Citation: Gaozhang Gou, Zhaoling Zhang, Tao Fan, Lei Fang, Mingxian Liu, Liangchun Li. Synthesis, optical properties and self-organization of blue-emitting butterfly-shaped dithienobenzosiloles[J]. Chinese Chemical Letters, ;2022, 33(9): 4306-4312. doi: 10.1016/j.cclet.2021.12.052 shu

Synthesis, optical properties and self-organization of blue-emitting butterfly-shaped dithienobenzosiloles

Shanghai Key Lab of Chemical Assessment and Sustainability, School of Chemical Science and Engineering, Tongji University, Shanghai 200092, China

lilc@tongji.edu.cn

Received Date: 23 October 2021
Revised Date: 17 December 2021
Accepted Date: 22 December 2021
Available Online: 26 December 2021

Figures(7)

Ten novel butterfly-shaped dithienobenzosilole-based luminogens, which are peripherally installed with a variety of substituents including hydrogen, phenyl and substituted phenyl groups, have been readily prepared via an iodine-induced intramolecular electrophilic double-cyclisation reaction and subsequent deiodination or coupling reactions. The optical and electrochemical properties of these compounds were systematically investigated to clarify the relationships between their structures and properties, supported by theoretical calculations. These compounds exhibit deep-blue to sky-blue emissions and high photoluminescence quantum yields up to 0.84 in solution and solid states which are regulated by the functional blades and their steric hindrance on the α– and β–positions of thiophene rings. Their high thermal- and photo- stabilities have been revealed and mainly attributed to the dithienobenzosilole core.
- Dithienobenzosilole,
- Luminogen,
- Double-cyclisation,
- Blue-emitting,
- Photo-stability
1. [1]
  E.J.W. List, R. Guentner, P. Scanducci de Freitas, U. Scherf, Adv. Mater. 14 (2002) 374–378. doi: 10.1002/1521-4095(20020304)14:5<374::AID-ADMA374>3.0.CO;2-U
2. [2]
  L. Romaner, A. Pogantsch, P. Scandiucci de Freitas, et al., Adv. Funct. Mater. 13 (2003) 597–601. doi: 10.1002/adfm.200304360
3. [3]
  K.L. Chan, M.J. McKiernan, C.R. Towns, A.B. Holmes, J. Am. Chem. Soc. 127 (2005) 7662–7663. doi: 10.1021/ja0508065
4. [4]
  M. Shimizu, Chem. Rec. 15 (2015) 73–85. doi: 10.1002/tcr.201402084
5. [5]
  T.T. Dang, H.M.T. Nguyen, H. Nguyen, et al., Molecules 25 (2020) 548. doi: 10.3390/molecules25030548
6. [6]
  J. Sołoducho, D. Zając, K. Spychalska, S. Baluta, J. Cabaj, Molecules 26 (2021) 2012. doi: 10.3390/molecules26072012
7. [7]
  L. Li, J. Xiang, C. Xu, Org. Lett. 9 (2007) 4877–4879. doi: 10.1021/ol702215m
8. [8]
  I. McCulloch, R.S. Ashraf, L. Biniek, et al., Acc. Chem. Res. 45 (2012) 714–722. doi: 10.1021/ar200208g
9. [9]
  M. Brook, Silicon in Organic, Organometallic, and Polymer Chemistry, Wiley, New York, 1999.
10. [10]
  Q. Yang, L.C. Li, S.H. Li, D.M. Yue, C.H. Xu, Chin. Chem. Lett. 23 (2012) 1303–1306. doi: 10.1016/j.cclet.2012.09.017
11. [11]
