Citation: Hui Zhang, Aihua Qi, Dan Li, Rongxing Li. 光学活性和手性光谱的溯源和发展[J]. University Chemistry, ;2022, 37(1): 210500. doi: 10.3866/PKU.DXHX202105009 shu

光学活性和手性光谱的溯源和发展

Hui Zhang ^1,, ,
Aihua Qi ² ,
Dan Li ¹ ,
Rongxing Li ²

1.
College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, Fujian Province, China;
2.
Dalian Huayang Analytical Instruments Co., Ltd., Dalian 116001, Liaoning Province, China

Corresponding author: Hui Zhang, huizhang@xmu.edu.cn
Received Date: 6 May 2021

概述了19世纪以来光学活性和手性光谱的发现和发展，着重对旋光色散（ORD）、电子圆二色（ECD）和振动圆二色（VCD）光谱的发展背景和基本原理作出介绍。其中特别提及华人科学家徐光宪和徐云洁在手性光谱发展历程中的杰出贡献。
1. [1]
  Berova, N.; Polavarapu, P. L.; Nakanishi, K.; Woody, R. W. Comprehensive Chiroptical Spectroscopy, John Wiley & Sons, Ltd.:Chichester, UK, 2012.
2. [2]
3. [3]
  Laur, P. A. Historical Overview. In Comprehensive Chiroptical Spectroscopy; Berova, N.; Polavarapu, P. L.; Nakanishi, K.; Woody, R. W. Eds.; John Wiley & Sons, Ltd.:Chichester, UK, 2012; pp. 3-35.
4. [4]
  Mason, S. F. Molecular Optical Activity and Chiral Discriminations. Cambridge University Press:Cambridge, UK, 1982.
5. [5]
  Nafie, L. A. Vibrational Optical Activity:Principles and Applications. John Wiley & Sons, Ltd.:Chichester, UK, 2011; pp. 1-34.
6. [6]
  Barron, L. D. Molecular Light Scattering and Optical Activity, 2nd ed.; Cambridge University Press:Cambridge, UK, 2004.
7. [7]
  Crabbé, P. Optical Rotatory Dispersion and Circular Dichroism in Organic Chemistry. Holden-Day, Inc.:San Francisco, CA, USA, 1965.
8. [8]
9. [9]
  Pasteur, L. Ann. Chim. Phys. 1850, 28 (3), 56.
10. [10]
  Tobe, Y. Mendeleev Commun. 2003, 13 (3), 93.
11. [11]
  Ramsay, O. B. Stereochemistry. Heyden & Son Ltd.:London, UK, 1981.
12. [12]
  Arndtsen, A. Ann. Phys. 1858, 181 (10), 312.
13. [13]
  Landolt, H. Liebigs Ann. Chem. 1877, 189 (3), 241.
14. [14]
  Landolt, H. Das Optische Drehungsvermögen Organischer Substanzen und die Praktischen Anwendungen Desselben. Vieweg und Sohn:Braunschweig, Germany, 1879.
15. [15]
  Haidinger, W. Ann. Phys. 1847, 146 (4), 531.
16. [16]
  Dove, H. W. Ann. Phys. 1860, 186 (6), 279.
17. [17]
  Perucca, E. Ann. Phys. 1914, 350 (19), 463.
18. [18]
  Perucca, E. Nuovo Cimento 1919, 18 (1), 112.
19. [19]
  Burkov, V. I.; Egorysheva, A. V.; Kargin, Y. F.; Mar'in A A.; Fedotov, E. V. Crystallogr. Rep. 2005, 50 (3), 461.
20. [20]
  King, N. Amethyst.[2021-03-20]. https://www.mindat.org/min-198.html
21. [21]
  Bolano, A. Amethyst:Characteristics and Properties.[2018-08-17]. https://sciencetrends.com/amethyst-characteristics-and-properties/
22. [22]
  Cotton, A. C. R. Hebd. Seances Acad. Sci. (Paris). 1895, 120, 989.
23. [23]
  Cotton, A. C. R. Hebd. Seances Acad. Sci. (Paris). 1895, 120, 1044.
24. [24]
  Cotton, A. J. Phys. Théor. Appl. 1896, 5 (1), 237.
25. [25]
