In situ growth of COF-rLZU1 on the surface of silica sphere as stationary phase for high performance liquid chromatography

Xu, Sen; Li, Zhouxian; Zhang, Lingyi; Zhang, Weibing; Li, Duxin

doi:10.1016/j.talanta.2020.121612

Cited by 40 publications

(19 citation statements)

References 28 publications

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“…Figure (c,d) shows the FTIR spectra for both COF1 and COF2 , the peak at 1606 cm –1 (−CN bond) could be detected, confirming the formation of a Schiff base in the COF synthesis. The peaks at around 1276 and 1579 cm –1 can be assigned to C–N and typical CC stretching vibration, respectively. − The solid state 13 C NMR spectrum also displayed the characteristic peak of carbon atoms of the imine bonds at ∼155 ppm (Figures S3 and S4 of the Supporting Information, SI). , Both FT-IR and solid-state 13 C NMR spectroscopies proved the formation of COF materials via Schiff-base condensation reaction.…”

Section: Resultsmentioning

confidence: 99%

Facile Synthesis of Rh Anchored Uniform Spherical COF for One-Pot Tandem Reductive Amination of Aldehydes to Secondary Imines

Wang

Liu

Tang

et al. 2021

ACS Appl. Mater. Interfaces

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The development of transition metal-based heterogeneous catalysts for economical and efficient synthesis of secondary imines remains both desirable and challenging. Herein, for the first time, we present two kinds of Rh nanoparticle anchored uniform spherical COF heterogeneous catalysts with well-defined crystalline structures for the effective one-pot tandem reductive amination of aldehydes on a gram scale. This reaction is carried out using ammonia as a nitrogen source and hydrogen gas as the source of hydrogen, which is not only an atom-economical but also an environmentally friendly process for the selective production of secondary imines. In particular, in the presence of the betterdesigned Rh nanoparticles anchored COF2 catalyst, the starting material aldehydes could be fully converted (99% conversion), and 95% selectivity of N-benzylidene(phenyl)methanamine is obtained under mild reaction conditions (2 MPa of H 2 and 90 °C). Additionally, the Rh/COF2 catalyst is also applied to a variety of substituted aromatic aldehyde compounds, manifesting good yields in corresponding secondary imines. This work not only expands the COF family but also offers economical and effective access to acquire various aromatic amine targets, especially secondary imines.

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Section: Resultsmentioning

confidence: 99%

Facile Synthesis of Rh Anchored Uniform Spherical COF for One-Pot Tandem Reductive Amination of Aldehydes to Secondary Imines

Wang

Liu

Tang

et al. 2021

ACS Appl. Mater. Interfaces

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“…Besides, COFs obtained from the traditional preparation methods often have irregular shapes, submicrometer size, and wide size distribution, causing low column efficiency and selectivity and high column backpressure of the COF-packed columns. ,, This is the greatest challenge for COFs used in HPLC. To overcome this drawback, in situ growth of COFs on silica microspheres has been explored for fabricating stationary phases, but it requires strict synthesis conditions and significantly increased monomer consumption …”

Section: Introductionmentioning

confidence: 99%

Are Highly Stable Covalent Organic Frameworks the Key to Universal Chiral Stationary Phases for Liquid and Gas Chromatographic Separations?

Chen

Jia

et al. 2022

J. Am. Chem. Soc.

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High-performance liquid chromatography (HPLC) and gas chromatography (GC) over chiral stationary phases (CSPs) represent the most popular and highly applicable technology in the field of chiral separation, but there are currently no CSPs that can be used for both liquid and gas chromatography simultaneously. We demonstrate here that two olefin-linked covalent organic frameworks (COFs) featuring chiral crown ether groups can be general CSPs for extensive separation not only in GC but also in normal-phase and reversed-phase HPLC. Both COFs have the same 2D layered porous structure but channels of different sizes and display high stability under different chemical environments including water, organic solvents, acids, and bases. Chiral crown ethers are periodically aligned within the COF channels, allowing for enantioselective recognition of guest molecules through intermolecular interactions. The COF-packed HPLC and GC columns show excellent complementarity and each affords high resolution, selectivity, and durability for the separation of a wide range of racemic compounds, including amino acids, esters, lactones, amides, alcohols, aldehydes, ketones, and drugs. The resolution performances are comparable to and the versatility is superior to those of the most widely used commercial chiral columns, showing promises for practical applications. This work thus advances COFs with high stability as potential universal CSPs for chromatography that are otherwise hard or impossible to produce.

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“…Using a β-CD-COF@SiO 2 HPLC column, excellent chiral recognition was obtained with good reproducibility for 24 pairs of chiral compounds . Using a similar in situ growth strategy, TpBD@SiO 2 , COF5@SiO 2 , BtaMth@SiO 2 , SiO 2 @rLZU1, CTpBD@SiO 2 , SiO 2 @COF, and MICOF@SiO 2 microspheres were fabricated and applied for HPLC separation. With the continuous expanding application of POPs in chromatographic packing, the core–shell structure of the combination of POPs and silica has become a new trend in the development of stationary phases.…”

Section: Introductionmentioning

confidence: 99%

Chromatographic Regulation by the Building Blocks for Triazine Polymer-Based Core–Shell Stationary Phases

Gao

Zuo

Han

et al. 2022

ACS Appl. Polym. Mater.

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Two versions of reversed-phase/hydrophilic interaction mixed-mode core–shell stationary phases for high-performance liquid chromatography using porous organic polymers as the shell material were investigated. The stationary phase named SiO2@CTPCC‑TPB using triazine-triphenylbenzene-based porous organic polymers as the shell material has been reported previously. To regulate chromatographic performance, heptazine–biphenyl moieties with fewer benzene rings and higher nitrogen content were used as organic building blocks to grow a porous shell on the surface of silica to acquire a core–shell stationary phase, namely, SiO2@CHPCy‑DB. Various techniques were used to characterize the developed core–shell microsphere, and nonpolar/polar solutes were utilized as probes to investigate the chromatographic behavior of the stationary phase. The results revealed that SiO2@CHPCy‑DB exhibited reversed-phase/hydrophilic interaction mixed-mode with multiple retention mechanisms. Meanwhile, the separation behavior of the two homemade columns and a commercial column was compared to assess the role of the building blocks in porous organic polymers in regulating and improving separation. The successful determination of drugs of abuse in urine via the SiO2@CHPCy‑DB column indicated its potential for the determination of trace analytes in complex samples.

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In situ growth of COF-rLZU1 on the surface of silica sphere as stationary phase for high performance liquid chromatography

Cited by 40 publications

References 28 publications

Facile Synthesis of Rh Anchored Uniform Spherical COF for One-Pot Tandem Reductive Amination of Aldehydes to Secondary Imines

Facile Synthesis of Rh Anchored Uniform Spherical COF for One-Pot Tandem Reductive Amination of Aldehydes to Secondary Imines

Are Highly Stable Covalent Organic Frameworks the Key to Universal Chiral Stationary Phases for Liquid and Gas Chromatographic Separations?

Chromatographic Regulation by the Building Blocks for Triazine Polymer-Based Core–Shell Stationary Phases

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