Citation: Zheng Dan, Yu Chengyuan, Zheng Lu, Zhan Yulin, Jiang Hua. Absolute control of helicity at the C-termini in quinoline oligoamide foldamers by chiral oxazolylaniline moieties[J]. Chinese Chemical Letters, ;2020, 31(3): 673-676. doi: 10.1016/j.cclet.2019.07.061 shu

Absolute control of helicity at the C-termini in quinoline oligoamide foldamers by chiral oxazolylaniline moieties

Department of Chemistry, Beijing Normal University, Beijing 100875, China

jiangh@bnu.edu.cn

Received Date: 6 July 2019
Revised Date: 21 July 2019
Accepted Date: 2 August 2019
Available Online: 2 August 2019

Figures(5)

Absolute one-handed chiral quinoline tetramers andoctamers containing different oxazolylanilines at the C-terminus have been synthesized. The absolute one-handed sense and diastereomeric excess values were valued by ¹H NMR. X-ray crystal diffractionand CD studies reveal that the S-oxazolylaniline always induces a P-handed helicity and the absolute helicity is driven by the stable three-center hydrogen bonding between protons in the amide and N atoms in oxazolylaniline and adjacent quinoline ring. CPL investigations demonstrated that S-CQ_n-a~d are CPL active and its g_lum values are dependent on its length. Interestingly, the sizes of the substituents in the chiral centers are different, however, they exert no effect on the dissymmetric factors g_abs and g_lum of quinoline oligoamide foldamers.
- Chiral induction,
- Helical chirality,
- Aromatic foldamer,
- Circularly polarized luminescence,
- Three-center hydrogen bonding
1. [1]
  L. Pauling, R.B. Corbey, H.R. Branson, Natl. Acad. Sci. U. S. A. 378 (1951) 205-211.
2. [2]
  J.D. Watson, F.H.C. Crick, Nature 171 (1953) 737-738. doi: 10.1038/171737a0
3. [3]
  (a) Z.T. Li, J.L. Hou, C. Li, H.P. Yi, Chem. -Asian J. 1 (2006) 766-778;
  (b) D.W. Zhang, X. Zhao, J.L. Hou, Z.T. Li, Chem. Rev. 112 (2012) 5271-5316.
4. [4]
  (a) H. Jiang, C. Dolain, J.M. Leger, et al., J. Am. Chem. Soc. 126 (2004) 1034-1035;
  (b) C. Dolain, H. Jiang, J.M. Leger, I. Huc, J. Am. Chem. Soc. 127 (2005) 12943-12951;
  (c) F.S. Bie, Y. Wang, J. Shang, et al., Eur. J. Org. Chem. 8 (2013) 8135-8144;
  (d) H. Jiang, Q.L. Li, G.X. Wang, Chin. J. Org. Chem. 38 (2018) 1065-1084.
5. [5]
  C. Li, G.T. Wang, H.P. Yi, et al., Org. Lett. 9 (2007) 1797-1800. doi: 10.1021/ol070492l
6. [6]
  (a) A.M. Kendhale, L. Poniman, Z.Y. Dong, et al., J. Org. Chem. 76 (2011) 195-200;
  (b) Y. Ferrand, A.M. Kendhale, B. Kauffmann, et al., J. Am. Chem. Soc. 132 (2010) 7858-7859;
  (c) L. Zheng, Y.L. Zhan, C.Y. Yu, et al., Org. Lett. 19 (2017) 1482-1485;
  (d) H.Y. Hu, J.F. Xiang, Y. Yang, C.F. Chen, Org. Lett. 10 (2008) 1275-1278.
7. [7]
  I. Huc, H. Jiang, Organic foldamers and helices, in: J.W. Steed, P.A. Gale (Eds.), Supramolecular Chemistry: From Molecules to Nanomaterials, John Wiley & Sons Ltd, Chichester, 2012, pp. 2183-2206.
8. [8]
  (a) N. Tamaoki, M. Wada, J. Am. Chem. Soc. 128 (2006) 6284-6285;
  (b) L.B. Wang, L. Yin, W. Zhang, et al., J. Am. Chem. Soc. 139 (2017) 13218-13226;
  (c) G. Yang, L. Zhu, J. Hu, et al., Chem. -Eur. J. 23 (2017) 8032-8038;
  (d) Y. Lu, L.L. Zhu, Chin. Chem. Lett. 29 (2018) 1591-1600.
9. [9]
  (a) C.S. Wang, H.S. Fei, Y. Qiu, et al., Appl. Phys. Lett. 74 (1999) 18-21;
  (b) A. Natansohn, P. Rochon, Chem. Rev. 102 (2002) 4139-4175;
  (c) D. Sankar, P.K. Palanisamy, S. Manickasundaram, P. Kannan, Opt. Mater. (Amst) 28 (2005) 1101-1107.
10. [10]
  J. Jimenez, L. Cerdan, F. Moreno, et al., J. Phys. Chem. C 121 (2017) 5287-5292. doi: 10.1021/acs.jpcc.7b00654
11. [11]
  L. Zheng, C.Y. Yu, Y.L. Zhan, et al., Chem. -Eur. J. 23 (2017) 5361-5367. doi: 10.1002/chem.201700134
12. [12]
  D. Zheng, L. Zheng, C.Y. Yu, et al., Org. Lett. 21 (2019) 2555-2559. doi: 10.1021/acs.orglett.9b00450
13. [13]
  M. Luo, Curr. Org. Synth. 12 (2015) 660-672. doi: 10.2174/157017941205150821153905
14. [14]
  H. Jiang, J.M. Leger, C. Dolain, et al., Tetrahedron 59 (2003) 8365-8374. doi: 10.1016/j.tet.2003.08.058
15. [15]
  (a) J.P. Riehl, F.S. Richardson, Chem. Rev. 86 (1986) 1-16;
  (b) H. Anetai, T. Takeda, N. Hoshino, et al., J. Phys. Chem. C 122 (2018) 6323-6331.
16. [16]
  (a) E.M. Sanchez-Carnerero, A.R. Agarrabeitia, F. Moreno, et al., Chem. -Eur. J. 21 (2015) 13488-13500;
  (b) H. Maeda, Y. Bando, K. Shimomura, et al., J. Am. Chem. Soc. 133 (2011) 9266-9269;
  (c) C.M. Cruz, S. Castro Fernandez, E. Macoas, et al., Angew. Chem. Int. Ed. 57 (2018) 14782-14786.
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