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Sterics and Hydrogen Bonding Control Stereochemistry and Self-Sorting in BINOL-Based Assemblies.
Zou, You-Quan; Zhang, Dawei; Ronson, Tanya K; Tarzia, Andrew; Lu, Zifei; Jelfs, Kim E; Nitschke, Jonathan R.
Afiliación
  • Zou YQ; Department of Chemistry, University of Cambridge, Cambridge CB2 1EW, United Kingdom.
  • Zhang D; Department of Chemistry, University of Cambridge, Cambridge CB2 1EW, United Kingdom.
  • Ronson TK; Department of Chemistry, University of Cambridge, Cambridge CB2 1EW, United Kingdom.
  • Tarzia A; Department of Chemistry, Molecular Sciences Research Hub, White City Campus, Imperial College London, London W12 0BZ, United Kingdom.
  • Lu Z; Department of Chemistry, University of Cambridge, Cambridge CB2 1EW, United Kingdom.
  • Jelfs KE; Department of Chemistry, Molecular Sciences Research Hub, White City Campus, Imperial College London, London W12 0BZ, United Kingdom.
  • Nitschke JR; Department of Chemistry, University of Cambridge, Cambridge CB2 1EW, United Kingdom.
J Am Chem Soc ; 143(24): 9009-9015, 2021 06 23.
Article en En | MEDLINE | ID: mdl-34124891
Here we demonstrate how the hydrogen-bonding ability of a BINOL-based dialdehyde subcomponent dictated the stereochemical outcome of its subsequent self-assembly into one diastereomeric helicate form when bearing free hydroxy groups, and another in the case of its methylated congener. The presence of methyl groups also altered the self-sorting behavior when mixed with another, short linear dialdehyde subcomponent, switching the outcome of the system from narcissistic to integrative self-sorting. In all cases, the axial chirality of the BINOL building block also dictated helicate metal center handedness during stereospecific self-assembly. A new family of stereochemically pure heteroleptic helicates were thus prepared using the new knowledge gained. We also found that switching from FeII to ZnII, or the incorporation of a longer linear ligand, favored heteroleptic structure formation.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: J Am Chem Soc Año: 2021 Tipo del documento: Article País de afiliación: Reino Unido Pais de publicación: Estados Unidos
Texto completo
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: J Am Chem Soc Año: 2021 Tipo del documento: Article País de afiliación: Reino Unido Pais de publicación: Estados Unidos