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Chiral induction in covalent organic frameworks.

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.

SUBMITTER: Han X

PROVIDER: S-EPMC5882852 | biostudies-other | 2018 Apr

REPOSITORIES: biostudies-other

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Chiral induction in covalent organic frameworks.

Han Xing X Zhang Jie J Huang Jinjing J Wu Xiaowei X Yuan Daqiang D Liu Yan Y Cui Yong Y

Nature communications 20180403 1

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 C<sub>3</sub>-symmetric 1,3,5-triformylphloroglucinol (Tp) with diamine or triamine l ...[more]

PMID: 29615606

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Project description:Covalent organic frameworks (COFs) define a versatile structural paradigm combining attractive properties such as crystallinity, porosity, and chemical and structural modularity which are valuable for various applications. For the incorporation of COFs into optoelectronic devices, efficient charge carrier transport and intrinsic conductivity are often essential. Here, we report the synthesis of two imine-linked two-dimensional COFs, WTA and WBDT, featuring a redox-active Wurster-type motif based on the twisted tetragonal N,N,N',N'-tetraphenyl-1,4-phenylenediamine node. By condensing this unit with either terephthalaldehyde (TA) or benzodithiophene dialdehyde (BDT), COFs featuring a dual-pore kagome-type structure were obtained as highly crystalline materials with large specific surface areas and mesoporosity. In addition, the experimentally determined high conduction band energies of both COFs render them suitable candidates for oxidative doping. The incorporation of a benzodithiophene linear building block into the COF allows for high intrinsic macroscopic conductivity. Both anisotropic and average isotropic electrical conductivities were determined with van der Pauw measurements using oriented films and pressed pellets, respectively. Furthermore, the impact of different dopants such as F4TCNQ, antimony pentachloride and iodine on the conductivities of the resulting doped COFs was studied. By using the strong organic acceptor F4TCNQ, a massive increase of the radical cation density (up to 0.5 radicals per unit cell) and long-term stable electrical conductivity as high as 3.67 S m-1 were achieved for the anisotropic transport in an oriented film, one of the highest for any doped COF to date. Interestingly, no significant differences between isotropic and anisotropic charge transport were found in films and pressed pellets. This work expands the list of possible building nodes for electrically conducting COFs from planar systems to twisted geometries. The achievement of high and stable electrical conductivity paves the way for possible applications of new COFs in organic (opto)electronics.

Dataset Information

Chiral induction in covalent organic frameworks.

Publications

Chiral induction in covalent organic frameworks.

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