  Lifschitz, J. Rec. Trav. Chim. Pays-Bas 1922, 41, 627.
26. [26]
  Kahr, B.; Bing, Y.; Kaminsky, W.; Viterbo, D. Angew. Chem. Int. Ed. 2009, 48 (21), 3744.
27. [27]
  Bing, Y.; Selassi, D.; Paradise, R. H.; Christine, I.; Kramer, N.; Sadilek, M.; Kaminsky, W.; Kahr, B. J. Am. Chem. Soc. 2010, 132 (21), 7454.
28. [28]
  Rosenfeld, L. Z. Phys. 1929, 52 (3-4), 161.
29. [29]
  Kuhn, W. Z. Phys. Chem. 1936, B31 (1), 23.
30. [30]
  Tschugaeff, L. Trans. Faraday Soc. 1914, 10 (8), 70.
31. [31]
  Nyholm, R. S. Phys. Eng. Sci. 1967, 297 (1448), 2.
32. [32]
  Ingold, C. Proc. Roy. Soc. A 1967, 297 (1448), 171.
33. [33]
  Polavarapu, P. L. Chirality 2002, 14 (10), 768.
34. [34]
  McCaffery, A. J.; Mason, S. F. Mol. Phys. 1963, 6 (4), 359.
35. [35]
  Mason, S. F. Proc. Roy. Soc. A 1967, 297 (1448), 3.
36. [36]
  Beckmann, C. O.; Cohen, K. J. Chem. Phys. 1936, 4 (12), 784.
37. [37]
  Charney, E. The Molecular Basis of Optical Activity, Optical Rotatory Dispersion and Circular Dichroism. John Wiley & Sons:New York, NY, USA, 1979.
38. [38]
39. [39]
40. [40]
41. [41]
42. [42]
43. [43]
44. [44]
  Nafie, L. A. Infrared vibrational optical activity:measurement and instrumentation. In Comprehensive Chiroptical Spectroscopy; Berova, N., Polavarapu, P. L., Nakanishi, K., Woody, R. W., Eds.; John Wiley & Sons, Ltd.:Chichester, UK, 2012; pp. 115-146.
45. [45]
46. [46]
  Bijvoet, J. M.; Peerdeman, A. F.; van Bommel, A. J. Nature 1951, 168 (4268), 271.
47. [47]
  Mitchell, S. The Cotton Effect and Related Phenomena. G. Bell & Sons, Ltd.:London, UK, 1933.
48. [48]
  Kuhn, W.; Szabo, A. Z. Phys. Chem. 1932, B15, 59.
49. [49]
  Mason, S. F. Quart. Rev. 1963, 17 (1), 206.
50. [50]
51. [51]
  Taniguchi, T.; Monde, K. J. Am. Chem. Soc. 2012, 134 (8), 3695.
52. [52]
  Taniguchi, T.; Manai, D.; Shibata, M.; Itabashi, Y.; Monde, K. J. Am. Chem. Soc. 2015, 137 (38), 12191.
53. [53]
  Covington, C. L.; Nicu, V. P.; Polavarapu, P. L. J. Phys. Chem. A 2015, 119 (42), 10589.
54. [54]
55. [55]
  Nafie, L. A. Vibrational Optical Activity:Principles and Applications. John Wiley & Sons, Ltd.:Chichester, UK, 2011; pp. 1-34.
56. [56]
  Sadlej, J. S.; Dobrowolski, J. C.; Rode, J. E. Chem. Soc. Rev. 2010, 39 (5), 1478.
57. [57]
  Kuhn, W. Trans. Faraday Soc. 1930, 26, 293.
58. [58]
  Holzwarth, G.; Chabay, I. J. Chem. Phys. 1972, 57 (4), 1632.
59. [59]
  Schellman, J. A. J. Chem. Phys. 1973, 58 (7), 2882.
60. [60]
  Holzwarth, G.; Hsu, E. C.; Mosher, H. S.; Faulkner, T. R.; Moscowitz, A. J. Am. Chem. Soc. 1974, 96 (1), 251.
61. [61]
  Stephens, P. J.; Devlin, F. J.; Pan, J.-J. Chirality 2008, 20 (5), 243.
62. [62]
  Nafie, L. A.; Cheng, J. C.; Stephens, P. J. J. Am. Chem. Soc. 1975, 97 (13), 3842.
63. [63]
  Nafie, L. A.; Keiderling, T. A.; Stephens, P. J. J. Am. Chem. Soc. 1976, 98 (10), 2715.
