Asymmetry Induction by Cooperative Intermolecular Hydrogen Bonds in Surface‐Anchored Layers of Achiral Molecules
Identifieur interne : 000248 ( France/Analysis ); précédent : 000247; suivant : 000249Asymmetry Induction by Cooperative Intermolecular Hydrogen Bonds in Surface‐Anchored Layers of Achiral Molecules
Auteurs : Alexandre Dmitriev [Suède] ; Hannes Spillmann ; Sebastian Stepanow ; Thomas Strunskus [Allemagne] ; Christof Wöll [Allemagne] ; Ari P. Seitsonen [France] ; Magali Lingenfelder ; Nian Lin [Allemagne] ; Johannes V. Barth [Suisse, Canada] ; Klaus Kern [Suisse]Source :
- ChemPhysChem [ 1439-4235 ] ; 2006-10-13.
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Abstract
The mesoscale induction of two‐dimensional supramolecular chirality (formation of 2D organic domains with a single handedness) was achieved by self‐assembly of 1,2,4‐benzenetricarboxylic (trimellitic) acid on a Cu(100) surface at elevated temperatures. The combination of spectroscopic [X‐ray photoelectron spectroscopy (XPS) and near‐edge X‐ray absorption fine structure (NEXAFS)], real‐space‐probe [scanning tunneling microscopy (STM)], and computational [density functional theory (DFT)] methods allows a comprehensive characterization of the obtained organic adlayers, where details of molecular adsorption geometry, intermolecular coupling, and surface chemical bonding are elucidated. The trimellitic acid species, comprising three functional carboxylic groups, form distinct stable mirror‐symmetric hydrogen‐bonded domains. The chiral ordering is associated with conformational restriction in the domains: molecules anchor to the substrate with an ortho carboxylate group, providing two para carboxylic acid moieties for collective lateral interweaving through H bonding, which induces a specific tilt of the molecular plane. The ease of molecular symmetry switching in domain formation makes homochiral‐signature propagation solely limited by the terrace width. The molecular layer modifies the morphology of the underlying copper substrate and induces μm‐sized strictly homochiral terraces.
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DOI: 10.1002/cphc.200600110
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The combination of spectroscopic [X‐ray photoelectron spectroscopy (XPS) and near‐edge X‐ray absorption fine structure (NEXAFS)], real‐space‐probe [scanning tunneling microscopy (STM)], and computational [density functional theory (DFT)] methods allows a comprehensive characterization of the obtained organic adlayers, where details of molecular adsorption geometry, intermolecular coupling, and surface chemical bonding are elucidated. The trimellitic acid species, comprising three functional carboxylic groups, form distinct stable mirror‐symmetric hydrogen‐bonded domains. The chiral ordering is associated with conformational restriction in the domains: molecules anchor to the substrate with an ortho carboxylate group, providing two para carboxylic acid moieties for collective lateral interweaving through H bonding, which induces a specific tilt of the molecular plane. The ease of molecular symmetry switching in domain formation makes homochiral‐signature propagation solely limited by the terrace width. The molecular layer modifies the morphology of the underlying copper substrate and induces μm‐sized strictly homochiral terraces.</div></front></TEI><affiliations><list><country><li>Allemagne</li><li>Canada</li><li>France</li><li>Suisse</li><li>Suède</li></country><region><li>Canton de Vaud</li><li>Île-de-France</li></region><settlement><li>Lausanne</li><li>Paris</li></settlement></list><tree><noCountry><name sortKey="Lingenfelder, Magali" sort="Lingenfelder, Magali" uniqKey="Lingenfelder M" first="Magali" last="Lingenfelder">Magali Lingenfelder</name><name sortKey="Spillmann, Hannes" sort="Spillmann, Hannes" uniqKey="Spillmann H" first="Hannes" last="Spillmann">Hannes Spillmann</name><name sortKey="Stepanow, Sebastian" sort="Stepanow, Sebastian" uniqKey="Stepanow S" first="Sebastian" last="Stepanow">Sebastian Stepanow</name></noCountry><country name="Suède"><noRegion><name sortKey="Dmitriev, Alexandre" sort="Dmitriev, Alexandre" uniqKey="Dmitriev A" first="Alexandre" last="Dmitriev">Alexandre Dmitriev</name></noRegion></country><country name="Allemagne"><noRegion><name sortKey="Strunskus, Thomas" sort="Strunskus, Thomas" uniqKey="Strunskus T" first="Thomas" last="Strunskus">Thomas Strunskus</name></noRegion><name sortKey="Lin, Nian" sort="Lin, Nian" uniqKey="Lin N" first="Nian" last="Lin">Nian Lin</name><name sortKey="Woll, Christof" sort="Woll, Christof" uniqKey="Woll C" first="Christof" last="Wöll">Christof Wöll</name></country><country name="France"><region name="Île-de-France"><name sortKey="Seitsonen, Ari P" sort="Seitsonen, Ari P" uniqKey="Seitsonen A" first="Ari P." last="Seitsonen">Ari P. 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