, Y.; Suzuki, Y.; Koganezawa, T.; Yoshida, H.; Ohkita, H.; Osaka, I.; Takimiya, K. J. Am. Chem. Soc. 2016, 138, 10265.
14. [14]
  Reichenbacher, K.; Suss, H. I.; Hulliger, J. Chem. Soc. Rev. 2005, 34, 22. doi: 10.1039/B406892K
15. [15]
  Lu, L.; Yu, L. Adv. Mater. 2014, 26, 4413. doi: 10.1002/adma.v26.26
16. [16]
  (a) Yoon, M.-H.; DiBenedetto, S. A.; Facchetti, A.; Marks, T. J. J. Am. Chem. Soc. 2005, 127, 1348.
  (b) Heidenhain, S. B.; Sakamoto, Y.; Suzuki, T.; Miura, A.; Fujikawa, H.; Mori, T.; Tokito, S.; Taga, Y. J. Am. Chem. Soc. 2000, 122, 10240.
17. [17]
  Liang, Y.; Feng, D.; Wu, Y.; Tsai, S.-T.; Li, G.; Ray, C.; Yu, L. J. Am. Chem. Soc. 2009, 131, 7792. doi: 10.1021/ja901545q
18. [18]
  Son, H. J.; Wang, W.; Xu, T.; Liang, Y.; Wu, Y.; Li, G.; Yu, L. J. Am. Chem. Soc. 2011, 133, 1885. doi: 10.1021/ja108601g
19. [19]
  (a) Zhang, Y.; Chien, S.-C.; Chen, K.-S.; Yip, H.-L.; Sun, Y.; Davies, J. A.; Chen, F.-C.; Jen, A. K.-Y. Chem. Commun. 2011, 47, 11026.
  (b) Schroeder, B. C.; Huang, Z.; Ashraf, R. S.; Smith, J.; D¢ Angelo, P.; Watkins, S. E.; Anthopoulos, T. D.; Durrant, J. R.; McCulloch, I. Adv. Funct. Mater. 2012, 22, 1663.
20. [20]
  (a) Zhou, H.; Yang, L.; Stuart, A. C.; Price, S. C.; Liu, S.; You, W. Angew. Chem., Int. Ed. 2011, 50, 2995.
  (b) Peng, Q.; Liu, X.; Su, D.; Fu, G.; Xu, J.; Dai, L. Adv. Mater. 2011, 23, 4554.
21. [21]
  Hu, J.; Wang, X.; Chen, F.; Xiao, B.; Tang, A.; Zhou, E. Polymers 2017, 9, 516. doi: 10.3390/polym9100516
22. [22]
  (a) Roncali, J. Acc. Chem. Res. 2009, 42, 1719.
  (b) Li, Y.; Guo, Q.; Li, Z.; Pei, J.; Tian, W. Energy Environ. Sci. 2010, 3, 1427.
  (c) Walker, B.; Kim, C.; Nguyen, T.-Q. Chem. Mater. 2011, 23, 470.
  (d) Mishra, A.; Bauerle, P. Angew. Chem., Int. Ed. 2012, 51, 2020.
23. [23]
  Liang, L.; Wang, J.-T.; Xiang, X.; Ling, J.; Zhao, F.-G.; Li, W.-S. J. Mater. Chem. A 2014, 2, 15396. doi: 10.1039/C4TA03125C
24. [24]
  van der Poll, T. S.; Love, J. A.; Nguyen, T.-Q.; Bazan, G. C. Adv. Mater. 2012, 24, 3646. doi: 10.1002/adma.v24.27
25. [25]
  He, C.-Y.; Wu, C.-Z.; Zhu, Y.-L.; Zhang, X. Chem. Sci. 2014, 5, 1317. doi: 10.1039/C3SC53119H
26. [26]
  Mei, C.-Y.; Liang, L.; Zhao, F.-G.; Wang, J.-T.; Yu, L.-F.; Li, Y.-X.; Li, W.-S. Macromolecules 2013, 46, 7920. doi: 10.1021/ma401298g
27. [27]
  (a) Hohenberg, P.; Kohn, W. Phys. Rev. 1964, 136, B864.
  (b) Kohn, W.; Sham, L. J. Phys. Rev. 1965, 140, A1133.
  (c) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. 1988, B37, 785.
  (d) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
28. [28]
  (a) Hohenberg. P.; Kohn, W.; Phys. Rev. 1964, 136, B864(b) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B: Condens. Matter Mater. Phys. 1988, 37, 785.
29. [29]
  Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A. J.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, Gaussian, Inc., Wallingford CT, 2004.
30. [30]
  Wang, J.-L.; Chang, Z.-F.; Song, X.-X.; Liu, K.-K.; Jing, L.-M. J. Mater. Chem. 2015, 3, 9849.
1. [1]
  Yikai Wang , Xiaolin Jiang , Haoming Song , Nan Wei , Yifan Wang , Xinjun Xu , Cuihong Li , Hao Lu , Yahui Liu , Zhishan Bo . 氰基修饰的苝二酰亚胺衍生物作为膜厚不敏感型阴极界面材料用于高效有机太阳能电池. Acta Physico-Chimica Sinica, 2025, 41(3): 2406007-. doi: 10.3866/PKU.WHXB202406007
2. [2]
  Shuixing Dai , Jilei Jiang , Yuxiao Wang , Jinqi Hu , Minghua Huang . Application of Knoevenagel Reaction in Organic Chemistry Teaching. University Chemistry, 2025, 40(5): 334-341. doi: 10.12461/PKU.DXHX202405208
3. [3]
  Mengfei He , Chao Chen , Yue Tang , Si Meng , Zunfa Wang , Liyu Wang , Jiabao Xing , Xinyu Zhang , Jiahui Huang , Jiangbo Lu , Hongmei Jing , Xiangyu Liu , Hua Xu . Epitaxial Growth of Nonlayered 2D MnTe Nanosheets with Thickness-Tunable Conduction for p-Type Field Effect Transistor and Superior Contact Electrode. Acta Physico-Chimica Sinica, 2025, 41(2): 100016-. doi: 10.3866/PKU.WHXB202310029
4. [4]
  Xiaofang DONG , Yue YANG , Shen WANG , Xiaofang HAO , Yuxia WANG , Peng CHENG . Research progress of conductive metal-organic frameworks. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 14-34. doi: 10.11862/CJIC.20240388
