Citation: Baolei Huang, Hao Sun, Xinye Li, Yuting Fan, Tao Tao. 芳香性概念的最新进展[J]. University Chemistry, ;2021, 36(8): 200906. doi: 10.3866/PKU.DXHX202009060 shu

芳香性概念的最新进展

Department of Chemistry, School of Chemistry and Materials Science, Nanjing University of Information Science & Technology, Nanjing 210044, China

Corresponding author: Tao Tao, taotao@nuist.edu.cn
Received Date: 28 September 2020

芳香性是有机化学领域非常重要的概念，这一概念可追溯至1825年法拉第发现苯和1865年凯库勒提出著名的单双键交替环状结构。时至今日，芳香性的内涵与外延仍在不断扩展。目前反休克尔规则的例子不断涌现，包括莫比乌斯芳香性规则和贝尔德规则，立体芳香性、全局芳香性等新的芳香性概念逐步提出。本文重点介绍了芳香性的实验和理论判据并通过卟啉纳米环、大环多自由基、多环共轭体系等介绍几种新的芳香性体系，并阐述了未来可能的应用。
- Aromaticity,
- 3D aromaticity,
- Global aromaticity,
- Hückel’s rule,
- Baird’s rule
1. [1]
  Hofmann, A. W. Proc. R. Soc. London. 1856,8, 1.
2. [2]
  Hückel, E. Z. Phys. 1931, 70 (3), 204.
3. [3]
  Breslow, R.; Groves, J. T.; Ryan, G. J. Am. Chem. Soc. 1967, 89 (19), 5048.
4. [4]
  Baird, N. C. J. Am. Chem. Soc. 1972, 94 (14), 4941.
5. [5]
  Yuan, J.; Sun, T.; He, X.; An, K.; Zhu, J.; Zhao, L. Nat. Commun.2016, 7 (1), 11489.
6. [6]
  Cha, W. Y.; Kim, T.; Ghosh, A.; Zhang, Z.; Ke, X. S.; Ali, R.; Lynch, V. M.; Jung, J.; Kim, W.; Lee, S.; et al. Nat. Chem. 2017, 9 (12), 1243.
7. [7]
  Liu, C.; Sandoval-Salinas, M. E.; Hong, Y.; Gopalakrishna, T. Y.; Phan, H.; Aratani, N.; Herng, T. S.; Ding, J.; Yamada, H.; Kim, D.; et al. Chem. 2018, 4 (7), 1586.
8. [8]
  Nozawa, R.; Kim, J.; Oh, J.; Lamping, A.; Wang, Y.; Shimizu, S.; Hisaki, I.; Kowalczyk, T.; Fliegl, H.; Kim, D.; et al. Nat. Commun. 2019, 10 (1), 3576.
9. [9]
  Peeks, M. D.; Jirasek, M.; Claridge, T. D. W.; Anderson, H. L.Angew. Chem. Int. Ed.2019, 58(44), 15717.
10. [10]
  Ni, Y.; Gopalakrishna, T. Y.; Phan, H.; Kim, T.; Herng, T. S.; Han, Y.; Tao, T.; Ding, J.; Kim, D.; Wu, J. Nat. Chem. 2020, 12 (3), 242.
11. [11]
  Rickhaus, M.; Jirasek, M.; Tejerina, L.; Gotfredsen, H.; Peeks, M. D.; Haver, R.; Jiang, H.-W.; Claridge, T. D. W.; Anderson, H. L. Nat. Chem. 2020, 12 (3), 236.
12. [12]
  Kikuchi, S. J. Chem. Educ. 1997, 74(2), 194.
13. [13]
  Heilbronner, E. Tetrahedron Lett. 1964, 29 (15), 1923.
14. [14]
15. [15]
  Herges, R. G. D. J. Phys. Chem.A 2001, 105 (23), 3214.
16. [16]
  Poater, J. J. Org. Chem.2004, 69 (22), 7537.
17. [17]
  Yoon, Z. S.; Osuka, A.; Kim, D. Nat. Chem. 2009, 1(2), 113.
18. [18]
  Aihara, J. J. Am. Chem. Soc. 1992, 114 (3), 865.
19. [19]
  Liu, C.; Ni, Y.; Lu, X.; Li, G.; Wu, J. G. Acc. Chem. Res.2019, 52 (8), 2309.
20. [20]
  Peeks, M. D.; Jirasek, M.; Claridge, T. D. W.; Anderson, H. L. Angew. Chem. Int. Ed. 2019, 10 (8), 2017.
21. [21]
  Nyulászi, L.; Schleyer, Pv. R. J. Am. Chem. Soc. 1999, 121, 6872.
22. [22]
  Chen, D.; Shen, T.; An, K.; Zhu, J.Commun. Chem.2018, 1, 18.
23. [23]
  Peeks, M. D.; Gong, J. Q.; McLoughlin, K.; Kobatake, T.; Haver, R.; Herz, L. M.; Anderson, H. L. J. Phys. Chem. Lett. 2019, 10 (8), 2017.
1. [1]
  Wentao Lin , Wenfeng Wang , Yaofeng Yuan , Chunfa Xu . Concerted Nucleophilic Aromatic Substitution Reactions. University Chemistry, 2024, 39(6): 226-230. doi: 10.3866/PKU.DXHX202310095
2. [2]
  Zitong Chen , Zipei Su , Jiangfeng Qian . Aromatic Alkali Metal Reagents: Structures, Properties and Applications. University Chemistry, 2024, 39(8): 149-162. doi: 10.3866/PKU.DXHX202311054
3. [3]
  Conghao Shi , Ranran Wang , Juli Jiang , Leyong Wang . The Illustration on Stereoisomers of Macrocycles Containing Multiple Chiral Centers via Tröger Base-based Macrocycles. University Chemistry, 2024, 39(7): 394-397. doi: 10.3866/PKU.DXHX202311034
4. [4]
