Citation: Guiyang Xia, Lingyan Wang, Huan Xia, Yuzhuo Wu, Yanan Wang, Haiyu Hu, Sheng Lin. Circularly polarized luminescence of talarolactones (+)/(−)-A and (+)/(−)-C: The application of CPL-calculation in stereochemical assignment[J]. Chinese Chemical Letters, ;2022, 33(9): 4253-4256. doi: 10.1016/j.cclet.2022.03.032 shu

Circularly polarized luminescence of talarolactones (+)/(−)-A and (+)/(−)-C: The application of CPL-calculation in stereochemical assignment

Guiyang Xia ^a ,
Lingyan Wang ^a ,
Huan Xia ^a ,
Yuzhuo Wu ^a ,
Yanan Wang ^b ,
Haiyu Hu ^{b, *,} ,
Sheng Lin ^{a, c, **,}

a.
Key Laboratory of Chinese Internal Medicine of Ministry of Education and Beijing, Dongzhimen Hospital, Beijing University of Chinese Medicine, Beijing 100700, China
b.
State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China
c.
Key Laboratory for Qinghai-Tibet Plateau Phytochemistry of Qinghai Province, College of Pharmaceutical, Qinghai Nationalities University, Xining 810007, China

haiyu.hu@imm.ac.cn

lsznn@bucm.edu.cn

Received Date: 5 February 2022
Revised Date: 8 March 2022
Accepted Date: 8 March 2022
Available Online: 11 March 2022

Figures(6)

