Abstract
AbstractTo gain insight into chiral recognition in porous materials we have prepared a family of fourth generation chiral metal–organic frameworks (MOFs) that have rigid frameworks and adaptable (flexible) pores. The previously reported parent material, [Co2(S‐mandelate)2(4,4′‐bipyridine)3](NO3)2, CMOM‐1S, is a modular MOF; five new variants in which counterions (BF4−, CMOM‐2S) or mandelate ligands are substituted (2‐Cl, CMOM‐11R; 3‐Cl, CMOM‐21R; 4‐Cl, CMOM‐31R; 4‐CH3, CMOM‐41R) and the existing CF3SO3− variant CMOM‐3S are studied herein. Fine‐tuning of pore size, shape, and chemistry afforded a series of distinct host–guest binding sites with variable chiral separation properties with respect to three structural isomers of phenylpropanol. Structural analysis of the resulting crystalline sponge phases revealed that host–guest interactions, guest–guest interactions, and pore adaptability collectively determine chiral discrimination.
Highlights
The existence of chirality in biology makes the production of pure enantiomers important to the manufacture of pharmaceuticals, agrochemicals, flavorings, and fragrances
The powder X-ray diffraction (PXRD) patterns of as-synthesized chiral MOMs (CMOMs) (Supporting Information, Figures S1–S6) closely match those calculated from singlecrystal data
In each CMOM, adaptable pore size and shape resulted in tight binding sites that enable a variety of host—guest and guest–guest interactions
Summary
The existence of chirality in biology makes the production of pure enantiomers important to the manufacture of pharmaceuticals, agrochemicals, flavorings, and fragrances. The resulting family of CMOMs detailed exhibits a hard rigid framework and adaptable or soft pores.[13] These materials can be classified as a fourth-generation MOFs.[14] The parent CMOM, CMOM-1S, can be readily fine-tuned through substitution of the counterion (BF4À, CMOM-2S; CF3SO3À, CMOM-3S) or linker ligand (2-Cl, CMOM-11R; 3-Cl, CMOM-21R; 4-Cl, CMOM-31R; 4-CH3, CMOM-41R) As detailed below, this family of CMOMs can serve as chiral crystalline sponges (CCSs) to provide structural insight into the supramolecular interactions that occur between phenylpropanols and the pore surface of this family of CMOMs
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