From One-Dimensional Disordered Racemate to Ordered Racemic Conglomerates through Metal-Coordination-Driven Self-Assembly at the Liquid-Solid Interface.
[en] In recent years, there has been significant focus on investigating and controlling chiral self-assembly, specifically in the context of enantiomeric separation. This study explores the self-assembly behavior of 4-dodecyl-3,6-di(2-pyridyl)pyridazine (DPP-C12) at the interface between heptanoic acid (HA) and highly oriented pyrolytic graphite (HOPG) using a combination of scanning tunneling microscopy (STM) and multiscale molecular modeling. The self-assembled monolayer structure formed by DPP-C12 is periodic in one direction, but aperiodic in the direction orthogonal to it. These structures resemble 1D disordered racemic compounds. Upon introducing palladium [Pd(II)] ions, complexing with DPP-C12, these 1D disordered racemic compounds spontaneously transform into 2D racemic conglomerates, which is rationalized with the assistance of force-field simulations. Our findings provide insights into the regulation of two-dimensional chirality.
Research center :
CIRMAP - Centre d'Innovation et de Recherche en Matériaux Polymères
Disciplines :
Chemistry
Author, co-author :
Hu, Tianze ✱; KU Leuven, Division of Molecular Imaging and Photonics, Department of Chemistry, Celestijnenlaan 200F, 3001, Leuven, Belgium
Minoia, Andréa ✱; Université de Mons - UMONS > Faculté des Science > Service de Chimie des matériaux nouveaux
Velpula, Gangamallaiah; KU Leuven, Division of Molecular Imaging and Photonics, Department of Chemistry, Celestijnenlaan 200F, 3001, Leuven, Belgium
Ryskulova, Kanykei; Supramolecular Chemistry Group, Centre of Macromolecular Chemistry, Department of Organic and Macromolecular Chemistry, Ghent University, Krijgslaan 281 S4, 9000, Ghent, Belgium
Van Hecke, Kristof; XStruct, Department of Chemistry, Ghent University, Krijgslaan 281 S3, 9000, Ghent, Belgium
Lazzaroni, Roberto ; Université de Mons - UMONS > Faculté des Science > Service de Chimie des matériaux nouveaux
Mali, Kunal S; KU Leuven, Division of Molecular Imaging and Photonics, Department of Chemistry, Celestijnenlaan 200F, 3001, Leuven, Belgium
Hoogenboom, Richard; Supramolecular Chemistry Group, Centre of Macromolecular Chemistry, Department of Organic and Macromolecular Chemistry, Ghent University, Krijgslaan 281 S4, 9000, Ghent, Belgium
De Feyter, Steven; KU Leuven, Division of Molecular Imaging and Photonics, Department of Chemistry, Celestijnenlaan 200F, 3001, Leuven, Belgium
✱ These authors have contributed equally to this work.
Language :
English
Title :
From One-Dimensional Disordered Racemate to Ordered Racemic Conglomerates through Metal-Coordination-Driven Self-Assembly at the Liquid-Solid Interface.
Publication date :
15 October 2023
Journal title :
Chemistry
ISSN :
0947-6539
eISSN :
1521-3765
Publisher :
John Wiley and Sons Inc, Germany
Pages :
e202302545
Peer reviewed :
Peer Reviewed verified by ORBi
Research unit :
S817 - Chimie des matériaux nouveaux
Research institute :
R400 - Institut de Recherche en Science et Ingénierie des Matériaux
Funders :
Fonds Wetenschappelijk Onderzoek China Scholarship Council Fonds De La Recherche Scientifique - FNRS Waalse Gewest
Funding text :
Financial support from the Research Foundation – Flanders (FWO G0 A3220 N) and KU Leuven‐Internal Funds (C14/19/079) is acknowledged. This work was in part supported by FWO (G0H2122 N, GF9118 N) and F.R.S.‐FNRS under the Excellence of Science EOS program (projects 30489208 and 40007495). The computational resources in Mons are supported by the FNRS “Consortium des Equipements de Calcul Intensif−CECI” program Grant No. 2.5020.11 and by the Walloon Region (ZENOBE Tier‐1 supercomputer, under grant 1117545). T.H. acknowledges the China Scholarship Council (CSC) (No. 202006150018). GM.V. acknowledges the FWO fellowship award (No. 1269221 N). RH acknowledges FWO for financial support through the Wetenschappelijke Onderzoeksgemeenschaap (WOG) supramolecular chemistry and materials. K.V.H thanks the Research Foundation, Flanders (FWO) (project AUGE/11/029).
