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Direct Observation of Enantiospecific Substitution in a Two-Dimensional Chiral Phase Transition

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Beijing National Laboratory of Condensed Matter Physics, Institute of Physics, Chinese Academy of Sciences, Beijing 100190, China, Key Lab of Supramolecular Structure and Materials, Jilin University, Changchun 130023, China, and Empa, Swiss Federal Laboratories for Materials Testing and Research, Überlandstrasse 129, CH-8600 Dübendorf, Switzerland
†Chinese Academy of Sciences.
‡Jilin University.
§Swiss Federal Laboratories for Materials Testing and Research.
Cite this: J. Am. Chem. Soc. 2010, 132, 30, 10440-10444
Publication Date (Web):July 13, 2010
https://doi.org/10.1021/ja102989y
Copyright © 2010 American Chemical Society
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Abstract

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Initial stages of a chiral phase transition in the monolayer of a quinacridone derivative on the Au(111) surface were investigated by scanning tunneling microscopy at submolecular resolution. The prochiral molecules form a homochiral lamella phase at low coverages upon adsorption. A transition to a racemate lattice is observed with increasing coverage. Enantiomers of a homochiral lamella line become specifically substituted by opposite enantiomers such that a heterochiral structure evolves. Due to the higher density, lateral alkyl chains are bent away from the surface. Our findings are significant for the understanding and control of chiral phase transitions in related molecular systems like liquid crystals.

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STM images of mirror and rotational domain boundaries, structure model for the lamella phase, long-range STM images of all phases, unit cell parameters of the homochiral and racemic structures, STM images after annealing, as well as ab initio and MM+ calculation details. This material is available free of charge via the Internet at http://pubs.acs.org.

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Cited By

This article is cited by 29 publications.