  Q. Li, Z. Li, Adv. Sci. 4 (2017) 1600484. doi: 10.1002/advs.201600484
12. [12]
  W. Feng, Q. Su, Y. Ma, et al., J. Org. Chem. 85 (2020) 158–167. doi: 10.1021/acs.joc.9b02383
13. [13]
  K. Mouri, A. Wakamiya, H. Yamada, T. Kajiwara, S. Yamaguchi, Org. Lett. 9 (2007) 93–96. doi: 10.1021/ol062615s
14. [14]
  C. Xu, A. Wakamiya, S. Yamaguchi, J. Am. Chem. Soc. 127 (2005) 1638–1639. doi: 10.1021/ja042964m
15. [15]
  S. Yamaguchi, C. Xu, K. Tamao, J. Am. Chem. Soc. 125 (2003) 13662–13663. doi: 10.1021/ja038487+
16. [16]
  S. Beaupré, P.L.T. Boudreault, M. Leclerc, Adv. Mater. 22 (2010) E6–E27. doi: 10.1002/adma.200903484
17. [17]
  R.F. Chen, L.Y. Liu, H. Fu, et al., J. Phys. Chem. B 115 (2011) 242–248. doi: 10.1021/jp108476x
18. [18]
  S. Furukawa, J. Kobayashi, T. Kawashima, J. Am. Chem. Soc. 131 (2009) 14192–14193. doi: 10.1021/ja906566r
19. [19]
  S. Chen, D. Mu, P.L. Mai, et al., Nat. Commun. 12 (2021) 1249. doi: 10.1038/s41467-021-21489-6
20. [20]
  J. Zhu, S. Chen, C. He, J. Am. Chem. Soc. 143 (2021) 5301–5307. doi: 10.1021/jacs.1c01106
21. [21]
  H. Feng, Z. Zhou, A.K. May, et al., J. Mater. Chem. C 9 (2021) 6470–6476. doi: 10.1039/D1TC01488A
22. [22]
  Y. Zheng, Z. Wang, X. Wang, et al., ACS Appl. Electron. Mater. 3 (2021) 422–429. doi: 10.1021/acsaelm.0c00960
23. [23]
  M. Onoe, K. Baba, Y. Kim, et al., J. Am. Chem. Soc. 134 (2012) 19477–19488. doi: 10.1021/ja3096174
24. [24]
  D. Leifert, A. Studer, Org. Lett. 17 (2015) 386–389. doi: 10.1021/ol503574k
25. [25]
  Y. Dong, Y. Takata, Y. Yoshigoe, K. Sekine, Y. Kuninobu, Chem. Commun. 55 (2019) 13303–13306. doi: 10.1039/C9CC07692A
26. [26]
  S. Furukawa, J. Kobayashi, T. Kawashima, Dalton Trans. 39 (2010) 9329–9336. doi: 10.1039/c0dt00136h
27. [27]
  T. Ureshino, T. Yoshida, Y. Kuninobu, K. Takai, J. Am. Chem. Soc. 132 (2010) 14324–14326. doi: 10.1021/ja107698p
28. [28]
  X. Zhang, J. Fang, C. Cai, G. Lu, Chin. Chem. Lett. 32 (2021) 1280–1292. doi: 10.1016/j.cclet.2020.09.058
29. [29]
  Y. Yabusaki, N. Ohshima, H. Kondo, et al., Chem. Eur. J. 16 (2010) 5581–5585. doi: 10.1002/chem.200903408
30. [30]
  C. Yang, J. Wang, J. Li, et al., Adv. Synth. Catal. 360 (2018) 3049–3054. doi: 10.1002/adsc.201800417
31. [31]
  H. Yao, L. Ye, H. Zhang, et al., Chem. Rev. 116 (2016) 7397–7457. doi: 10.1021/acs.chemrev.6b00176
32. [32]
  D.M. Stoltzfus, J.E. Donaghey, A. Armin, et al., Chem. Rev. 116 (2016) 12920–12955. doi: 10.1021/acs.chemrev.6b00126
33. [33]
  Z. Genene, W. Mammo, E. Wang, M.R. Andersson, Adv. Mater. 31 (2019) 1807275. doi: 10.1002/adma.201807275
34. [34]
  A. Molina-Ontoria, I. Zimmermann, I. Garcia-Benito, et al., Angew. Chem. 128 (2016) 6378–6382. doi: 10.1002/ange.201511877
35. [35]
  J. Guo, S. Hu, W. Luo, et al., Chem. Commun. 53 (2017) 1463–1466. doi: 10.1039/C6CC09892D
36. [36]
  J. Wang, Y. He, S. Guo, et al., ACS Appl. Mater. Interfaces 13 (2021) 12250–12258. doi: 10.1021/acsami.0c21286
37. [37]
