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
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