Citation: Cui Jingjing. State of the Art in Germanium-Containing Aromatic Systems[J]. Chinese Journal of Organic Chemistry, ;2018, 38(11): 2888-2895. doi: 10.6023/cjoc201805049 shu

State of the Art in Germanium-Containing Aromatic Systems

Cui Jingjing ^,

School of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan 430205

Corresponding author: Cui Jingjing, 17061701@wit.edu.cn
Received Date: 26 May 2018
Revised Date: 20 June 2018
Available Online: 5 November 2018
Fund Project: Project supported by the Knowledge Innovation Program of Hubei Provience (Natural Science Foundation) 2018CFB347Project supported by the Knowledge Innovation Program of Hubei Provience (Natural Science Foundation) (No. 2018CFB347) and the Youths Science Foundation (No. K201832) of Wuhan Institute of Technologythe Youths Science Foundation of Wuhan Institute of Technology K201832

Figures(9)

Germanium-containing conjugated compounds are regarded as powerful candidates for the development of optoelectronic material. As a subclass of germanium-containing conjugated compounds and a crucial type of the heavy analogues of aromatic compounds, germanium-containing aromatic hydrocarbons (Ge-AHs) have attracted much attention and developed rapidly in recent days. According to the charge of the Ge-AHs, these species were categorized into three subclasses:neutral, anionic and cationic species. Herein, the synthetic methodology together with the reactivity of these reported Ge-AHs is summarized and the parameters used for the evaluation of the aromaticity of these compounds is highlighted. Ge-AHs and aromatic hydrocarbons share similar structural and magnetic properties. However, their major reactivity is quite different. This review will not only inspire the discovery of new structures and reactivities of Ge-Ahs, but also help to form a deeper understanding of the concept of aromaticy.
- germanium,
- aromaticity,
- main group chemistry
1. [1]
  (a) Toal, S. J.; Trogler, W. C. J. Mater. Chem. 2006, 16, 2871.
  (b) Amb, C. M.; Chen, S.; Graham, K. R.; Subbiah, J.; Small, C. E.; So, F.; Reynolds, J. R. J. Am. Chem. Soc. 2011, 133, 10062.
  (c) Shynkaruk, O.; He, G.; McDonald, R.; Ferguson, M. J.; Rivard, E. Chem. Eur. J. 2015, 22, 248.
  (d) Lu, L.; Zheng, T.; Wu, Q.; Schneider, A. M.; Zhao, D.; Yu, L. Chem. Rev. 2015, 115, 12666.
  (e) Ohshita, J.; Miyazaki, M.; Nakashima, M.; Tanaka, D.; Ooyama, Y.; Sasaki, T.; Kunugi, Y.; Morihara, Y. RSC Adv. 2015, 5, 12686.
  (f) Parke, S. M.; Boone, M. P.; Rivard, E. Chem. Commun. 2016, 52, 9485.
2. [2]
  (a) Elliott, G. P.; Roper, W. R.; Waters, J. M. J. Chem. Soc., Chem. Commun. 1982, 811.