  Y. Xu, Q. Ji, L. Yin, et al., ACS Appl. Mater. Interfaces 13 (2021) 23993–24004. doi: 10.1021/acsami.1c03794
38. [38]
  A. Gupta, B.L. Flynn, Org. Lett. 19 (2017) 1939–1941. doi: 10.1021/acs.orglett.7b00265
39. [39]
  D. Zhang, J. Cai, J. Du, et al., J. Org. Chem. 86 (2021) 2593–2601. doi: 10.1021/acs.joc.0c02679
40. [40]
  T. Kitamura, K. Morita, H. Nakamori, S. Bräse, I.A. Balova, J. Org. Chem. 84 (2019) 4191–4199. doi: 10.1021/acs.joc.9b00213
41. [41]
  C.H. Lee, Y.Y. Lai, J.Y. Hsu, P.K. Huang, Y.J. Cheng, Chem. Sci. 8 (2017) 2942–2951. doi: 10.1039/C6SC04129A
42. [42]
  C.H. Lee, Y.Y. Lai, S.W. Cheng, Y.J. Cheng, Org. Lett. 16 (2014) 936–939. doi: 10.1021/ol4036787
43. [43]
  L. Li, C. Xu, S. Li, Tetrahedron Lett. 51 (2010) 622–624. doi: 10.1016/j.tetlet.2009.11.074
44. [44]
  G. Gou, Z. Zhang, B. Yuan, T. Fan, L. Li, Dyes Pigments 194 (2021) 109642. doi: 10.1016/j.dyepig.2021.109642
45. [45]
  L. Li, S. Li, C.H. Zhao, C. Xu, Eur. J. Inorg. Chem. 2014 (2014) 1880–1885. doi: 10.1002/ejic.201400061
46. [46]
  E. Wang, C. Li, W. Zhuang, J. Peng, Y. Cao, J. Mater. Chem. 18 (2008) 797–801. doi: 10.1039/b716607a
47. [47]
  E. Pusztai, I.S. Toulokhonova, N. Temple, et al., Organometallics 32 (2013) 2529–2535. doi: 10.1021/om300891n
48. [48]
  R. Volpe, L. Aurelio, M.G. Gillin, E.H. Krenske, B.L. Flynn, Chem. Eur. J. 21 (2015) 10191–10199. doi: 10.1002/chem.201500384
49. [49]
  S. Mehta, J.P. Waldo, R.C. Larock, J. Org. Chem. 74 (2009) 1141–1147. doi: 10.1021/jo802196r
50. [50]
  H. Zhang, Z. Zhao, P.R. McGonigal, et al., Mater. Today 32 (2020) 275–292. doi: 10.1016/j.mattod.2019.08.010
51. [51]
  J. Luo, Z. Xie, J.W.Y. Lam, et al., Chem. Commun. (2001) 1740–1741.
52. [52]
  Y. Xiong, J. Zeng, B. Chen, et al., Chin. Chem. Lett. 30 (2019) 592–596. doi: 10.1016/j.cclet.2018.12.020
53. [53]
  L. Sun, N. Sun, L. Bai, et al., Chin. Chem. Lett. 30 (2019) 1959–1964. doi: 10.1016/j.cclet.2019.08.048
54. [54]
  Y. Wang, J. Nie, W. Fang, et al., Chem. Rev. 120 (2020) 4534–4577. doi: 10.1021/acs.chemrev.9b00814
55. [55]
  Z. Zhao, H. Zhang, J.W.Y. Lam, B.Z. Tang, Angew. Chem. Int. Ed. 59 (2020) 9888–9907. doi: 10.1002/anie.201916729
56. [56]
  P. Meti, J.W. Yang, Y.D. Gong, Dyes Pigments 192 (2021) 109419. doi: 10.1016/j.dyepig.2021.109419
57. [57]
  N.G. Connelly, W.E. Geiger, Chem. Rev. 96 (1996) 877–910. doi: 10.1021/cr940053x
58. [58]
  M. Shimizu, K. Mochida, M. Katoh, T. Hiyama, J. Phys. Chem. C 114 (2010) 10004–10014. doi: 10.1021/jp103410x
59. [59]
  M.J. Frisch, G.W. Trucks, H.B. Schlegel, et al., Gaussian 09, Revision B. 01, Gaussian, Inc, Wallingford CT, 2010.
60. [60]
  S.H. Lee, B.B. Jang, Z.H. Kafafi, J. Am. Chem. Soc. 127 (2005) 9071–9078. doi: 10.1021/ja042762q
61. [61]
  Z. Zhou, Q. Liu, X. Chen, et al., Adv. Funct. Mater. 31 (2021) 2009024. doi: 10.1002/adfm.202009024
62. [62]
  Z. Zhou, S. Xie, X. Chen, et al., J. Am. Chem. Soc. 141 (2019) 9803–9807. doi: 10.1021/jacs.9b04426
63. [63]
