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Tabatchnik‐Rebillon, Alexandra; Aubé, Christophe; Bakkali, Hicham; Delaunay, Thierry; Manh, Gabriel Thia; Blot, Virginie; Thobie‐Gautier, Christine; Renault, Eric; Soulard, Marine; Planchat, Aurélien; Le Questel, Jean‐Yves; Le Guével, Rémy; Guguen‐Guillouzo, Christiane; Kauffmann, Brice; Ferrand, Yann; Huc, Ivan; Urgin, Karène; Condon, Sylvie; Léonel, Eric; Evain, Michel; Lebreton, Jacques; Jacquemin, Denis; Pipelier, Muriel; Dubreuil, Didier

Electrochemical Synthesis and Characterisation of Alternating Tripyridyl–Dipyrrole Molecular Strands with Multiple Nitrogen‐Based Donor–Acceptor Binding Sites

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  • Medientyp: E-Artikel
  • Titel: Electrochemical Synthesis and Characterisation of Alternating Tripyridyl–Dipyrrole Molecular Strands with Multiple Nitrogen‐Based Donor–Acceptor Binding Sites
  • Beteiligte: Tabatchnik‐Rebillon, Alexandra; Aubé, Christophe; Bakkali, Hicham; Delaunay, Thierry; Manh, Gabriel Thia; Blot, Virginie; Thobie‐Gautier, Christine; Renault, Eric; Soulard, Marine; Planchat, Aurélien; Le Questel, Jean‐Yves; Le Guével, Rémy; Guguen‐Guillouzo, Christiane; Kauffmann, Brice; Ferrand, Yann; Huc, Ivan; Urgin, Karène; Condon, Sylvie; Léonel, Eric; Evain, Michel; Lebreton, Jacques; Jacquemin, Denis; Pipelier, Muriel; Dubreuil, Didier
  • Erschienen: Wiley, 2010
  • Erschienen in: Chemistry – A European Journal
  • Sprache: Englisch
  • DOI: 10.1002/chem.201000859
  • ISSN: 0947-6539; 1521-3765
  • Schlagwörter: General Chemistry ; Catalysis ; Organic Chemistry
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  • Beschreibung: <jats:title>Abstract</jats:title><jats:p>Synthesis of alternating pyridine–pyrrole molecular strands composed of two electron‐rich pyrrole units (donors) sandwiched between three pyridinic cores (acceptors) is described. The envisioned strategy was a smooth electrosynthesis process involving ring contraction of corresponding tripyridyl–dipyridazine precursors. 2,6‐Bis[6‐(pyridazin‐3‐yl)]pyridine ligands <jats:bold>2 a</jats:bold>–<jats:bold>c</jats:bold> bearing pyridine residues at the terminal positions were prepared in suitable quantities by a Negishi metal cross‐coupling procedure. The yields of heterocyclic coupling between 2‐pyridyl zinc bromide reagents <jats:bold>12 a</jats:bold>–<jats:bold>c</jats:bold> and 2,6‐bis(6‐trifluoromethanesulfonylpyridazin‐3‐yl)pyridine increased from 68 to 95 % following introduction of electron‐donating methyl groups on the metallated halogenopyridine units. Favorable conditions for preparative electrochemical reduction of tripyridyl–dipyridazines <jats:bold>2 b</jats:bold>,<jats:bold>c</jats:bold> were established in THF/acetate buffer (pH 4.6)/acetonitrile to give the targeted 2,6‐bis[5‐(pyridin‐2‐yl)pyrrol‐2‐yl]pyridines <jats:bold>1 b</jats:bold> and <jats:bold>1 c</jats:bold> in good yields. The absorption behavior of the donor–acceptor tripyridyl–dipyrrole ligands was evaluated and compared to theoretical calculations. Highly fluorescent properties of these chromophores were found (<jats:italic>ν</jats:italic><jats:sub>em</jats:sub>≈2×10<jats:sup>4</jats:sup> cm<jats:sup>−1</jats:sup> in MeOH and CH<jats:sub>2</jats:sub>Cl<jats:sub>2</jats:sub>), and both pyrrolic ligands exhibit a remarkable quantum yield in CH<jats:sub>2</jats:sub>Cl<jats:sub>2</jats:sub> (<jats:italic>ϕ</jats:italic><jats:sub>f</jats:sub>=0.10). Structural studies in the solid state established the preferred <jats:italic>cis</jats:italic> conformation of the dipyrrolic ligands, which adopting a planar arrangement with an embedded molecule of water having a complexation energy exceeding 10 kcal mol<jats:sup>−1</jats:sup>. The ability of the tripyridyl–dipyrrole to complex two copper(II) ions in a pentacoordinate square was investigated.</jats:p>