[en] Two-dimensional (2D) chirality has been actively studied in view of numerous applications of chiral surfaces such as in chiral resolutions and enantioselective catalysis. Here, we report on the expression and amplification of chirality in hybrid 2D metallosupramolecular networks formed by a nucleobase derivative. Self-assembly of a guanine derivative appended with a pyridyl node was studied at the solution-graphite interface in the presence and absence of coordinating metal ions. In the absence of coordinating metal ions, a monolayer that is representative of a racemic compound was obtained. This system underwent spontaneous resolution upon addition of a coordinating ion and led to the formation of a racemic conglomerate. The spontaneous resolution could also be achieved upon addition of a suitable guest molecule. The mirror symmetry observed in the formation of the metallosupramolecular networks could be broken via the use of an enantiopure solvent, which led to the formation of a globally homochiral surface.
Research center :
CIRMAP - Centre d'Innovation et de Recherche en Matériaux Polymères
Disciplines :
Chemistry
Author, co-author :
Cucinotta, Antonino; Division of Molecular Imaging and Photonics, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, 3001 Leuven, Belgium
Kahlfuss, Christophe; CMC UMR 7140, Université de Strasbourg, CNRS, 4 Rue Blaise Pascal, F-67000 Strasbourg, France
Minoia, Andréa ; Université de Mons - UMONS > Faculté des Science > Service de Chimie des matériaux nouveaux
Eyley, Samuel ; Sustainable Materials Lab, Department of Chemical Engineering, KU Leuven, Campus Kulak Kortrijk, Etienne Sabbelaan 53, 8500 Kortrijk, Belgium
Zwaenepoel, Keanu; Division of Molecular Imaging and Photonics, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, 3001 Leuven, Belgium
Velpula, Gangamallaiah ; Division of Molecular Imaging and Photonics, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, 3001 Leuven, Belgium
Thielemans, Wim ; Sustainable Materials Lab, Department of Chemical Engineering, KU Leuven, Campus Kulak Kortrijk, Etienne Sabbelaan 53, 8500 Kortrijk, Belgium
Lazzaroni, Roberto ; Université de Mons - UMONS > Faculté des Science > Service de Chimie des matériaux nouveaux
Bulach, Véronique; CMC UMR 7140, Université de Strasbourg, CNRS, 4 Rue Blaise Pascal, F-67000 Strasbourg, France
Hosseini, Mir Wais; CMC UMR 7140, Université de Strasbourg, CNRS, 4 Rue Blaise Pascal, F-67000 Strasbourg, France
Mali, Kunal S ; Division of Molecular Imaging and Photonics, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, 3001 Leuven, Belgium
De Feyter, Steven ; Division of Molecular Imaging and Photonics, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, 3001 Leuven, Belgium
Language :
English
Title :
Metal Ion and Guest-Mediated Spontaneous Resolution and Solvent-Induced Chiral Symmetry Breaking in Guanine-Based Metallosupramolecular Networks.
R400 - Institut de Recherche en Science et Ingénierie des Matériaux
Funders :
Agentschap Innoveren en Ondernemen F?d?ration Wallonie-Bruxelles KU Leuven European Regional Development Fund Fonds Wetenschappelijk Onderzoek POM West-Vlaanderen Fonds De La Recherche Scientifique - FNRS
Funding text :
S.D.F. and K.S.M. gratefully acknowledge financial support from the Fund of Scientific Research Flanders (FWO) and KU Leuven–Internal Funds (C14/19/079). A.C. acknowledges financial support through an FWO Fellowship (1159922N). This work was in part supported by FWO and FNRS under EOS-CHISUB (40007495). The modeling studies are supported by FNRS (CECI, under Grant 2.5020.11) and by Wallonie (ZENOBE Tier-1 facility, grant 1117545). W.T. and S.E. thank Research Foundation Flanders (grant G0A1219N), KU Leuven (grant C14/18/061), and the European Union’s European Fund for Regional Development, Flanders Innovation & Entrepreneurship, and the Province of West-Flanders (Accelerate3 project, Interreg Vlaanderen-Nederland program) for financial support. The authors also thank Prof. Yves Geerts (Université Libre de Bruxelles-ULB) for providing purified sample of lead phthalocyanine.S.D.F. and K.S.M. gratefully acknowledge financial support from the Fund of Scientific Research Flanders (FWO) and KU Leuven-Internal Funds (C14/19/079). A.C. acknowledges financial support through an FWO Fellowship (1159922N). This work was in part supported by FWO and FNRS under EOS-CHISUB (40007495). The modeling studies are supported by FNRS (CECI, under Grant 2.5020.11) and by Wallonie (ZENOBE Tier-1 facility, grant 1117545). W.T. and S.E. thank Research Foundation Flanders (grant G0A1219N), KU Leuven (grant C14/18/061), and the European Union’s European Fund for Regional Development, Flanders Innovation & Entrepreneurship, and the Province of West-Flanders (Accelerate3 project, Interreg Vlaanderen-Nederland program) for financial support. The authors also thank Prof. Yves Geerts (Université Libre de Bruxelles-ULB) for providing purified sample of lead phthalocyanine.
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