Homochiral 2D Porous Covalent Organic Frameworks for Heterogeneous Asymmetric Catalysis
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 int...
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| Published in | Journal of the American Chemical Society Vol. 138; no. 38; pp. 12332 - 12335 |
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| Main Authors | , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
United States
American Chemical Society
28.09.2016
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| Subjects | |
| Online Access | Get full text |
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| 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. |
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| AbstractList | 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(OⁱPr)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. 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. 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. 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.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. |
| Author | Liu, Yan Cui, Yong Han, Xing Zhang, Jie Wu, Xiaowei Wang, Xiuren |
| AuthorAffiliation | Collaborative Innovation Center of Chemical Science and Engineering School of Chemistry and Chemical Engineering and State Key Laboratory of Metal Matrix Composites Shanghai Jiao Tong University |
| AuthorAffiliation_xml | – name: School of Chemistry and Chemical Engineering and State Key Laboratory of Metal Matrix Composites – name: Shanghai Jiao Tong University – name: Collaborative Innovation Center of Chemical Science and Engineering |
| Author_xml | – sequence: 1 givenname: Xiuren surname: Wang fullname: Wang, Xiuren – sequence: 2 givenname: Xing surname: Han fullname: Han, Xing – sequence: 3 givenname: Jie surname: Zhang fullname: Zhang, Jie – sequence: 4 givenname: Xiaowei surname: Wu fullname: Wu, Xiaowei – sequence: 5 givenname: Yan surname: Liu fullname: Liu, Yan email: liuy@sjtu.edu.cn – sequence: 6 givenname: Yong surname: Cui fullname: Cui, Yong email: yongcui@sjtu.edu.cn |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/27618953$$D View this record in MEDLINE/PubMed |
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