Two pairs of fluorescent natural products, talarolactones (+)/(−)-A and (+)/(−)-C [(+)/(−)-1 and (+)/(−)-2], were discovered and characterized as a new family of circularly polarized luminescence-active small organic molecules (CPL-SOMs) with high fluorescence efficiency and fascinating CPL properties. The CPL (|g_lum|) levels of enantiomerically pure (+)/(−)-1 and (+)/(−)-2 in solution falls into the usual range (10⁻⁵−10⁻³) considering their pure organic nature, but the sign of CPL were found to be closely related to the absolute configuration of C-8. The high agreement of the measured CPL spectra of (+)/(−)-1 and (+)/(−)-2 with the time-dependent density functional theory (TDDFT) calculated ones demonstrated the usefulness of CPL-calculation as a unique method for stereochemical assignment. This study may open up a new perspective for the stereochemical studies and the future development of CPL materials.
- Circularly polarized luminescence,
- Natural products,
- Stereochemical assignment,
- Talarolactones (+)/(−)-A,
- Talarolactones (+)/(−)-C
1. [1]
  I.M. Daly, M.J. How, J.C. Partridge, et al., Nat. Commun. 7 (2016) 12140. doi: 10.1038/ncomms12140
2. [2]
  J. Bailey, Science 281 (1998) 672-674. doi: 10.1126/science.281.5377.672
3. [3]
  H. Wynberg, E.W. Meijer, J.C. Hummelen, et al., Nature 286 (1980) 641-642. doi: 10.1038/286641a0
4. [4]
  J.L. Ma, Q. Peng, C.H. Zhao, Chem. Eur. J. 25 (2019) 15441-15454. doi: 10.1002/chem.201903252
5. [5]
  M. Li, M.Y. Wang, Y.F. Wang, et al., Angew. Chem. Int. Ed. 60 (2021) 20728-20733. doi: 10.1002/anie.202108011
6. [6]
  C. Wang, T. Jiang, X. Ma, Chin. Chem. Lett. 31 (2020) 2921-2924. doi: 10.1016/j.cclet.2020.03.021
7. [7]
  S. Jiang, S. Zhou, Y. Chen, et al., Chin. Chem. Lett. 33 (2022) 2442–2446. doi: 10.1016/j.cclet.2021.10.050
8. [8]
  J. Zhang, L. Dai, A.M. Webster, et al., Angew. Chem. Int. Ed. 60 (2021) 1004-1010. doi: 10.1002/anie.202012133
9. [9]
  R. Carr, N.H. Evans, D. Parker, Chem. Soc. Rev. 41 (2012) 7673-7686. doi: 10.1039/c2cs35242g
10. [10]
  J. Han, D. Yang, X. Jin, et al., Angew. Chem. Int. Ed. 58 (2019) 7013-7019. doi: 10.1002/anie.201902090
11. [11]
  C.H. Chen, W.H. Zheng, Org. Lett. 23 (2021) 5554-5558. doi: 10.1021/acs.orglett.1c01924
12. [12]
  H.W. Li, M. Li, Z.H. Zhao, et al., Org. Lett. 23 (2021) 4759-4763. doi: 10.1021/acs.orglett.1c01485
13. [13]
  F. Zhou, Z. Huang, Z. Huang, et al., Org. Lett. 23 (2021) 4559-4563. doi: 10.1021/acs.orglett.1c01212
14. [14]
  W. -B. Lin, M. Li, L. Fang, et al., Chin. Chem. Lett. 29 (2018) 40-46. doi: 10.1117/12.2289207
15. [15]
  O. Oki, C. Kulkarni, H. Yamagishi, et al., J. Am. Chem. Soc. 143 (2021) 8772-8779. doi: 10.1021/jacs.1c03185
16. [16]
  L. Wang, L. Yin, W. Zhang, et al., J. Am. Chem. Soc. 139 (2017) 13218-13226. doi: 10.1021/jacs.7b07626
17. [17]
  R. Duval, C. Duplais, Nat. Prod. Rep. 34 (2017) 161-193. doi: 10.1039/C6NP00111D
18. [18]
  H. Tanaka, Y. Inoue, T. Mori, ChemPhotoChem 2 (2018) 386-402. doi: 10.1002/cptc.201800015
19. [19]
  C.A. Emeis, L.J. Oosterhoff, Chem. Phys. Lett. 1 (1967) 129-132. doi: 10.1016/0009-2614(67)85007-3
20. [20]
  H.P.J.M. Dekkers, L.E. Closs, J. Am. Chem. Soc. 98 (2002) 2210-2219.
21. [21]
  C.K. Luk, F.S. Richardson, J. Am. Chem. Soc. 96 (2002) 2006-2009.
22. [22]
  K. Dhbaibi, L. Favereau, M. Srebro-Hooper, et al., Chem. Sci. 9 (2018) 735-742. doi: 10.1039/C7SC04312K
23. [23]
  K. Takaishi, K. Iwachido, R. Takehana, et al., J. Am. Chem. Soc. 141 (2019) 6185-6190. doi: 10.1021/jacs.9b02582
24. [24]
  H. Tanaka, M. Ikenosako, Y. Kato, et al., Commun. Chem. 1 (2018) 38. doi: 10.1038/s42004-018-0035-x
25. [25]
  G. Longhi, E. Castiglioni, S. Abbate, et al., Chirality 25 (2013) 589-599. doi: 10.1002/chir.22176
26. [26]
  B. Pritchard, J. Autschbach, ChemPhysChem 11 (2010) 2409-2415. doi: 10.1002/cphc.201000054
27. [27]
  A. Mandi, T. Kurtan, Nat. Prod. Rep. 36 (2019) 889-918. doi: 10.1039/c9np00002j
28. [28]
  Y.Z. Wu, G.Y. Xia, H. Xia, et al., J. Nat. Prod. 85 (2022) 248-255. doi: 10.1021/acs.jnatprod.1c01025
29. [29]
  G.Y. Xia, L.Y. Wang, J.F. Zhang, et al., Chin. J. Nat. Med. 18 (2020) 75-80.
30. [30]
  Y.Z. Wu, H.W. Zhang, Z.H. Sun, et al., Eur. J. Med. Chem. 145 (2018) 717-725. doi: 10.1016/j.ejmech.2018.01.030
31. [31]
  Y.N. Wang, G.Y. Xia, L.Y. Wang, et al., Org. Lett. 20 (2018) 7341-7344. doi: 10.1021/acs.orglett.8b03323
32. [32]
  W.H. Yuan, M.T. Teng, Y.F. Yun, et al., J. Nat. Prod. 83 (2020) 1716-1720. doi: 10.1021/acs.jnatprod.0c00024
33. [33]
  K. Takase, K. Noguchi, K. Nakano, Org. Lett. 19 (2017) 5082-5085. doi: 10.1021/acs.orglett.7b02337
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2. [2]
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  Shehla Khalid , Muhammad Bilal , Nasir Rasool , Muhammad Imran . Photochemical reactions as synthetic tool for pharmaceutical industries. Chinese Chemical Letters, 2024, 35(9): 109498-. doi: 10.1016/j.cclet.2024.109498
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  Wenying Cui , Zhetong Jin , Wentao Fu , Chengshuo Shen . Flag-hinge-like highly luminescent chiral nanographenes with twist geometry. Chinese Chemical Letters, 2024, 35(11): 109667-. doi: 10.1016/j.cclet.2024.109667
11. [11]
  Fengying Ye , Ming Hu , Jun Luo , Wei Yu , Zhirong Xu , Jinjin Fu , Yansong Zheng . Significantly boosting circularly polarized luminescence by synergy of helical and planar chirality. Chinese Chemical Letters, 2025, 36(5): 110724-. doi: 10.1016/j.cclet.2024.110724
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  Sifan Du , Yuan Wang , Fulin Wang , Tianyu Wang , Li Zhang , Minghua Liu . Evolution of hollow nanosphere to microtube in the self-assembly of chiral dansyl derivatives and inversed circularly polarized luminescence. Chinese Chemical Letters, 2024, 35(7): 109256-. doi: 10.1016/j.cclet.2023.109256
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  Tao Yang , Kaijiao Duan , Siyu Li , Jing Wei , Qingdi Yang , Qian Wang . A Comprehensive and Innovative Chemical Experimental Teaching: Extraction and Identification of Tea Polyphenols from Pu'er Tea and the Application in Hand Cream Making. University Chemistry, 2024, 39(8): 270-275. doi: 10.3866/PKU.DXHX202312040
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