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Chiral Recognition of Hexahelicene on a Surface via the Forming of Asymmetric Heterochiral Trimers

1
School of Physical Science and Technology, ShanghaiTech University, 393 Middle Huaxia Road, Pudong, Shanghai 201210, China
2
Shanghai Institute of Ceramics, Chinese Academy of Sciences, Shanghai 200050, China
3
University of Chinese Academy of Sciences, Beijing 100049, China
4
School of Chemistry and Chemical Engineering, State Key Lab of Metal Matrix Composites, Shanghai Jiao Tong University, Shanghai 200240, China
*
Authors to whom correspondence should be addressed.
Int. J. Mol. Sci. 2019, 20(8), 2018; https://doi.org/10.3390/ijms20082018
Received: 5 April 2019 / Revised: 20 April 2019 / Accepted: 21 April 2019 / Published: 24 April 2019
(This article belongs to the Section Physical Chemistry and Chemical Physics)
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Abstract

Chiral recognition among helical molecules is of essential importance in many chemical and biochemical processes. The complexity necessitates investigating manageable model systems for unveiling the fundamental principles of chiral recognition at the molecular level. Here, we reported chiral recognition in the self-assembly of enantiopure and racemic hexahelicene on a Au(111) surface. Combing scanning tunneling microscopy (STM) and atomic force microscopy (AFM) measurements, the asymmetric heterochiral trimers were observed as a new type of building block in racemic helicene self-assembly on Au(111). The intermolecular recognition of the heterochiral trimer was investigated upon manual separation so that the absolute configuration of each helicene molecule was unambiguously determined one by one, thus confirming that the trimer was “2+1” in handedness. These heterochiral trimers showed strong stability upon different coverages, which was also supported by theoretical calculations. Our results provide valuable insights for understanding the intermolecular recognition of helical molecules. View Full-Text
Keywords: chiral recognition; helicene; assembly; STM; nc-AFM chiral recognition; helicene; assembly; STM; nc-AFM
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Zhang, H.; Liu, H.; Shen, C.; Gan, F.; Su, X.; Qiu, H.; Yang, B.; Yu, P. Chiral Recognition of Hexahelicene on a Surface via the Forming of Asymmetric Heterochiral Trimers. Int. J. Mol. Sci. 2019, 20, 2018.

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