Structural modifications, metal coordination and self-assembly of quinoline oligoamide foldamers

Abstract : Oligo-quinolinecarboxamide foldamers form stable helical structures in solution and in the solid state. These helices are stabilized by hydrogen bonds, π-π stacking and electrostatic interactions. In a first part of this manuscript, vinyl functions have been introduced as isosteres of amides. The resulting quinolylene-vinylene oligomers form mainly extended structures in solution. Helical folded conformations can nevertheless be stabilized by attaching two segments of oligoamides at both ends of an oligoquinolylene-vinylene. In a second part, copper (II) ions have been loaded into the single helices of quinolinecarboxamide foldamers. The copper (II) ions coordinate the nitrogen atoms of the quinoline units and also deprotonated amide nitrogen atoms. A one dimensional alignment of the copper (II) ions was observed in the solid state. In a third part, acridine functionalized foldamers were prepared in order to test their self-assembly into bundles through interactions between aromatic functions at the exterior of helices. Associations of the acridine functionalized oligoamides are weak in organic solution. In contrast, in the solid state, interactions between helices are mainly governed by acridine units. In a fourth part, metal coordination has been used to promote helix-helix assembly of quinoline oligoamides foldamers. Acridine and pyridine rings have been attached on the side chains of these oligomers to allow coordination with metals, palladium (II) in this case. The helix-helix assembly of quinoline oligoamides by palladium coordination has been confirmed by NMR and x-ray diffraction.
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Jinhua Wang. Structural modifications, metal coordination and self-assembly of quinoline oligoamide foldamers. Organic chemistry. Université de Bordeaux, 2019. English. ⟨NNT : 2019BORD0122⟩. ⟨tel-02304822⟩

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