Citation: Xia Debin, Zhang Fangyuan, Liu Zhigang, Meng Linghao, Fan Ruiqing, Yang Yulin. Tetra-phthalimide end-fused bifluorenylidene: Synthesis and characterization[J]. Chinese Chemical Letters, ;2019, 30(1): 259-262. doi: 10.1016/j.cclet.2018.01.033 shu

Tetra-phthalimide end-fused bifluorenylidene: Synthesis and characterization

MIIT Key Laboratory of Critical Materials Technology for New Energy Conversion and Storage, School of Chemistry and Chemical Engineering, Harbin Institute of Technology, Harbin 150001, China

Corresponding author: Xia Debin, xia@hit.edu.cn Fan Ruiqing, fanruiqing@hit.edu.cn Yang Yulin, ylyang@hit.edu.cn
Received Date: 20 December 2017
Revised Date: 8 January 2018
Accepted Date: 17 January 2018
Available Online: 31 January 2018

Figures(7)

A novel electron acceptor, namely, tetra-phthalimide end-fused bifluorenylidene (3D-imide) was designed and synthesized. In comparison to its framework analogue 12, 12'-bidibenzo[b, h]fluorenylidene (BF-3), the electron withdrawing capability and optical absorption were strengthened and enlarged, respectively. Moreover, photoluminescence quenching experiments were carried out, which confirmed 3D-imide could be a good candidate for nonfullene organic photovoltaics. Finally, we gained more insight into its electronic properties through density functional theory calculation.
- Bifluorenylidene,
- Polycycles,
- Electron acceptor,
- Twisting,
- Three dimensional
1. [1]
  N. Assadi, S. Pogodin, S. Cohen, I. Agranat, Struct. Chem. 25(2014) 1901-1902.
2. [2]
  C. Wentrup, M.J. Regimbald-Krnel, D. Müller, P. Comba, Angew. Chem. Int. Ed. 55(2016) 14600-14605. doi: 10.1002/anie.201607415
3. [3]
  F.G. Brunetti, X. Gong, M. Tong, A.J. Heeger, F. Wudl, Angew. Chem. Int. Ed. 49(2010) 532-536. doi: 10.1002/anie.200905117
4. [4]
  A. Mishra, P. Bäuerle, Angew. Chem. Int. Ed. 51(2012) 2020-2067. doi: 10.1002/anie.201102326
5. [5]
  Y. Lin, Y. Li, X. Zhan, Chem. Soc. Rev. 41(2012) 4245-4272. doi: 10.1039/c2cs15313k
6. [6]
  P.M. Beaujuge, J.M.J. Fréchet, J. Am. Chem. Soc. 133(2011) 20009-20029. doi: 10.1021/ja2073643
7. [7]
  S. Kawata, J. Furudate, T. Kimura, et al., J. Mater. Chem. C 5(2017) 4909-4914. doi: 10.1039/C7TC00315C
8. [8]
  H.U. Kim, J.H. Kim, H. Suh, et al., Chem. Commun. 49(2013) 10950-10952. doi: 10.1039/c3cc46557h
9. [9]
  Y. Lu, B. Wu, P. Deng, F. Zhu, B.S. Ong, New J. Chem. 41(2017) 6822-6827. doi: 10.1039/C7NJ00656J
10. [10]
  H. Minaki, S. Kawata, J. Furudate, et al., Chem. Lett 46(2017) 1126-1129. doi: 10.1246/cl.170437
11. [11]
  E. Molins, C. Miravitlles, E. Espinosa, M. Ballester, J. Org. Chem. 67(2002) 7175-7178. doi: 10.1021/jo010979m
12. [12]
  A. Takai, D.J. Freas, T. Suzuki, et al., Org. Chem. Front. 4(2017) 650-657. doi: 10.1039/C7QO00125H
13. [13]
  M. Wielopolski, M. Marszalek, F.G. Brunetti, et al., J. Mater. Chem. C 4(2016) 3798-3808.
14. [14]
  S. Carlotto, J. Phys. Chem. A 118(2014) 4808-4815. doi: 10.1021/jp503040n
15. [15]
  X. Gong, M. Tong, F.G. Brunetti, et al., Adv. Mater. 23(2011) 2272-2277. doi: 10.1002/adma.201003768
16. [16]
  L. Amalia, G. Michal, A. Israel, Lett. Org. Chem. 3(2006) 579-584. doi: 10.2174/157017806778559572
17. [17]
  D. Xia, T. Marszalek, M. Li, et al., Org. Lett. 17(2015) 3074-3077. doi: 10.1021/acs.orglett.5b01343
18. [18]
  X. Guo, H.N. Tsao, P. Gao, et al., RSC Adv. 54(2014) 54130-54133.
19. [19]