K. S. Mali, N. Pearce, S. De Feyter, N. R. Champness, Chem. Soc. Rev. 2017, 46, 2520–2542;
W. Li, J. Zhou, S. Cai, Z. Yu, J. Zhang, N. Fang, T. Li, Y. Wu, T. Chen, X. Xie, H. Ma, K. Yan, N. Dai, X. Wu, H. Zhao, Z. Wang, D. He, L. Pan, Y. Shi, P. Wang, W. Chen, K. Nagashio, X. Duan, X. Wang, Nat. Electron. 2019, 2, 563–571;
J. A. Berrocal, G. H. Heideman, B. F. M. de Waal, M. Enache, R. W. A. Havenith, M. Stöhr, E. W. Meijer, B. L. Feringa, J. Am. Chem. Soc. 2020, 142, 4070–4078.
R. Yi, Y. Mao, Y. Shen, L. Chen, J. Am. Chem. Soc. 2021, 143, 12897–12912.
B. Daelemans, S. Eyley, C. Marquez, V. Lemmens, D. E. De Vos, W. Thielemans, W. Dehaen, S. De Feyter, Chem. Sci. 2022, 13, 9035–9046.
T. Zhang, Z. Cheng, Y. Wang, Z. Li, C. Wang, Y. Li, Y. Fang, Nano Lett. 2010, 10, 4738–4741.
S. De Feyter, F. C. De Schryver, Chem. Soc. Rev. 2003, 32, 139–150;
J. A. Theobald, N. S. Oxtoby, M. A. Phillips, N. R. Champness, P. H. Beton, Nature 2003, 424, 1029;
A. Ciesielski, P. J. Szabelski, W. Rżysko, A. Cadeddu, T. R. Cook, P. J. Stang, P. Samorì, J. Am. Chem. Soc. 2013, 135, 6942–6950.
A. Cucinotta, C. Kahlfuss, A. Minoia, S. Eyley, K. Zwaenepoel, G. Velpula, W. Thielemans, R. Lazzaroni, V. Bulach, M. W. Hosseini, K. S. Mali, S. De Feyter, J. Am. Chem. Soc. 2023, 145, 1194–1205;
M.-A. Carvalho, H. Dekkiche, M. Nagasaki, Y. Kikkawa, R. Ruppert, J. Am. Chem. Soc. 2019, 141, 10137–10141;
L. Dong, Z. A. Gao, N. Lin, Prog. Surf. Sci. 2016, 91, 101–135.
R. E. Sikma, K. P. Balto, J. S. Figueroa, S. M. Cohen, Angew. Chem. Int. Ed. 2022, 61, e202206353.
Q. Xue, N. Xue, J. Li, Y. Li, R. Li, Y. Zhang, N. Li, Z. Shen, S. Hou, Y. Wang, J. Phys. Chem. C 2020, 124, 7790–7796.
J. R. L. Hong-Cai Zhou, O. M. Yaghi, Chem. Rev. 2012, 112, 673–674;
S. L. Griffin, N. R. Champness, Coord. Chem. Rev. 2020, 414, 213295;
J. V. Barth, G. Costantini, K. Kern, Nature 2005, 437, 671–679;
J. Liu, M. Abel, N. Lin, J. Phys. Chem. Lett. 2022, 13, 1356–1365.
P. Messina, A. Dmitriev, N. Lin, H. Spillmann, M. Abel, J. V. Barth, K. Kern, J. Am. Chem. Soc. 2002, 124, 14000–14001;
A. Dmitriev, H. Spillmann, M. Lingenfelder, N. Lin, J. V. Barth, K. Kern, Langmuir 2004, 20, 4799–4801.
S. De Feyter, M. M. S. Abdel-Mottaleb, N. Schuurmans, B. J. V. Verkuijl, J. H. van Esch, B. L. Feringa, F. C. De Schryver, Chem. Eur. J. 2004, 10, 1124–1132;
X. Sun, X. Yao, F. Lafolet, G. Lemercier, J.-C. Lacroix, J. Phys. Chem. Lett. 2019, 10, 4164–4169.
