Progress in application of molecularly imprinted polymers based on β-cyclodextrin to environmental and food sample pretreatment

doi:10.3724/SP.J.1123.2019.06013

Abstract

Abstract:

β-cyclodextrin (β-CD) and its derivatives are an emerging class of functional monomers that find widespread use in molecular imprinting. It is well known that β-CD and its derivatives are capable of forming host-guest interaction inclusion complexes with many guest molecules. Molecularly imprinted polymers prepared via this type of interaction have the advantages of high stability and excellent selectivity. Therefore, β-CD-based molecularly imprinted polymers have attracted much attention and have been extensively developed for the selective separation and enrichment of target compounds in environmental and food samples with complex matrices. The objective of this review is to reveal the advantages of such molecularly imprinted polymers in complex sample pretreatment by reviewing the applications of molecularly imprinted polymers based on β-CD and its derivatives as functional monomers in environmental and food sample pretreatment since 2013.

Key words: molecular imprinting technique (MIT), sample pretreatment, β-cyclodextrin (β-CD), review

HE Zhongyu, CUI Yahan, HUANG Ning, YANG Shuliang, CHEN Yanhua, DING Lan. Progress in application of molecularly imprinted polymers based on β-cyclodextrin to environmental and food sample pretreatment[J]. Chinese Journal of Chromatography, 2020, 38(1): 104-112.

Figures/Tables 7

References

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Sample type	Target	Functional monomers	Crosslinker	Method for sample pretreatment	Reference
MAA-β-CD: methacrylic acid functionalized β-cyclodextrin; β-CD-1: mono-(6-N-allylamino-6-deoxy)-β-cyclodextrin; β-CD-2: mono-(6-N-diallylamine-6-deoxy)-β-cyclodextrin; β-CD-3: mono-(6-N-ethylenediamine (N-(2-bis(2-hydroxy-5-hexene))) (N-(2-hydroxy-5-hexene))-6-deoxy)-β-cyclodextrin; β-CD-4: mono-(6-N-ethylenediamine (N-(2-bis (2-hydroxy-7-octene))) (N-(2-hydroxy-7-octene))-6-deoxy)-β-cyclodextrin; β-CD: β-cyclodextrin; MA-β-CD: methylacryloyl-β-cyclodextrin; CTs: chitosan; TRIM: trimethylolpropane trimethacrylate; SPME: solid-phase microextraction; d-SPE: dispersive solid-phase extraction.
Tap and river waters	2, 4-dichlorophenol	MAA-β-CD	TRIM	SPE	^[28]
River water	p-nitrophenol	β-CD-1, β-CD-2, β-CD-3	EGDMA	SPME	^[29]
		and β-CD-4
Rain, river, and lake waters	di(2-ethylhexyl) phthalate	MA-β-CD	EGDMA	SPE	^[33]
Tap and river waters	2-aminopyridine	CTs and β-CD	EGDMA	d-SPE	^[40]

Sample type	Target	Functional monomers	Crosslinker	Method for sample pretreatment	Reference
MAA-β-CD: methacrylic acid functionalized β-cyclodextrin; β-CD-1: mono-(6-N-allylamino-6-deoxy)-β-cyclodextrin; β-CD-2: mono-(6-N-diallylamine-6-deoxy)-β-cyclodextrin; β-CD-3: mono-(6-N-ethylenediamine (N-(2-bis(2-hydroxy-5-hexene))) (N-(2-hydroxy-5-hexene))-6-deoxy)-β-cyclodextrin; β-CD-4: mono-(6-N-ethylenediamine (N-(2-bis (2-hydroxy-7-octene))) (N-(2-hydroxy-7-octene))-6-deoxy)-β-cyclodextrin; β-CD: β-cyclodextrin; MA-β-CD: methylacryloyl-β-cyclodextrin; CTs: chitosan; TRIM: trimethylolpropane trimethacrylate; SPME: solid-phase microextraction; d-SPE: dispersive solid-phase extraction.
Tap and river waters	2, 4-dichlorophenol	MAA-β-CD	TRIM	SPE	^[28]
River water	p-nitrophenol	β-CD-1, β-CD-2, β-CD-3	EGDMA	SPME	^[29]
		and β-CD-4
Rain, river, and lake waters	di(2-ethylhexyl) phthalate	MA-β-CD	EGDMA	SPE	^[33]
Tap and river waters	2-aminopyridine	CTs and β-CD	EGDMA	d-SPE	^[40]

Sample type	Target	Functional monomers	Crosslinker	Method for sample pretreatment	Reference
allyl-β-CD: allyl-β-cyclodextrin; β-CD-MA: β-cyclodextrin-maleic anhydride; DMC: [2-(methacryloyloxy) ethyl]trimethylammonium chloride; AN: acrylonitrile; AM: acrylamide; 4-VP: 4-vinylpyridine; A-β-CD: acryloyl-β-cyclodextrin; HMDI: 1, 6-hexamethylene diisocyanate; MBA: N, N-methylenebisacryl amide; TEOS: tetraethoxysilane; EDMA: ethylene glycol dimethacrylate.
Vegetables	pirimicarb	allyl-β-CD and MAA	EGDMA	SPE	^[13]
Strawberry	forchlorfenuron	β-CD	HMDI	QuEChERS	^[42]
Pork, beef, jelly, and	congo red	β-CD-MA and DMC	MBA	SPE	^[43]
hawthorn volumes
Pig livers	clenbuterol hydrochloride	allyl-β-CD and MAA	EGDMA	SPE	^[44]
Infant formula	di(2-ethylhexyl) phthalate	allyl-β-CD and AN	EGDMA	SPE	^[45]
Infant formula	di(2-ethylhexyl) phthalate	allyl-β-CD and AN	EGDMA	SPE	^[45]
Cinnamon and peppers	chlorpyrifos	β-CD and AM	TEOS	SPME	^[46]
Milk	bisphenol A	4-VP and β-CD	TRIM	SPE	^[48]
Citrus	benzimidazole	A-β-CD and MAA	EDMA	SPE	^[51]

Sample type	Target	Functional monomers	Crosslinker	Method for sample pretreatment	Reference
allyl-β-CD: allyl-β-cyclodextrin; β-CD-MA: β-cyclodextrin-maleic anhydride; DMC: [2-(methacryloyloxy) ethyl]trimethylammonium chloride; AN: acrylonitrile; AM: acrylamide; 4-VP: 4-vinylpyridine; A-β-CD: acryloyl-β-cyclodextrin; HMDI: 1, 6-hexamethylene diisocyanate; MBA: N, N-methylenebisacryl amide; TEOS: tetraethoxysilane; EDMA: ethylene glycol dimethacrylate.
Vegetables	pirimicarb	allyl-β-CD and MAA	EGDMA	SPE	^[13]
Strawberry	forchlorfenuron	β-CD	HMDI	QuEChERS	^[42]
Pork, beef, jelly, and	congo red	β-CD-MA and DMC	MBA	SPE	^[43]
hawthorn volumes
Pig livers	clenbuterol hydrochloride	allyl-β-CD and MAA	EGDMA	SPE	^[44]
Infant formula	di(2-ethylhexyl) phthalate	allyl-β-CD and AN	EGDMA	SPE	^[45]
Infant formula	di(2-ethylhexyl) phthalate	allyl-β-CD and AN	EGDMA	SPE	^[45]
Cinnamon and peppers	chlorpyrifos	β-CD and AM	TEOS	SPME	^[46]
Milk	bisphenol A	4-VP and β-CD	TRIM	SPE	^[48]
Citrus	benzimidazole	A-β-CD and MAA	EDMA	SPE	^[51]

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