Citation: Yunying Xu, Aiyou Hao, Pengyao Xing. Distorted aryl homochirality controlled by β-sheet folding[J]. Chinese Chemical Letters, ;2023, 34(11): 108492. doi: 10.1016/j.cclet.2023.108492 shu

Distorted aryl homochirality controlled by β-sheet folding

School of Chemistry and Chemical Engineering, Shandong University, Ji'nan 250100, China

haoay@sdu.edu.cn

xingpengyao@sdu.edu.cn

Received Date: 5 January 2023
Revised Date: 7 April 2023
Accepted Date: 20 April 2023
Available Online: 23 April 2023

Figures(6)

Distortion of planar aromatics occurs in the fused rings conjugated with bulky substituents, which generates racemic enantiomers with high transformation energy barriers. However, direct synthesis of homochiral distorted aryl compounds is a very challenging task. Here, we presented a molecular folding strategy to control distorted aryl homochirality. Amino acids and their derivatives conjugated on the polycyclic aromatic hydrocarbons including benzenes, naphthalenes and triphenylenes, which formed parallel β-sheet arrays through intramolecular hydrogen bonds. The folding behavior enabled distorted or twisted geometry of aromatics, of which the handedness was associated with the absolute chirality of amino acids. X-ray crystallography, theoretical calculations and circular dichroism spectroscopy verified the distorted homochirality in the solid and solution phase. The relatively small rotational barrier between the enantiomers made the molecule sensitive to the environment and thus realized the solvent-controlled chiral inversion. The β-sheet folding strategy can be widely used in polycyclic aromatic hydrocarbons with various functions, which provided a promising strategy to control inherent chirality of aromatics with adaptive chiroptical responses.
- Distorted chirality,
- Folding,
- Solvent strategy,
- Chiroptical activity
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