  (b) Zhu, C.; Li, S.; Luo, M.; Zhou, X.; Niu, Y.; Lin, M.; Zhu, J.; Cao, Z.; Lu, X.; Wen, T.; Xie, Z.; Schleyer, P. V. R.; Xia, H. Nat. Chem. 2013, 5, 698.
  (c) Cao, X.-Y.; Zhao, Q.; Lin, Z.; Xia, H. Acc. Chem. Res. 2014, 47, 341.
  (d) Roy, S.; Rosenthal, U.; Jemmis, E. D. Acc. Chem. Res. 2014, 47, 2917.
  (e) Fernandez, I.; Frenking, G.; Merino, G. Chem. Soc. Rev. 2015, 44, 6452.
  (f) Wei, J.; Zhang, Y.; Zhang, W.-X.; Xi, Z. Angew. Chem., Int. Ed. 2015, 54, 9986.
  (g) Wei, J.; Zhang, Y.; Chi, Y.; Liu, L.; Zhang, W.-X.; Xi, Z. J. Am. Chem. Soc. 2016, 138, 60.
  (h) Zhang, Y.; Wei, J.; Chi, Y.; Zhang, X.; Zhang, W.-X.; Xi, Z. J. Am. Chem. Soc. 2017, 139, 5039.
  (i) Zhang, Y.; Chi, Y.; Wei, J.; Yang, Q.; Yang, Z.; Chen, H.; Yang, R.; Zhang, W.-X.; Xi, Z. Organometallics 2017, 36, 2982.
  (j) Frogley, B. J.; Wright, L. J. Chem. Eur. J. 2018, 24, 2025.
3. [3]
  (a) Lee, V. Y.; Sekiguchi, A. Chem. Soc. Rev. 2008, 37, 1652.
  (b) Lee, V. Y.; Sekiguchi, A. In Organometallic Compounds of Low-Coordinate Si, Ge, Sn and Pb, John Wiley & Sons, Ltd, 2010, p. 335.
  (c) Tokitoh, N.; Inamura, K.; Mizuhata, Y. Phosphorus Sulfur Silicon Relat. Elem. 2011, 186, 1323.
  (d) Wei, J.; Zhang, W.-X.; Xi, Z. Chem. Sci. 2018, 9, 560.
  (e) Saito, M. Acc. Chem. Res. 2018, 51, 160.
4. [4]
  Hua, Y. H.; Zhang, H.; Xia, H. P. Chin. J. Org. Chem. 2018, 38, 11(in Chinese).
5. [5]
  Izawa, M.; Kim, T.; Ishida, S. i.; Tanaka, T.; Mori, T.; Kim, D.; Osuka, A. Angew. Chem., Int. Ed. 2017, 56, 3982. doi: 10.1002/anie.201700063
6. [6]
  Märkl, G.; Rudnick, D. Tetrahedron Lett. 1980, 21, 1405. doi: 10.1016/S0040-4039(00)92731-X
7. [7]
  Märkl, G.; Rudnick, D.; Schulz, R.; Schweig, A. Angew. Chem., Int. Ed. 1982, 21, 221.
8. [8]
  Nakata, N.; Takeda, N.; Tokitoh, N. Organometallics 2001, 20, 5507. doi: 10.1021/om010881y
9. [9]
  Mizuhata, Y.; Sasamori, T.; Nagahora, N.; Watanabe, Y.; Furukawa, Y.; Tokitoh, N. Dalton Trans. 2008, 4409.
10. [10]
  (a) Nakata, N.; Takeda, N.; Tokitoh, N. J. Am. Chem. Soc. 2002, 124, 6914.
  (b) Nakata, N.; Takeda, N.; Tokitoh, N. J. Organomet. Chem. 2003, 672, 66.
11. [11]
  Sasamori, T.; Inamura, K.; Hoshino, W.; Nakata, N.; Mizuhata, Y.; Watanabe, Y.; Furukawa, Y.; Tokitoh, N. Organometallics 2006, 25, 3533. doi: 10.1021/om060371+
12. [12]
  Tokitoh, N. Acc. Chem. Res. 2004, 37, 86. doi: 10.1021/ar020093k
13. [13]
  (a) Tokitoh, N.; Nakata, N.; Shinohara, A.; Takeda, N.; Sasamori, T. Chem. Eur. J. 2007, 13, 1856.
  (b) Mizuhata, Y.; Inamura, K.; Tokitoh, N. Can. J. Chem. 2014, 92, 441.
14. [14]
  (a) Nakata, N.; Takeda, N.; Tokitoh, N. Chem. Lett. 2002, 31, 818.
