Room temperature <i>in-situ</i> preparation of hydrazine-linked covalent organic frameworks coated capillaries for separation and determination of polycyclic aromatic hydrocarbons

doi:10.1007/s11705-022-2252-1

Front. Chem. Sci. Eng.

2023, Vol. 17

Issue (5) : 548-556 https://doi.org/10.1007/s11705-022-2252-1

RESEARCH ARTICLE

Room temperature in-situ preparation of hydrazine-linked covalent organic frameworks coated capillaries for separation and determination of polycyclic aromatic hydrocarbons

Yanli Zhang^1,², Wenjuan Lv^1,²(

), Fangling Wang^1,², Xiao Niu^1,², Guoxiu Wang^1,², Xuequan Wu^1,², Xiaoyun Zhang^1,²(

), Xingguo Chen^1,²

¹. State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China
². College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, China

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Abstract

Covalent organic frameworks (COFs) have been increasingly used in capillary electrochromatography due to their excellent characteristics. In this work, hydrazine-linked TFPB-DHzDS (TFPB: 1,3,5-tris(4-formylphenyl)benzene; DHzDS: 2,5-bis(3-(ethylthio)propoxy)terephthalohydrazide) was first synthesized by a simpler and easier method at room temperature and introduced into capillary electrochromatography as coating material. The TFPB-DHzDS coated capillaries were prepared by an in-situ growth process at room temperature. After optimizing the coating concentration and experimental conditions of capillary electrochromatography, baseline separation of two groups of polycyclic aromatic hydrocarbons was achieved based on the TFPB-DHzDS coated capillary. And the established method was used successfully to determine PAHs in natural water and soil samples. The spiked recoveries of polycyclic aromatic hydrocarbons in these samples ranged from 90.01% to 111.0%, indicating that the method is reliable and could detect polycyclic aromatic hydrocarbons in natural samples. Finally, molecular simulation was applied to study and visualize the interaction between the analytes and coating COF materials to investigate the molecular level separation mechanism further.

Keywords hydrazine-linked TFPB-DHzDS in-situ growth method open-tubular capillary electrochromatography molecular simulations

Corresponding Author(s): Wenjuan Lv,Xiaoyun Zhang

About author:

*These authors equally shared correspondence to this manuscript.

Online First Date: 23 February 2023 Issue Date: 28 April 2023

Cite this article:

Yanli Zhang,Wenjuan Lv,Fangling Wang, et al. Room temperature in-situ preparation of hydrazine-linked covalent organic frameworks coated capillaries for separation and determination of polycyclic aromatic hydrocarbons[J]. Front. Chem. Sci. Eng., 2023, 17(5): 548-556.

URL:

https://academic.hep.com.cn/fcse/EN/10.1007/s11705-022-2252-1
https://academic.hep.com.cn/fcse/EN/Y2023/V17/I5/548

Fig.1 Schematic diagram for the preparation of the TFPB-DHzDS coated capillary.

Fig.2 (a) PXRD, (b) FT-IR, and (c, d) SEM images of COF TFPB-DHzDS synthesized at room temperature; (c) at 10000 magnification and (d) at 30000 magnification.

Fig.3 SEM images of the inner walls of TFPB-DHzDS coated capillaries prepared at different pass-through monomer concentrations: (a) bare capillary; (b) 0.5 mg?mL^–1; (c) 1.0 mg?mL^–1; (d) 2.0 mg?mL^–1; (e) 4.0 mg?mL^–1; (f) 8.0 mg?mL^–1.

Fig.4 Effect of TFPB-DHzDS COFs coated capillaries with different monomer concentration for separation of PAHs. Operating conditions: 10 mmol?L^–1 borax, 32.5% acetonitrile, pH = 10.00 (0.5–4.0 mg?mL^–1); 10 mmol?L^–1 borax, 37.5% acetonitrile, pH = 10.00 (8.0 mg?mL^–1). Spectral peak designation: 1. NAP; 2. ANA; 3. ANT; 4. PHE; 5. PYR; 6. BPH. Operating voltage: +20 kV; detection wavelength: 226 nm.

Fig.5 (a, b) Comparison of the separation of the two groups PAHs based on the TFPB-DHzDS coated capillary; (c, d) based on the bare capillary and GLYMO-coated capillary. Conditions: 10 mmol?L^–1 borax with 27.5% acetonitrile, pH = 10.00 for (a) and (c); 10 mmol?L^–1 borax with 45.0% acetonitrile, pH = 10.50 for (b) and (d). Running voltage was +20 kV.

Tab.1 Linear range, linear equation, correlation coefficient, LOD and LOQ of PAHs

Fig.6 Electrophoretic spectra of two groups of PAHs based on TFPB-DHzDS coated capillary for 200 runs. Conditions: (a) 10 mmol?L^–1 borax with 32.5% acetonitrile, pH = 10.00; (b) 10 mmol?L^–1 borax with 45.0% acetonitrile, pH = 10.50. Running voltage: +20 kV; detection wavelength: 226 nm.

Fig.7 Molecular simulations of the interactions of ten PAHs with COF TFPB-DHzDS coated capillary column: (a) 1 NAP, 2 ANA, 3 PHE, 4 ANT, 5 PYR, 6 BPH; (b) 7 FLU, 8 FLT, 9 BaA, 10 BbF. Carbon atoms of COF TFPB-DHzDS were in cyan, nitrogen atoms in blue, oxygen atoms in red and hydrogen atoms in white; all PAHs molecules are shown in red; the binding energies between PAHs and COF TFPB-DHzDS are shown in blue.

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