  Lei Shi . Nucleophilicity and Electrophilicity of Radicals. University Chemistry, 2024, 39(11): 131-135. doi: 10.3866/PKU.DXHX202402018
5. [5]
  Dongheng WANG , Si LI , Shuangquan ZANG . Construction of chiral alkynyl silver chains and modulation of chiral optical properties. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 131-140. doi: 10.11862/CJIC.20240379
6. [6]
  Jin Tong , Shuyan Yu . Crystal Engineering for Supramolecular Chirality. University Chemistry, 2024, 39(3): 86-93. doi: 10.3866/PKU.DXHX202308113
7. [7]
  Peiran ZHAO , Yuqian LIU , Cheng HE , Chunying DUAN . A functionalized Eu³⁺ metal-organic framework for selective fluorescent detection of pyrene. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 713-724. doi: 10.11862/CJIC.20230355
8. [8]
  Xilin Zhao , Xingyu Tu , Zongxuan Li , Rui Dong , Bo Jiang , Zhiwei Miao . Research Progress in Enantioselective Synthesis of Axial Chiral Compounds. University Chemistry, 2024, 39(11): 158-173. doi: 10.12461/PKU.DXHX202403106
9. [9]
  Renxiao Liang , Zhe Zhong , Zhangling Jin , Lijuan Shi , Yixia Jia . A Palladium/Chiral Phosphoric Acid Relay Catalysis for the One-Pot Three-Step Synthesis of Chiral Tetrahydroquinoline. University Chemistry, 2024, 39(5): 209-217. doi: 10.3866/PKU.DXHX202311024
10. [10]
  Jun LUO , Baoshu LIU , Yunchang ZHANG , Bingkai WANG , Beibei GUO , Lan SHE , Tianheng CHEN . Europium(Ⅲ) metal-organic framework as a fluorescent probe for selectively and sensitively sensing Pb²⁺ in aqueous solution. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2438-2444. doi: 10.11862/CJIC.20240240
11. [11]
  Xin XIONG , Qian CHEN , Quan XIE . First principles study of the photoelectric properties and magnetism of La and Yb doped AlN. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1519-1527. doi: 10.11862/CJIC.20240064
12. [12]
  Haiying Wang , Andrew C.-H. Sue . How to Visually Identify Homochiral Crystals. University Chemistry, 2024, 39(3): 78-85. doi: 10.3866/PKU.DXHX202309004
13. [13]
  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
14. [14]
  Shihui Shi , Haoyu Li , Shaojie Han , Yifan Yao , Siqi Liu . Regioselectively Synthesis of Halogenated Arenes via Self-Assembly and Synergistic Catalysis Strategy. University Chemistry, 2024, 39(5): 336-344. doi: 10.3866/PKU.DXHX202312002
15. [15]
  Yuting Zhang , Zhiqian Wang . Methods and Case Studies for In-Depth Learning of the Aldol Reaction Based on Its Reversible Nature. University Chemistry, 2024, 39(7): 377-380. doi: 10.3866/PKU.DXHX202311037
16. [16]
  Keying Qu , Jie Li , Ziqiu Lai , Kai Chen . Unveiling the Mystery of Chirality from Tartaric Acid. University Chemistry, 2024, 39(9): 369-378. doi: 10.12461/PKU.DXHX202310091
17. [17]
  Yunhao Zhang , Yinuo Wang , Siran Wang , Dazhen Xu . Progress in Selective Construction of Functional Aromatics from Nitrogenous Cycloalkanes. University Chemistry, 2024, 39(11): 136-145. doi: 10.3866/PKU.DXHX202401083
18. [18]
  Jiakun BAI , Ting XU , Lu ZHANG , Jiang PENG , Yuqiang LI , Junhui JIA . A red-emitting fluorescent probe with a large Stokes shift for selective detection of hypochlorous acid. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1095-1104. doi: 10.11862/CJIC.20240002
19. [19]
  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
20. [20]
  Jin CHANG . Supercapacitor performance and first-principles calculation study of Co-doping Ni(OH)₂. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1697-1707. doi: 10.11862/CJIC.20240108

Get Citation

PDF

XML

Metrics

PDF Downloads(51)
Abstract views(1634)
HTML views(277)

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