  (b) Nakata, N.; Takeda, N.; Tokitoh, N. Angew. Chem., Int. Ed. 2003, 42, 115.
15. [15]
  Nakata, N.; Takeda, N.; Tokitoh, N. Organometallics 2003, 22, 481. doi: 10.1021/om020879m
16. [16]
  (a) Sasamori, T.; Sugahara, T.; Agou, T.; Guo, J.-D.; Nagase, S.; Streubel, R.; Tokitoh, N. Organometallics 2015, 34, 2106.
  (b) Sugahara, T.; Guo, J.-D.; Sasamori, T.; Karatsu, Y.; Furukawa, Y.; Ferao, A. E.; Nagase, S.; Tokitoh, N. Bull. Chem. Soc. Jpn. 2016, 89, 1375.
17. [17]
  Sugahara, T.; Guo, J. D.; Sasamori, T.; Nagase, S.; Tokitoh, N. Angew. Chem., Int. Ed. 2018, 57, 3499. doi: 10.1002/anie.201801222
18. [18]
  Boehme, C.; Frenking, G. J. Am. Chem. Soc. 1996, 118, 2039. doi: 10.1021/ja9527075
19. [19]
  Tuononen, H. M.; Roesler, R.; Dutton, J. L.; Ragogna, P. J. Inorg. Chem. 2007, 46, 10693. doi: 10.1021/ic701350e
20. [20]
  Leites, L. A.; Bukalov, S. S.; Aysin, R. R.; Piskunov, A. V.; Chegerev, M. G.; Cherkasov, V. K.; Zabula, A. V.; West, R. Organometallics 2015, 34, 2278. doi: 10.1021/om501054t
21. [21]
  Meller, A.; Pfeiffer, J.; Noltemeyer, M. Z. Anorg. Allg. Chem. 1989, 572, 145. doi: 10.1002/(ISSN)1521-3749
22. [22]
  Herrmann, W. A.; Denk, M.; Behm, J.; Scherer, W.; Klingan, F. R.; Bock, H.; Solouki, B.; Wagner, M. Angew. Chem., Int. Ed. 1992, 31, 1485. doi: 10.1002/(ISSN)1521-3773
23. [23]
  Allen, F. H.; Kennard, O.; Watson, D. G.; Brammer, L.; Orpen, A. G.; Taylor, R. J. Chem. Soc., Perkin Trans. 2 1987, S1
24. [24]
  Leites, L. A.; Bukalov, S. S.; Zabula, A. V.; Garbuzova, I. A.; Moser, D. F.; West, R. J. Am. Chem. Soc. 2004, 126, 4114. doi: 10.1021/ja0317877
25. [25]
  Guha, A. K.; Sarmah, S.; Phukan, A. K. Dalton Trans. 2010, 39, 7374. doi: 10.1039/c003266b
26. [26]
  (a) Aysin, R. R.; Leites, L. A.; Bukalov, S. S.; Zabula, A. V.; West, R. Inorg. Chem. 2016, 55, 4698.
  (b) Aysin, R. R.; Bukalov, S. S.; Leites, L. A.; Zabula, A. V. Dalton Trans. 2017, 46, 8774.
27. [27]
  Kühl, O.; L nnecke, P.; Heinicke, J. Inorg. Chem. 2003, 42, 2836. doi: 10.1021/ic0259991
28. [28]
  Blom, B.; Said, A.; Szilvási, T.; Menezes, P. W.; Tan, G.; Baumgartner, J.; Driess, M. Inorg. Chem. 2015, 54, 8840. doi: 10.1021/acs.inorgchem.5b01643
29. [29]
  Tumanskii, B.; Pine, P.; Apeloig, Y.; Hill, N. J.; West, R. J. Am. Chem. Soc. 2005, 127, 8248. doi: 10.1021/ja051169l
30. [30]
  Naka, A.; Hill, N. J.; West, R. Organometallics 2004, 23, 6330. doi: 10.1021/om049233f
31. [31]
  Su, B.; Ganguly, R.; Li, Y.; Kinjo, R. Angew. Chem., Int. Ed. 2014, 53, 13106. doi: 10.1002/anie.201406930
32. [32]
  Su, B.; Ganguly, R.; Li, Y.; Kinjo, R. Chem. Commun. 2016, 52, 613. doi: 10.1039/C5CC08665E
33. [33]