64. [64]
  Devlin, F. J.; Stephens, P. J.; Besse, P. Tetrahedron:Asymmetry 2005, 16 (8), 1557.
65. [65]
  Buckingham, A. D.; Fowler, P. W.; Galwas, P. A. Chem. Phys. 1987, 112 (1), 1.
66. [66]
  Stephens, P. J. J. Phys. Chem. 2002, 89 (5), 748.
67. [67]
  Cheeseman, J. R.; Frisch, M. J.; Devlin, F. J.; Stephens, P. J. Chem. Phys. Lett. 1996, 252 (2), 211.
68. [68]
  Yang, G.; Xu, Y.; Hou, J.-B.; Zhang, H.; Zhao, Y.-F. Chem. Eur. J. 2010, 16 (8), 2518.
69. [69]
  Yang, G.; Xu, Y.; Hou, J.-B.; Zhang, H.; Zhao, Y.-F. Dalton Trans. 2010, 39 (30), 6953.
70. [70]
  Zhang, Y.; Poopari, M. R.; Cai, X.; Savin, A.; Dezhahang, Z.; Cheramy, J.; Xu, Y. J. Nat. Prod. 2016, 79 (4), 1012.
71. [71]
  Bader, R. F. W. Acc. Chem. Res. 1985, 18 (1), 9.
72. [72]
  Losada, M.; Nguyen, P.; Xu, Y. J. Phys. Chem. A 2008, 112 (25), 5621.
73. [73]
  Thomas, J.; Sukhorukov, O.; Jäger, W.; Xu, Y. Angew. Chem. Int. Ed. 2014, 53 (4), 1156.
74. [74]
  Perera, A. S.; Thomas, J.; Poopari, M. R.; Xu, Y. Front. Chem. 2016, 4, 1.
75. [75]
  Merten, C.; Xu, Y. Angew. Chem. Int. Ed. 2013, 52 (7), 2073.
1. [1]
  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
2. [2]
  Wenkai Chen , Yunjia Shen , Xiangmeng Kong , Yanli Zeng . Quantum Chemistry Calculation of Key Physical Quantity in Circularly Polarized Luminescence: Introducing an Exploratory Computational Chemistry Experiment. University Chemistry, 2025, 40(3): 83-91. doi: 10.12461/PKU.DXHX202405018
3. [3]
  Yonghui ZHOU , Rujun HUANG , Dongchao YAO , Aiwei ZHANG , Yuhang SUN , Zhujun CHEN , Baisong ZHU , Youxuan ZHENG . Synthesis and photoelectric properties of fluorescence materials with electron donor-acceptor structures based on quinoxaline and pyridinopyrazine, carbazole, and diphenylamine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 701-712. doi: 10.11862/CJIC.20230373
4. [4]
  Cuicui Yang , Bo Shang , Xiaohua Chen , Weiquan Tian . Understanding the Wave-Particle Duality and Quantization of Confined Particles Starting from Classic Mechanics. University Chemistry, 2025, 40(3): 408-414. doi: 10.12461/PKU.DXHX202407066
5. [5]
  Xian BI , Sisi WANG , Jinyue ZHANG , Yujia PENG , Zhen SHEN , Hua LU . Discovery, development, and perspectives of circularly polarized luminescent materials based on β-isoindigo skeletons. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1049-1057. doi: 10.11862/CJIC.20240456
6. [6]
  Liang TANG , Jingfei NI , Kang XIAO , Xiangmei LIU . Synthesis and X-ray imaging application of lanthanide-organic complex-based scintillators. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1892-1902. doi: 10.11862/CJIC.20240139
7. [7]
  Jin Tong , Shuyan Yu . Crystal Engineering for Supramolecular Chirality. University Chemistry, 2024, 39(3): 86-93. doi: 10.3866/PKU.DXHX202308113