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  2. Hai Cao, Kazukuni Tahara, Shintaro Itano, Yoshito Tobe, and Steven De Feyter . Odd–Even Effects in Chiral Phase Transition at the Liquid/Solid Interface. The Journal of Physical Chemistry C 2017, 121 (19) , 10430-10438. DOI: 10.1021/acs.jpcc.7b02262.
  3. Anaïs Mairena, Laura Zoppi, Johannes Seibel, Alix F. Tröster, Konstantin Grenader, Manfred Parschau, Andreas Terfort, and Karl-Heinz Ernst . Heterochiral to Homochiral Transition in Pentahelicene 2D Crystallization Induced by Second-Layer Nucleation. ACS Nano 2017, 11 (1) , 865-871. DOI: 10.1021/acsnano.6b07424.
  4. Shu-Ying Li, Ting Chen, Lin Wang, Bing Sun, Dong Wang, and Li-Jun Wan . Enantiomeric Excess-Tuned 2D Structural Transition: From Heterochiral to Homochiral Supramolecular Assemblies. Langmuir 2016, 32 (27) , 6830-6835. DOI: 10.1021/acs.langmuir.6b01418.
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  6. Mihaela Enache, Laura Maggini, Anna Llanes-Pallas, Thomas A. Jung, Davide Bonifazi, and Meike Stöhr . Coverage-Dependent Disorder-to-Order Phase Transformation of a Uracil Derivative on Ag(111). The Journal of Physical Chemistry C 2014, 118 (28) , 15286-15291. DOI: 10.1021/jp503188m.
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  10. Hui Lu, E. Wenlong, Zhibo Ma, Xueming Yang. Organometallic polymers synthesized from prochiral molecules by a surface-assisted synthesis on Ag(111). Physical Chemistry Chemical Physics 2020, 22 (15) , 8141-8145. DOI: 10.1039/C9CP06893G.
  11. Wei-Qi Yu, Hong-Jun Xiao, Ge-Ming Wang. Interface properties and electronic structures of aromatic molecules with anhydride and thio-functional groups on Ag (111) and Au (111) substrates. Chinese Physics B 2019, 28 (10) , 103101. DOI: 10.1088/1674-1056/ab4276.
  12. Juyeon Park, Ju‐Hyung Kim, Sunmi Bak, Kazukuni Tahara, Jaehoon Jung, Maki Kawai, Yoshito Tobe, Yousoo Kim. On‐Surface Evolution of meso ‐Isomerism in Two‐Dimensional Supramolecular Assemblies. Angewandte Chemie 2019, 131 (28) , 9713-9720. DOI: 10.1002/ange.201904290.
  13. Juyeon Park, Ju‐Hyung Kim, Sunmi Bak, Kazukuni Tahara, Jaehoon Jung, Maki Kawai, Yoshito Tobe, Yousoo Kim. On‐Surface Evolution of meso ‐Isomerism in Two‐Dimensional Supramolecular Assemblies. Angewandte Chemie International Edition 2019, 58 (28) , 9611-9618. DOI: 10.1002/anie.201904290.
  14. . Asymmetric Adsorption on Achiral Substrates. 2018,,, 93-163. DOI: 10.1002/9781118880173.ch4.
  15. Ya-Li Wang, Kai Sun, Yu-Bing Tu, Min-Long Tao, Zheng-Bo Xie, Hong-Kuan Yuan, Zu-Hong Xiong, Jun-Zhong Wang. Chirality switching of the self-assembled CuPc domains induced by electric field. Physical Chemistry Chemical Physics 2018, 20 (10) , 7125-7131. DOI: 10.1039/C7CP08279G.
  16. Francisco Zaera. Chirality in adsorption on solid surfaces. Chemical Society Reviews 2017, 46 (23) , 7374-7398. DOI: 10.1039/C7CS00367F.
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  18. Yoshito Tobe, Kazukuni Tahara, Steven De Feyter. Adaptive Building Blocks Consisting of Rigid Triangular Core and Flexible Alkoxy Chains for Self-Assembly at Liquid/Solid Interfaces. Bulletin of the Chemical Society of Japan 2016, 89 (11) , 1277-1306. DOI: 10.1246/bcsj.20160214.
  19. Xiaonan Sun, Fabien Silly, Francois Maurel, Changzhi Dong. Supramolecular chiral host–guest nanoarchitecture induced by the selective assembly of barbituric acid derivative enantiomers. Nanotechnology 2016, 27 (42) , 42LT01. DOI: 10.1088/0957-4484/27/42/42LT01.
  20. Karl‐Heinz Ernst. Molecular Chirality at Surfaces. 2016,,, 695-748. DOI: 10.1002/9783527680580.ch42.
  21. Shu-Ying Li, Ting Chen, Lin Wang, Dong Wang, Li-Jun Wan. Turning off the majority-rules effect in two-dimensional hierarchical chiral assembly by introducing a chiral mismatch. Nanoscale 2016, 8 (41) , 17861-17868. DOI: 10.1039/C6NR06341A.
  22. Lei Meng, Ye-Liang Wang, Li-Zhi Zhang, Shi-Xuan Du, Hong-Jun Gao. Fabrication and properties of silicene and silicene–graphene layered structures on Ir (111). Chinese Physics B 2015, 24 (8) , 086803. DOI: 10.1088/1674-1056/24/8/086803.
  23. Colin J. Murphy, Xuerong Shi, April D. Jewell, Allister F. McGuire, Darin O. Bellisario, Ashleigh E. Baber, Heather L. Tierney, Emily A. Lewis, David S. Sholl, E. Charles. H. Sykes. Impact of branching on the supramolecular assembly of thioethers on Au(111). The Journal of Chemical Physics 2015, 142 (10) , 101915. DOI: 10.1063/1.4907270.
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  25. Melissa R. Palmer, Justin M. Hagerman, Leigh M. Matano, Kelsey M. DeWitt, Yanjie Zhang. Thermodynamic analysis and fluorescence imaging of homochiral amino acid–amino acid interactions at the air/water interface. Journal of Colloid and Interface Science 2013, 408, 235-241. DOI: 10.1016/j.jcis.2013.07.020.
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  29. Christian Roth, Daniele Passerone, Karl-Heinz Ernst. Pasteur's quasiracemates in 2D: chiral conflict between structurally different enantiomers induces single-handed enantiomorphism. Chemical Communications 2010, 46 (45) , 8645. DOI: 10.1039/c0cc03060k.

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