Related Experiment Video
Updated: Mar 1, 2026

Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks MOFs
Published on: January 17, 2020
Chiral Covalent Organic Frameworks with High Chemical Stability for Heterogeneous Asymmetric Catalysis
Xing Han1, Qingchun Xia1, Jinjing Huang1
1School of Chemistry and Chemical Engineering and State Key Laboratory of Metal Matrix Composites, Shanghai Jiao Tong University , Shanghai 200240, China.
Abstract:
Covalent organic frameworks (COFs) featuring chirality, stability, and function are of both fundamental and practical interest, but are yet challenging to achieve. Here we reported the metal-directed synthesis of two chiral COFs (CCOFs) by imine-condensations of enantiopure 1,2-diaminocyclohexane with C3-symmetric trisalicylaldehydes having one or zero 3-tert-butyl group. Powder X-ray diffraction and modeling studies, together with pore size distribution analysis demonstrate that the Zn(salen)-based CCOFs possess a two-dimensional hexagonal grid network with AA stacking. Dramatic enhancement in the chemical stability toward acidic (1 M HCl) and basic (9 M NaOH) conditions was observed for the COF incorporated with tert-butyl groups on the pore walls compared to the nonalkylated analog. The Zn(salen) modules in the CCOFs allow for installing multivariate metals into the frameworks by postsynthetic metal exchange. The exchanged CCOFs maintain high crystallinity and porosity and can serve as efficient and recyclable heterogeneous catalysts for asymmetric cyanation of aldehydes, Diels-Alder reaction, alkene epoxidation, epoxide ring-opening, and related sequential reactions with up to 97% ee.
More Related Videos
Related Concept Videos
Heterogeneous Catalysis
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
Catalysis
Molecules with Multiple Chiral Centers
Prochirality
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