  Freeman, W. P.; Tilley, T. D.; Rheingold, A. L.; Ostrander, R. L.; Angew. Chem., Int. Ed. Engl. 1993, 32, 1744. doi: 10.1002/(ISSN)1521-3773
34. [34]
  Freeman, W. P.; Tilley, T. D.; LiableSands, L. M.; Rheingold, A. L. J. Am. Chem. Soc. 1996, 118, 10457. doi: 10.1021/ja962103g
35. [35]
  Goldfuss, B.; Schleyer, P. V. R. Organometallics 1997, 16, 1543. doi: 10.1021/om960994v
36. [36]
  Freeman, W. P.; Tilley, T. D.; Rheingold, A. L.; Ostrander, R. L. Angew. Chem., Int. Ed. 1993, 32, 1744. doi: 10.1002/(ISSN)1521-3773
37. [37]
  Dysard, J. M.; Tilley, T. D. J. Am. Chem. Soc. 2000, 122, 3097. doi: 10.1021/ja993563n
38. [38]
  (a) Dysard, J. M.; Tilley, T. D. J. Am. Chem. Soc. 1998, 120, 8245. (b) Freeman, W. P.; Dysard, J. M.; Tilley, T. D.; Rheingold, A. L. Organometallics 2002, 21, 1734.
39. [39]
  Dysard, J. M.; Tilley, T. D. Organometallics 2000, 19, 2671. doi: 10.1021/om000220l
40. [40]
  (a) Lee, V. Y.; Kato, R.; Ichinohe, M.; Sekiguchi, A. J. Am. Chem. Soc. 2005, 127, 13142.
  (b) Lee, V. Y.; Takanashi, K.; Kato, R.; Matsuno, T.; Ichinohe, M.; Sekiguchi, A. J. Organomet. Chem. 2007, 692, 2800.
41. [41]
  (a) Lee, V. Y.; Kato, R.; Sekiguchi, A.; Krapp, A.; Frenking, G. J. Am. Chem. Soc. 2007, 129, 10340.
  (b) Lee, V. Y.; Kato, R.; Sekiguchi, A. Bull. Chem. Soc. Jpn. 2013, 86, 1466.
42. [42]
  West, R.; Sohn, H.; Powell, D. R.; Müller, T.; Apeloig, Y. Angew. Chem., Int. Ed. 1996, 35, 1002. doi: 10.1002/(ISSN)1521-3773
43. [43]
  Choi, S.-B.; Boudjouk, P.; Qin, K. Organometallics 2000, 19, 1806. doi: 10.1021/om990991t
44. [44]
  Liu, Y. X.; Ballweg, D.; Muller, T.; Guzei, I. A.; Clark, R. W.; West, R. J. Am. Chem. Soc. 2002, 124, 12174. doi: 10.1021/ja020267t
45. [45]
  Wang, W.; Yao, S.; van Wüllen, C.; Driess, M. J. Am. Chem. Soc. 2008, 130, 9640. doi: 10.1021/ja802502b
46. [46]
  Driess, M.; Woodul, W. D.; Richards, A. F.; Stasch, A.; Jones, C. Organometallics 2010, 29, 3655. doi: 10.1021/om100595a
47. [47]
  Wang, W.; Inoue, S.; Yao, S.; Driess, M. Chem. Commun. 2009, 2661.
48. [48]
  Mizuhata, Y.; Fujimori, S.; Sasamori, T.; Tokitoh, N. Angew. Chem., Int. Ed. 2017, 56, 4588. doi: 10.1002/anie.201700801
49. [49]
  (a) Sekiguchi, A.; Tsukamoto, M.; Ichinohe, M.; Fukaya, N. Phosphorus, Sulfur, Silicon Relat. Elem. 1997, 124, 323.
  (b) Sekiguchi, A.; Tsukamoto, M.; Ichinohe, M. Science 1997, 275, 60.
50. [50]
  (a) Sekiguchi, A.; Fukaya, N.; Ichinohe, M.; Takagi, N.; Nagase, S. J. Am. Chem. Soc. 1999, 121, 11587.
  (b) Sekiguchi, A.; Ishida, Y.; Fukaya, N.; Ichinohe, M.; Takagi, N.; Nagase, S. J. Am. Chem. Soc. 2002, 124, 1158.
51. [51]
  Sekiguchi, A.; Ishida, Y.; Kabe, Y.; Ichinohe, M. J. Am. Chem. Soc. 2002, 124, 8776. doi: 10.1021/ja020395h
