Homochiral 2D Porous Covalent Organic Frameworks for Heterogeneous Asymmetric Catalysis
Top Cited Papers
- 20 September 2016
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 138 (38), 12332-12335
- https://doi.org/10.1021/jacs.6b07714
Abstract
There have been breakthroughs in the development of covalent organic frameworks (COFs) with tunability of composition, structure, and function, but the synthesis of chiral COFs remains a great challenge. Here we report the construction of two-dimensional COFs with chiral functionalities embedded into the frameworks by imine condensations of enantiopure TADDOL-derived tetraaldehydes with 4,4'-diaminodiphenylmethane. Powder X-ray diffraction and computer modeling together with pore size distribution analysis show that one COF has a twofold-interpenetrated grid-type network and the other has a non-interpenetrated grid network. After postsynthetic modification of the chiral dihydroxy groups of TADDOL units with Ti(O(i)Pr)4, the materials are efficient and recyclable heterogeneous catalysts for asymmetric addition of diethylzinc to aldehydes with high enantioselectivity. The results reported here will greatly expand the scope of materials design and engineering for the creation of new types of functional porous materials.Keywords
Funding Information
- Ministry of Science and Technology of the People's Republic of China (2012CB8217, 2014CB932102)
- Shanghai Municipal Education Commission (SSTC-14YF1401300)
- National Natural Science Foundation of China (21371119, 21401128, 21431004, 21522104)
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