  F.G. Brunetti, A. Varotto, N.A. Batara, F. Wudl, Chem.-Eur. J. 17(2011) 8604-8608. doi: 10.1002/chem.201100442
20. [20]
  O.Y. Park, H.U. Kim, J.B. Park, D.H. Hwang, J. Nanosci. Nanotechnol. 14(2014) 8225-8230. doi: 10.1166/jnn.2014.9887
21. [21]
  D. Xia, X. Guo, M. Wagner, et al., Cryst. Growth Des. 17(2017) 2816-2821. doi: 10.1021/acs.cgd.7b00272
22. [22]
  Y. Ie, T. Sakurai, S. Jinnai, et al., Chem. Commun. 49(2013) 8386-8388. doi: 10.1039/c3cc43925a
23. [23]
  C. Dou, X. Long, Z. Ding, et al., Angew. Chem. Int. Ed. 55(2016) 1436-1440. doi: 10.1002/anie.201508482
24. [24]
  R. Zhao, C. Dou, Z. Xie, J. Liu, L. Wang, Angew. Chem. Int. Ed. 55(2016) 5313-5317. doi: 10.1002/anie.201601305
25. [25]
  Y. Min, C. Dou, H. Tian, et al., Angew. Chem. Int. Ed. 57(2018) 2000-2004. doi: 10.1002/anie.201712986
1. [1]
  Yuhang Li , Yang Ling , Yanhang Ma . Application of three-dimensional electron diffraction in structure determination of zeolites. Chinese Journal of Structural Chemistry, 2024, 43(4): 100237-100237. doi: 10.1016/j.cjsc.2024.100237
2. [2]
  Chao Ma , Peng Guo , Zhongmin Liu . DNL-16: A new zeolitic layered silicate unraveled by three-dimensional electron diffraction. Chinese Journal of Structural Chemistry, 2024, 43(4): 100235-100235. doi: 10.1016/j.cjsc.2024.100235
3. [3]
  Wenxu Liu , Feng Han , Boxuan Wang , Huayi Liu , Xiaobin Gu , Xin Zhang , Yao Liu . Comprehensive Chemical Experiment: Design, Synthesis, and Photoelectronic Properties Study of Fully Non-Fused Ring Electron Acceptors. University Chemistry, 2025, 40(10): 263-275. doi: 10.12461/PKU.DXHX202412021
4. [4]
  Rong-Nan Yi , Wei-Min He . Electron donor-acceptor complex enabled arylation of dithiocarbamate anions with thianthrenium salts under aqueous micellar conditions. Chinese Chemical Letters, 2024, 35(11): 110194-. doi: 10.1016/j.cclet.2024.110194
5. [5]
  Hongping Zhao , Weiming Yuan . Merging catalytic electron donor-acceptor complex and copper catalysis: Enantioselective radical carbocyanation of alkenes. Chinese Chemical Letters, 2025, 36(10): 110894-. doi: 10.1016/j.cclet.2025.110894
6. [6]
  Shiyu Hou , Maolin Sun , Liming Cao , Chaoming Liang , Jiaxin Yang , Xinggui Zhou , Jinxing Ye , Ruihua Cheng . Computational fluid dynamics simulation and experimental study on mixing performance of a three-dimensional circular cyclone-type microreactor. Chinese Chemical Letters, 2024, 35(4): 108761-. doi: 10.1016/j.cclet.2023.108761
7. [7]
  Yang LU , Liangliang HUANG , Wei ZHAO , Xin WANG , Yanfeng BI . Syntheses, proton conduction, and transport mechanism of two three-dimensional lanthanum phosphite-oxalates. Chinese Journal of Inorganic Chemistry, 2025, 41(10): 2127-2137. doi: 10.11862/CJIC.20250149
8. [8]
  Yifan LIU , Zhan ZHANG , Rongmei ZHU , Ziming QIU , Huan PANG . A three-dimensional flower-like Cu-based composite and its low-temperature calcination derivatives for efficient oxygen evolution reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 979-990. doi: 10.11862/CJIC.20240008
9. [9]
  Wenhao Chen , Muxuan Wu , Han Chen , Lue Mo , Yirong Zhu . Cu₂Se@C thin film with three-dimensional braided structure as a cathode material for enhanced Cu²⁺ storage. Chinese Chemical Letters, 2024, 35(5): 108698-. doi: 10.1016/j.cclet.2023.108698
10. [10]
