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Sterics and hydrogen bonding control stereochemistry and self-sorting in binol-based assemblies

DOI: 10.1021/jacs.1c05172 DOI Help

Authors: You-Quan Zou (University of Cambridge) , Dawei Zhang (University of Cambridge) , Tanya K. Ronson (University of Cambridge) , Andrew Tarzia (Imperial College London) , Zifei Lu (University of Cambridge) , Kim E. Jelfs (Imperial College London) , Jonathan R. Nitschke (University of Cambridge)
Co-authored by industrial partner: No

Type: Journal Paper
Journal: Journal Of The American Chemical Society , VOL 71

State: Published (Approved)
Published: June 2021
Diamond Proposal Number(s): 21497

Open Access Open Access

Abstract: 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.

Journal Keywords: Self organization; Supramolecular structures and assemblies; Metals; Ligands; Iron-sulfur clusters

Subject Areas: Chemistry

Instruments: I19-Small Molecule Single Crystal Diffraction


Discipline Tags:

Organic Chemistry Chemistry

Technical Tags:

Diffraction Single Crystal X-ray Diffraction (SXRD)