5. [5]
  Lina Feng , Guoyu Jiang , Xiaoxia Jian , Jianguo Wang . Application of Organic Radical Materials in Biomedicine. University Chemistry, 2025, 40(4): 253-260. doi: 10.12461/PKU.DXHX202405171
6. [6]
  Qianlang Wang , Jijun Sun , Qian Chen , Quanqin Zhao , Baojuan Xi . The Appeal of Organophosphorus Compounds: Clearing Their Name. University Chemistry, 2025, 40(4): 299-306. doi: 10.12461/PKU.DXHX202405205
7. [7]
  Wendian XIE , Yuehua LONG , Jianyang XIE , Liqun XING , Shixiong SHE , Yan YANG , Zhihao HUANG . Preparation and ion separation performance of oligoether chains enriched covalent organic framework membrane. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1528-1536. doi: 10.11862/CJIC.20240050
8. [8]
  Fugui XI , Du LI , Zhourui YAN , Hui WANG , Junyu XIANG , Zhiyun DONG . Functionalized zirconium metal-organic frameworks for the removal of tetracycline from water. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 683-694. doi: 10.11862/CJIC.20240291
9. [9]
  Chao Liu , Huan Yu , Jiaming Li , Xi Yu , Zhuangzhi Yu , Yuxi Song , Feng Zhang , Qinfang Zhang , Zhigang Zou . Facile synthesis of hierarchical Ti₃C₂/Bi₁₂O₁₇Br₂ Schottky heterojunction with photothermal effect for solar-driven antibiotics photodegradation. Acta Physico-Chimica Sinica, 2025, 41(7): 100075-. doi: 10.1016/j.actphy.2025.100075
10. [10]
  Yi DING , Peiyu LIAO , Jianhua JIA , Mingliang TONG . Structure and photoluminescence modulation of silver(Ⅰ)-tetra(pyridin-4-yl)ethene metal-organic frameworks by substituted benzoates. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 141-148. doi: 10.11862/CJIC.20240393
11. [11]
  Mengzhen JIANG , Qian WANG , Junfeng BAI . Research progress on low-cost ligand-based metal-organic frameworks for carbon dioxide capture from industrial flue gas. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 1-13. doi: 10.11862/CJIC.20240355
12. [12]
  Wei Li , Jinfan Xu , Yongjun Zhang , Ying Guan . 共价有机框架整体材料的制备及食品安全非靶向筛查应用——推荐一个仪器分析综合化学实验. University Chemistry, 2025, 40(6): 276-285. doi: 10.12461/PKU.DXHX202406013
13. [13]
  Lewang Yuan , Yaoyao Peng , Zong-Jie Guan , Yu Fang . 二维共价有机框架作为光催化剂在有机合成中的研究进展. Acta Physico-Chimica Sinica, 2025, 41(8): 100086-. doi: 10.1016/j.actphy.2025.100086
14. [14]
  Wenxiu Yang , Jinfeng Zhang , Quanlong Xu , Yun Yang , Lijie Zhang . Bimetallic AuCu Alloy Decorated Covalent Organic Frameworks for Efficient Photocatalytic Hydrogen Production. Acta Physico-Chimica Sinica, 2024, 40(10): 2312014-. doi: 10.3866/PKU.WHXB202312014
15. [15]
  Aiai WANG , Lu ZHAO , Yunfeng BAI , Feng FENG . Research progress of bimetallic organic framework in tumor diagnosis and treatment. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1825-1839. doi: 10.11862/CJIC.20240225
16. [16]
  Feng Sha , Xinyan Wu , Ping Hu , Wenqing Zhang , Xiaoyang Luan , Yunfei Ma . Design of Course Ideology and Politics for the Comprehensive Organic Synthesis Experiment of Benzocaine. University Chemistry, 2024, 39(2): 110-115. doi: 10.3866/PKU.DXHX202307082
17. [17]
  Xinyu Zhu , Meili Pang . Application of Functional Group Addition Strategy in Organic Synthesis. University Chemistry, 2024, 39(3): 218-230. doi: 10.3866/PKU.DXHX202308106
18. [18]
  Tianyun Chen , Ruilin Xiao , Xinsheng Gu , Yunyi Shao , Qiujun Lu . Synthesis, Crystal Structure, and Mechanoluminescence Properties of Lanthanide-Based Organometallic Complexes. University Chemistry, 2024, 39(5): 363-370. doi: 10.3866/PKU.DXHX202312017
19. [19]
  Shicheng Yan . Experimental Teaching Design for the Integration of Scientific Research and Teaching: A Case Study on Organic Electrooxidation. University Chemistry, 2024, 39(11): 350-358. doi: 10.12461/PKU.DXHX202408036
20. [20]
  Yong Wang , Yingying Zhao , Boshun Wan . Analysis of Organic Questions in the 37th Chinese Chemistry Olympiad (Preliminary). University Chemistry, 2024, 39(11): 406-416. doi: 10.12461/PKU.DXHX202403009

Get Citation

PDF

XML

Metrics

PDF Downloads(10)
Abstract views(1990)
HTML views(307)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142