Homochiral Recognition among Organic Molecules on Copper(110)
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† Institute of Physics, Chinese Academy of Sciences, Beijing 100190, China
‡ Key Lab of Supramolecular Structure and Materials, Jilin University, Changchun 130023, China
§ Empa, Swiss Federal Laboratories for Materials Testing and Research, Überlandstrasse 129, CH-8600 Dübendorf, Switzerland
*To whom correspondence should be addressed. E-mail: [email protected] or [email protected].
Abstract
The adsorption of a prochiral quinacridone derivative (QA16C) with two alkyl chains of 16 carbon atoms on a Cu(110) surface was investigated with variable-temperature scanning tunneling microscopy. QA16C molecules prefer to assemble at 150 K into short homochiral molecular lines with two enantiomorphous orientations in which the lateral alkyl chains exhibit partial disorder. With increasing sample temperatures, the QA16C lines form larger well-ordered homochiral domains. As a reason for the homochiral recognition, we identify a rigid alignment of the molecule due to the interaction with the substrate. In addition, lateral intermolecular interactions in the form of hydrogen bonding and van der Waals interactions are identified.
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- Arántzazu González-Campo, David B. Amabilino. Biomolecules at Interfaces: Chiral, Naturally. 2013,,, 109-156. DOI: 10.1007/128_2012_405.
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- Karl-Heinz Ernst. Molecular chirality at surfaces. physica status solidi (b) 2012, 249 (11) , 2057-2088. DOI: 10.1002/pssb.201248188.
- Erin V. Iski, Heather L. Tierney, April D. Jewell, E. Charles H. Sykes. Spontaneous Transmission of Chirality through Multiple Length Scales. Chemistry – A European Journal 2011, 17 (26) , 7205-7212. DOI: 10.1002/chem.201100268.