  X. Gu, E. Zhao, J.W.Y. Lam, et al., Adv. Mater. 27 (2015) 7093–7100. doi: 10.1002/adma.201503751
64. [64]
  W. Li, C. Jiao, X. Li, et al., Angew. Chem. Int. Ed. 53 (2014) 4603–4607. doi: 10.1002/anie.201310438
65. [65]
  X. Wu, W. Zhu, Chem. Soc. Rev. 44 (2015) 4179–4184. doi: 10.1039/C4CS00152D
66. [66]
  Q. Zheng, L.D. Lavis, Curr. Opin. Chem. Biol. 39 (2017) 32–38. doi: 10.1016/j.cbpa.2017.04.017
1. [1]
  Bin Dong , Ning Yu , Qiu-Yue Wang , Jing-Ke Ren , Xin-Yu Zhang , Zhi-Jie Zhang , Ruo-Yao Fan , Da-Peng Liu , Yong-Ming Chai . Double active sites promoting hydrogen evolution activity and stability of CoRuOH/Co₂P by rapid hydrolysis. Chinese Chemical Letters, 2024, 35(7): 109221-. doi: 10.1016/j.cclet.2023.109221
2. [2]
  Yuan Liu , Boyang Wang , Yaxin Li , Weidong Li , Siyu Lu . Understanding excitonic behavior and electroluminescence light emitting diode application of carbon dots. Chinese Chemical Letters, 2025, 36(2): 110426-. doi: 10.1016/j.cclet.2024.110426
3. [3]
  Yu He , Hao Jiang , Shaoxuan Yuan , Jiayi Lu , Qiang Sun . On-surface photo-induced dechlorination. Chinese Chemical Letters, 2024, 35(9): 109807-. doi: 10.1016/j.cclet.2024.109807
4. [4]
  Hui Liu , Xiangyang Tang , Zhuang Cheng , Yin Hu , Yan Yan , Yangze Xu , Zihan Su , Futong Liu , Ping Lu . Constructing multifunctional deep-blue emitters with weak charge transfer excited state for high-performance non-doped blue OLEDs and single-emissive-layer hybrid white OLEDs. Chinese Chemical Letters, 2024, 35(10): 109809-. doi: 10.1016/j.cclet.2024.109809
5. [5]
  Rui Cheng , Tingting Zhang , Xin Huang , Jian Yu . Facile synthesis of high-brightness green-emitting carbon dots with narrow bandwidth towards backlight display. Chinese Chemical Letters, 2024, 35(5): 108763-. doi: 10.1016/j.cclet.2023.108763
6. [6]
  Jiayu Xu , Meng Li , Baoxia Dong , Ligang Feng . Fully fluorinated hybrid zeolite imidazole/Prussian blue analogs with combined advantages for efficient oxygen evolution reaction. Chinese Chemical Letters, 2024, 35(6): 108798-. doi: 10.1016/j.cclet.2023.108798
7. [7]
  Pingping Wang , Huixian Miao , Kechuan Sheng , Bin Wang , Fan Feng , Xuankun Cai , Wei Huang , Dayu Wu . Efficient blue-light-excitable copper(Ⅰ) coordination network phosphors for high-performance white LEDs. Chinese Chemical Letters, 2024, 35(4): 108600-. doi: 10.1016/j.cclet.2023.108600
8. [8]
  Yanrui Liu , Paramaguru Ganesan , Peng Gao . Harnessing d-f transition rare earth complexes for single layer white organic light emitting diodes. Chinese Journal of Structural Chemistry, 2024, 43(9): 100369-100369. doi: 10.1016/j.cjsc.2024.100369
9. [9]
  Liwen Wang , Boyang Wang , Siyu Lu , Shubo Lv , Xiaoli Qu . High quantum yield yellow emission carbon dots for the construction of blue light blocking films. Chinese Chemical Letters, 2025, 36(2): 110497-. doi: 10.1016/j.cclet.2024.110497
10. [10]
