Research Progress of Macrocyclic Compounds in Highly Selective Molecular Imprinting Recognition System

doi:10.19894/j.issn.1000-0518.220142

Chinese Journal of Applied Chemistry ›› 2023, Vol. 40 ›› Issue (1): 24-39.DOI: 10.19894/j.issn.1000-0518.220142

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Research Progress of Macrocyclic Compounds in Highly Selective Molecular Imprinting Recognition System

Jing-Xia GAO, Zi-An WANG, Lian-Ming ZHANG(), Jian-Ping LI

College of Chemistry and Bioengineering，Guilin University of Technology，Guilin 541006，China

Received:2022-04-19 Accepted:2022-09-14 Published:2023-01-01 Online:2023-01-28
Contact: Lian-Ming ZHANG
About author:lianming226@126.com
Supported by:
the Guangxi Science and Technology Project(Guike AD19110059);the Guangxi Postgraduate Education Innovation Project(YCSW2022332)

Abstract

Abstract:

Molecular imprinting technology（MIT） has predetermination， recognition and usability， and has been widely used in chromatographic separation， solid phase extraction， drug analysis， chiral recognition and other fields. In recent years， researchers have introduced macrocyclic compounds into MIT， which not only increases the types of functional monomers， but also effectively improves the specificity of molecularly imprinted polymers and the selectivity of target molecules. In this paper， the research progress and application of macrocyclic compounds such as cyclodextrin， calixarene， pillararene， crown ether， cucurbituril and other supramolecular compounds in MIT in the past ten years are reviewed and its development prospects are prospected.

Key words: Microcylic compound, Molecular imprinting, Selectivity

CLC Number:

O654

Jing-Xia GAO, Zi-An WANG, Lian-Ming ZHANG, Jian-Ping LI. Research Progress of Macrocyclic Compounds in Highly Selective Molecular Imprinting Recognition System[J]. Chinese Journal of Applied Chemistry, 2023, 40(1): 24-39.

Figures/Tables 18

Fig.1 Schematic diagram of MIT［46］

Fig.2 Schematic representations of the general chemical structure（a）， the tridimensional structure of CD （b）， and chemical structure and dimensions for α-， β- and γ-CD （n=6， 7 and 8， respectively）（c）［50］

Fig.3 Schematic illustration of synthesis of β-CD based MIPs for carbendazim etermination［55］

Fig.4 Synthesis of derived β-CD-MIPs［58］

Fig.5 Preparation of MMIPs using CD-based ionic liquids as functional monomer for highly selective and effective enrichment of cytochrome c［64］

Fig.6 Specific recognition of protein by deep eutectic solvent-based magnetic β-CD-MIPs［69］

Fig.7 MIPs of CD supramolecular hydrogels improves drug loading and delivery［71］

Fig.8 Schematic representation of functionalized structures of CA［72］

Fig.9 Molecularly imprinted calixarene fiber for solid-phase microextraction of four organophosphorous pesticides in fruits［79］

Fig.10 Supramolecular imprinted electrochemical sensor for the neonicotinoid insecticide imidacloprid based on double amplification by Pt-In catalytic nanoparticles and a Bromophenol blue doped molecularly imprinted film［80］

Fig.11 MIPs with calix［4］arene derivative forthe recognition of acetanilide［81］

Fig.12 Structure of commonly CE［82］

Fig.13 The detailed illustration of the preparation of Fe3O4@SiO2@IIPs［86］

Fig.14 Multilayered IIPs with high selectivity towards Li+ based on the synergistic effect of 12-crown-4 and polyether sulfone［87］

Fig.15 X-ray crystal structures of CB［n］（n=5~8）［93］

Fig.16 Specific recognition of cationic paraquat in environmental water and vegetable samples by molecularly imprinted stir-bar sorptive extraction based on monohydroxylcucurbit［7］uril-paraquat inclusion complex［96］

Fig.17 Pillar［6］arene containing multilayer films： reversible uptake and release of guest molecules with methyl viologen moieties［113］

Table 1 Application of macrocyclic compounds in MIT

Macrocyclic compounds	Application mode	Reported applications	Deficiency
CD	Functional monomer， carrier	Metal ions， steroid molecules， pesticide residues， porphyrins， amino acids， oligopeptides， proteins， etc.	As anion receptors， CD and its derivatives are not easy to directly coated inorganic anions or positively charged receptors. It is difficult to maintain the activity of oligopeptides， proteins and other biological macromolecules in the elution process^{［54-71，115］}
CA	Functional monomer	Acetanilide， α-tocopherol， L-dopa and other chiral drugs， organic phosphorus pesticides such as methyl parathion and imidacloprid etc.	Because the structure of CA is wide at the top and narrow at the bottom， molecules are easy to fall off in the recognition process， and CA has poor water solubility^{［79-81， 116-117］}
CE	Functional monomer，Assisted recognition unit	K⁺， Rb⁺， Li⁺ and other alkali metal ions.	CE does not bind to anions. Due to the size of ring structure， CE is difficult to be applied to molecular recognition^{［86-92，118-120］}
CB	Functional monomer	Paraquat， melamine， quaternary ammonium salt and other pesticide molecules	CB has poor solubility and strong structural rigidity， so it cannot change its shape to suit the guest molecules. The separation and purification of CB［n］ is very difficult and not easy to be functionalized^［95-97］
PA	Assisted recognition unit	Methylviologen， 2-naphthoic acid pyrene， etc.	PA molecule has electron-rich cavity， highly symmetrical structure and strong rigidity^{［113-114］}

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Research Progress of Macrocyclic Compounds in Highly Selective Molecular Imprinting Recognition System

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