52. [52]
  Ishida, Y.; Sekiguchi, A.; Kabe, Y. J. Am. Chem. Soc. 2003, 125, 11468. doi: 10.1021/ja030327a
53. [53]
  Fukaya, N.; Ichinohe, M.; Sekiguchi, A. Angew. Chem., Int. Ed. 2000, 39, 3881. doi: 10.1002/(ISSN)1521-3773
54. [54]
  Stender, M.; Phillips, A. D.; Power, P. P. Inorg. Chem. 2001, 40, 5314. doi: 10.1021/ic0155582
55. [55]
  Driess, M.; Yao, S.; Brym, M.; Wüllen, C. V. Angew. Chem., Int. Ed. 2006, 45, 4349. doi: 10.1002/(ISSN)1521-3773
1. [1]
  Shikun Jia , Hui Jiang , Yuanyuan Chang , Linlin Shi , Erqing Li , Kai Li , Xinqi Hao , Guangjian Mei . 大学有机化学“芳香性”教学拓展——以芳香全氮化合物为例. University Chemistry, 2026, 41(10): 127-131. doi: 10.12461/PKU.DXHX202511012
2. [2]
  Yonghui Wang , Weilin Chen , Yangguang Li . Knowledge Construction of “Solubility of Inorganic Substances” in Elemental Chemistry Teaching. University Chemistry, 2024, 39(4): 261-267. doi: 10.3866/PKU.DXHX202312102
3. [3]
  Xiangli Wang , Yuanfu Deng . Teaching Design of Elemental Chemistry from the Perspective of “Curriculum Ideology and Politics”: Taking Arsenic as an Example. University Chemistry, 2024, 39(2): 270-279. doi: 10.3866/PKU.DXHX202308092
4. [4]
  Gaihua Li , Donglian Liu , Xiuge Wang , Shuang Liu , Ning Zhang , Xuerui Tian . Teaching Design of Elemental Chemistry under the Concept of “Curriculum Ideology and Politics”: a Case of Mercury. University Chemistry, 2026, 41(2): 45-53. doi: 10.12461/PKU.DXHX202502025
5. [5]
  Yanyang Han , Shanshan Liu , Tao He , Kai Feng , Xin Yang , Qingzhong Li , Tao Zhang . AI助教在无机元素化学教学中的应用. University Chemistry, 2026, 41(8): 111-118. doi: 10.12461/PKU.DXHX202507097
6. [6]
  Peiyan Ma , Zheng Xie , Chen Wang . “元素周期表与元素性质的周期性变化”的线上线下混合式教学模式课程设计. University Chemistry, 2026, 41(8): 8-18. doi: 10.12461/PKU.DXHX202508015
7. [7]
  Siyao Zhan , Yajiao Wang , Zhihuan Cai , Ayizhada Maimaitiyumier , Tilan Duan , Xiangfeng Wei , Qi Wang , Jiehua Liu , Xianghua Kong . Exploration of the Chemical Elements across Time and Space. University Chemistry, 2024, 39(9): 5-10. doi: 10.12461/PKU.DXHX202403071
8. [8]
  Xiaohang Qiu . Suggestions for s-block elements teaching in the inorganic chemistry course of the Chemistry “101 Plan”. University Chemistry, 2026, 41(6): 13-17. doi: 10.12461/PKU.DXHX202510027
9. [9]
  Jiaqi AN , Yunle LIU , Jianxuan SHANG , Yan GUO , Ce LIU , Fanlong ZENG , Anyang LI , Wenyuan WANG . Reactivity of extremely bulky silylaminogermylene chloride and bonding analysis of a cubic tetragermylene. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1511-1518. doi: 10.11862/CJIC.20240072
10. [10]
