Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 139, Issue 25, Pages 8693-8697Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.7b04008
Keywords
-
Categories
Funding
- National Science Foundation of China [21371119, 21431004, 21401128, 21522104, 21620102001]
- National Key Basic Research Program of China [2014CB932102, 2016YFA 0203400]
- Shanghai Eastern Scholar Program
Ask authors/readers for more resources
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 C-3-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.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available