  Hailong He , Wenbing Wang , Wenmin Pang , Chen Zou , Dan Peng . Double stimulus-responsive palladium catalysts for ethylene polymerization and copolymerization. Chinese Chemical Letters, 2024, 35(7): 109534-. doi: 10.1016/j.cclet.2024.109534
11. [11]
  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
12. [12]
  Xinzhi Ding , Chong Liu , Jing Niu , Nan Chen , Shutao Xu , Yingxu Wei , Zhongmin Liu . Solid-state NMR study of the stability of MOR framework aluminum. Chinese Journal of Structural Chemistry, 2024, 43(4): 100247-100247. doi: 10.1016/j.cjsc.2024.100247
13. [13]
  Jingyuan Yang , Xinyu Tian , Liuzhong Yuan , Yu Liu , Yue Wang , Chuandong Dou . Enhancing stability of diradical polycyclic hydrocarbons via P=O-attaching. Chinese Chemical Letters, 2024, 35(8): 109745-. doi: 10.1016/j.cclet.2024.109745
14. [14]
  Ting Wang , Xin Yu , Yaqiang Xie . Unlocking stability: Preserving activity of biomimetic catalysts with covalent organic framework cladding. Chinese Chemical Letters, 2024, 35(6): 109320-. doi: 10.1016/j.cclet.2023.109320
15. [15]
  Tao LIU , Yuting TIAN , Ke GAO , Xuwei HAN , Ru'nan MIN , Wenjing ZHAO , Xueyi SUN , Caixia YIN . A photothermal agent with high photothermal conversion efficiency and high stability for tumor therapy. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1622-1632. doi: 10.11862/CJIC.20240107
16. [16]
  Zhengzhong Zhu , Shaojun Hu , Zhi Liu , Lipeng Zhou , Chongbin Tian , Qingfu Sun . A cationic radical lanthanide organic tetrahedron with remarkable coordination enhanced radical stability. Chinese Chemical Letters, 2025, 36(2): 109641-. doi: 10.1016/j.cclet.2024.109641
17. [17]
  Yanbing Shen , Yuan Yuan , Yaxin Wang , Xiaonan Ma , Wensheng Yang , Yulan Chen . Dihydroanthracene bridged bis-naphthopyrans: A multimodal chromophore with mechano- and photo-chromic properties. Chinese Chemical Letters, 2024, 35(5): 108949-. doi: 10.1016/j.cclet.2023.108949
18. [18]
  Junying Zhang , Ruochen Li , Haihua Wang , Wenbing Kang , Xing-Dong Xu . Photo-induced tunable luminescence from an aggregated amphiphilic ethylene-pyrene derivative in aqueous media. Chinese Chemical Letters, 2024, 35(6): 109216-. doi: 10.1016/j.cclet.2023.109216
19. [19]
  Xinyue Lan , Junguang Liang , Churan Wen , Xiaolong Quan , Huimin Lin , Qinqin Xu , Peixian Chen , Guangyu Yao , Dan Zhou , Meng Yu . Photo-manipulated polyunsaturated fatty acid-doped liposomal hydrogel for flexible photoimmunotherapy. Chinese Chemical Letters, 2024, 35(4): 108616-. doi: 10.1016/j.cclet.2023.108616
20. [20]
  Yulin Mao , Jingyu Ma , Jiecheng Ji , Yuliang Wang , Wanhua Wu , Cheng Yang . Crown aldoxime ethers: Their synthesis, structure, acid-catalyzed/photo-induced isomerization and adjustable guest binding. Chinese Chemical Letters, 2024, 35(11): 109927-. doi: 10.1016/j.cclet.2024.109927

Get Citation

PDF

XML

Metrics

PDF Downloads(2)
Abstract views(524)
HTML views(38)

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