Chiral and extended π-conjugated bis(2-pyridyl)phospholes as assembling N,P,N pincers for coordination-driven synthesis of supramolecular [2,2]paracyclophane analogues. - Université de Rennes Accéder directement au contenu
Article Dans Une Revue Chemistry - A European Journal Année : 2011

Chiral and extended π-conjugated bis(2-pyridyl)phospholes as assembling N,P,N pincers for coordination-driven synthesis of supramolecular [2,2]paracyclophane analogues.

Résumé

Chiral, π-conjugated 3,4-butano-1-phenyl-2,5-bis(2-pyridyl)phosphole derivatives 1a(2,2') and 1a(3) with chiral trans-1,2-diol moieties and fused pinene derivatives, respectively, were prepared from the corresponding chiral diynes by using the Fagan-Nugent method. Their UV/Vis absorption and chiroptical properties (optical rotation and circular dichroism) were studied. Their behavior as N,P,N chelates towards coordination of Cu(I) and formation of chiral supramolecular assemblies with π-conjugated ditopic dicyano ligands was investigated. Chiral C(2)-symmetric rectangles that are [2,2]paracyclophane analogues were obtained, as demonstrated by X-ray crystallography. During the course of this study, the first stable water-soluble phosphole derivative (1a(2)*2 HCl) was prepared. Furthermore, achiral 3,4-butano-1-phenyl-2,5-bis(aza[4]helicene)phosphole 1a(4) was synthesized and displays extended π conjugation. A supramolecular rectangle was obtained by coordination to Cu(I) and assembly with a dicyano stilbene. This coordination-driven supramolecular assembly contains a total of four aza[4]helicene moieties and displays two types of π-π stacking interactions in the solid state, that is, between two helicene moieties and between one helicene and a bridging dicyano ligand. All the supramolecular arrangements are discussed by comparing them with previous work on the parent 3,4-butano-1-phenyl-2,5-bis(2-pyridyl)phosphole.

Dates et versions

hal-00875454 , version 1 (22-10-2013)

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Citer

Ana Isabel Aranda Perez, Thomas Biet, Sébastien Graule, Tomohiro Agou, Christophe Lescop, et al.. Chiral and extended π-conjugated bis(2-pyridyl)phospholes as assembling N,P,N pincers for coordination-driven synthesis of supramolecular [2,2]paracyclophane analogues.. Chemistry - A European Journal, 2011, 17 (4), pp.1337-51. ⟨10.1002/chem.201001862⟩. ⟨hal-00875454⟩
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