  Hui Gu , Mingyue Gao , Kuan Shen , Tianli Zhang , Junhao Zhang , Xiangjun Zheng , Xingmei Guo , Yuanjun Liu , Fu Cao , Hongxing Gu , Qinghong Kong , Shenglin Xiong . F127 assisted fabrication of Ge/rGO/CNTs nanocomposites with three-dimensional network structure for efficient lithium storage. Chinese Chemical Letters, 2024, 35(9): 109273-. doi: 10.1016/j.cclet.2023.109273
11. [11]
  Bangdi GE , Xiaowei SONG , Zhiqiang LIANG . A bifunctional three-dimensional Eu-MOF fluorescent probe for highly sensitive detection of 2, 4, 6-trinitrophenol and tetracycline. Chinese Journal of Inorganic Chemistry, 2025, 41(10): 2165-2174. doi: 10.11862/CJIC.20250190
12. [12]
  Yubang Liu , Jiaxin Lin , Huayu Liang , Yinwu Li , Zhuofeng Ke . Computational insights into three-centre four-electron bridging hydride bond in boryl type PBP-M dihydride complexes^{✰ ✩}. Chinese Chemical Letters, 2025, 36(5): 110291-. doi: 10.1016/j.cclet.2024.110291
13. [13]
  Yan Fan , Jiao Tan , Cuijuan Zou , Xuliang Hu , Xing Feng , Xin-Long Ni . Unprecedented stepwise electron transfer and photocatalysis in supramolecular assembly derived hybrid single-layer two-dimensional nanosheets in water. Chinese Chemical Letters, 2025, 36(4): 110101-. doi: 10.1016/j.cclet.2024.110101
14. [14]
  Ning Liu , Man Tian , Ye Zhang , Jinming Yang , Zhihao Wang , Wangxi Dai , Guixiang Quan , Jianqiu Lei , Xiaodong Zhang , Liang Tang . Three-dimensional MIL-88A(Fe)-derived α-Fe₂O₃ and graphene composite for efficient photo-Fenton-like degradation of ciprofloxacin. Chinese Chemical Letters, 2025, 36(12): 111063-. doi: 10.1016/j.cclet.2025.111063
15. [15]
  Shuqi Chen , Cankun Zhang , Xiaonuo Dong , Hui-Jun Zhang , Jianbin Lin . Synthesis and photophysical properties of alternating donor-acceptor conjugated nanorings. Chinese Chemical Letters, 2025, 36(6): 110354-. doi: 10.1016/j.cclet.2024.110354
16. [16]
  Zhaoyue Lü , Tiantian Chai , Yichao Jin , Xiao Wang , Ye Zou , Lijiang Zhang , Jiankang Feng , Mengtong Zhang , Shuo Wang , Chichong Lu , Guofan Jin . Asymmetrical carbazole-benzonitrile-based TADF emitters designed by alternate donor-acceptor strategy. Chinese Chemical Letters, 2025, 36(6): 110817-. doi: 10.1016/j.cclet.2025.110817
17. [17]
  Xinyi Zhao , Yuai Duan , Zihan Liu , Hua Geng , Yaping Li , Zhongfeng Li , Tianyu Han . Mapping sweat pores for biometric identification based on a donor-acceptor hydrophilic fluorescent probe. Chinese Chemical Letters, 2025, 36(8): 110617-. doi: 10.1016/j.cclet.2024.110617
18. [18]
  Yuliang Yang , Jingyi Zhang , Yu Wang , Huan Chen , Yijian Gao , Xiliang Li , Yingpeng Wan , Qi Zhao , Ning Li , Shengliang Li . Quintuple-acceptor engineering of anti-quenching conjugated oligomers for highly efficient NIR-Ⅱb imaging and phototheranostics. Chinese Chemical Letters, 2025, 36(11): 110834-. doi: 10.1016/j.cclet.2025.110834
19. [19]
  Zhenzhong MEI , Hongyu WANG , Xiuqi KANG , Yongliang SHAO , Jinzhong GU . Syntheses and catalytic performances of three coordination polymers with tetracarboxylate ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1795-1802. doi: 10.11862/CJIC.20240081
20. [20]
  Xiangan Song , Shaogang Shen , Mengyao Lu , Ying Wang , Yong Zhang . Trifluoromethyl enable high-performance single-emitter white organic light-emitting devices based on quinazoline acceptor. Chinese Chemical Letters, 2024, 35(4): 109118-. doi: 10.1016/j.cclet.2023.109118

Get Citation

PDF

XML

Metrics

PDF Downloads(5)
Abstract views(1457)
HTML views(107)

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