8. [8]
  Qiuting Zhang , Fan Wu , Jin Liu , Zian Lin . Chromatographic Stationary Phase and Chiral Separation Using Frame Materials. University Chemistry, 2025, 40(4): 291-298. doi: 10.12461/PKU.DXHX202405174
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]
  Yinuo Wang , Siran Wang , Yilong Zhao , Dazhen Xu . Selective Synthesis of Diarylmethyl Anilines and Triarylmethanes via Multicomponent Reactions: Introduce a Comprehensive Experiment of Organic Chemistry. University Chemistry, 2024, 39(8): 324-330. doi: 10.3866/PKU.DXHX202401063
11. [11]
  Haiying Wang , Andrew C.-H. Sue . How to Visually Identify Homochiral Crystals. University Chemistry, 2024, 39(3): 78-85. doi: 10.3866/PKU.DXHX202309004
12. [12]
  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
13. [13]
  Zihao Guo , Shichen Ma , Kin Shing Chan . 烯烃环化反应中6电子试剂的等瓣相似性和等电子关系. University Chemistry, 2025, 40(6): 160-166. doi: 10.12461/PKU.DXHX202408038
14. [14]
  Jingjing QING , Fan HE , Zhihui LIU , Shuaipeng HOU , Ya LIU , Yifan JIANG , Mengting TAN , Lifang HE , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two complexes of dimethylglyoxime organotin. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1301-1308. doi: 10.11862/CJIC.20240003
15. [15]
  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
16. [16]
  Qi Wang , Yicong Gao , Feng Lu , Quli Fan . Preparation and Performance Characterization of the Second Near-Infrared Phototheranostic Probe: A New Design and Teaching Practice of Polymer Chemistry Comprehensive Experiment. University Chemistry, 2024, 39(11): 342-349. doi: 10.12461/PKU.DXHX202404141
17. [17]
  Ke QIAO , Yanlin LI , Shengli HUANG , Guoyu YANG . Advancements in asymmetric catalysis employing chiral iridium (ruthenium) complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2091-2104. doi: 10.11862/CJIC.20240265
18. [18]
  Ruiying WANG , Hui WANG , Fenglan CHAI , Zhinan ZUO , Benlai WU . Three-dimensional homochiral Eu(Ⅲ) coordination polymer and its amino acid configuration recognition. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 877-884. doi: 10.11862/CJIC.20250052
19. [19]
  Shuhui Li , Rongxiuyuan Huang , Yingming Pan . Electrochemical Synthesis of 2,5-Diphenyl-1,3,4-Oxadiazole: A Recommended Comprehensive Organic Chemistry Experiment. University Chemistry, 2025, 40(5): 357-365. doi: 10.12461/PKU.DXHX202407028
20. [20]
  Linjie ZHU , Xufeng LIU . Synthesis, characterization and electrocatalytic hydrogen evolution of two di-iron complexes containing a phosphine ligand with a pendant amine. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 939-947. doi: 10.11862/CJIC.20240416

Get Citation

PDF

XML

Metrics

PDF Downloads(24)
Abstract views(1172)
HTML views(175)

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