  Huan Zhang , Linyu Pu , Wei Wang , Yatang Dai , Xu Huang . Curriculum Development and Blended Teaching Practice in the Graduate Course on Elemental Inorganic Chemistry. University Chemistry, 2024, 39(6): 166-173. doi: 10.3866/PKU.DXHX202402010
11. [11]
  Zhengli Hu , Jia Wang , Yi-Lun Ying , Shaochuang Liu , Hui Ma , Wenwei Zhang , Jianrong Zhang , Yi-Tao Long . Exploration of Ideological and Political Elements in the Development History of Nanopore Electrochemistry. University Chemistry, 2024, 39(8): 344-350. doi: 10.3866/PKU.DXHX202401072
12. [12]
  Yang Lv , Yingping Jia , Yanhua Li , Hexiang Zhong , Xinping Wang . Integrating the Ideological Elements with the “Chemical Reaction Heat” Teaching. University Chemistry, 2024, 39(11): 44-51. doi: 10.12461/PKU.DXHX202402059
13. [13]
  Ying Wang , Quanguo Zhai , Zhiqiang Wang , Qingjuan Lei , Shengli Gao . 无机化学中“碱金属元素”教学内容的重构. University Chemistry, 2025, 40(6): 85-92. doi: 10.12461/PKU.DXHX202407049
14. [14]
  Ran Cui , Zhi-Ling Zhang , Yanling Liu . Teaching Reform Exploration in “Analytical Chemistry” Course with Ideological and Political Elements Integration. University Chemistry, 2026, 41(4): 60-66. doi: 10.12461/PKU.DXHX202506052
15. [15]
  Daxiang Gui , Hui Li . The dual-faced envoy of the elemental world. University Chemistry, 2026, 41(4): 317-323. doi: 10.12461/PKU.DXHX202502098
16. [16]
  Yajun Jian , Quanguo Zhai , Quan Gu , Shengli Gao . Reconstruction and Practice of the Teaching Content of “Carbon Group Elements” in Inorganic Chemistry to Reflect Comprehensive Education Function. University Chemistry, 2024, 39(11): 96-107. doi: 10.12461/PKU.DXHX202403006
17. [17]
  Mingbao Liu , Tian Zhang , Heng Liu , Baoyue Cao , Chengfang Qiao . ds区元素电子结构赋予的特殊物理化学性质及生理作用. University Chemistry, 2026, 41(8): 176-193. doi: 10.12461/PKU.DXHX202507120
18. [18]
  Yuheng Zhou . 大学课堂的色彩——探索过渡元素的美. University Chemistry, 2025, 40(6): 303-309. doi: 10.12461/PKU.DXHX202407110
19. [19]
  Zisu Fang , Shida Hou , Yuxuan Gong , Jing Yan , Rui Bian , Dingwen Wang , Yi Yan . Defending the Zirconium Kingdom: An Elemental Adventure. University Chemistry, 2026, 41(2): 323-327. doi: 10.12461/PKU.DXHX202503071
20. [20]
  Yanhui Sun , Junmin Nan , Guozheng Ma , Xiaoxi Zuo , Guoliang Li , Xiaoming Lin . Exploration and Teaching Practice of Ideological and Political Elements in Interface Physical Chemistry: Taking “Additional Pressure on Curved Surfaces” as an Teaching Example. University Chemistry, 2024, 39(11): 20-27. doi: 10.3866/PKU.DXHX202402023

Get Citation

PDF

XML

Metrics

PDF Downloads(34)
Abstract views(3645)
HTML views(509)

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