Chiral induction in covalent organic frameworks

Xing Han, Jie Zhang, Jinjing Huang, Xiaowei Wu, Daqiang Yuan, Yan Liu () and Yong Cui ()
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Xing Han: Shanghai Jiao Tong University
Jie Zhang: Shanghai Jiao Tong University
Jinjing Huang: Shanghai Jiao Tong University
Xiaowei Wu: Shanghai Jiao Tong University
Daqiang Yuan: Chinese Academy of Sciences
Yan Liu: Shanghai Jiao Tong University
Yong Cui: Shanghai Jiao Tong University

Nature Communications, 2018, vol. 9, issue 1, 1-10

Abstract: Abstract Synthetic control over chirality and function is the crowning achievement for metal-organic frameworks, but the same level of control has not been achieved for covalent organic frameworks (COFs). Here we demonstrate chiral COFs (CCOFs) can be crystallized from achiral organic precursors by chiral catalytic induction. A total of nine two-dimensional CCOFs are solvothermally prepared by imine condensations of the C3-symmetric 1,3,5-triformylphloroglucinol (Tp) with diamine or triamine linkers in the presence of catalytic amount of (R)- or (S)-1-phenylethylamine. Homochirality of these CCOFs results from chiral catalyst-induced immobilization of threefold-symmetric tris(N-salicylideneamine) cores with a propeller-like conformation of one single handedness during crystallization. The CCOF-TpTab showed high enantioselectivity toward chiral carbohydrates in fluorescence quenching and, after postsynthetic modification of enaminone groups located in chiral channels with Cu(II) ions, it can also be utilized as a heterogeneous catalyst for the asymmetric Henry reaction of nitroalkane with aldehydes.

Date: 2018
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DOI: 10.1038/s41467-018-03689-9

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