Allyl-β-cyclodextrin

Zhao Y, et al. Microchemical Journal, 2021, 168, 106462.

A monolithic stationary phase based on allyl-β-cyclodextrin was developed via in situ free-radical polymerization for high-performance liquid chromatography (HPLC) separation of lipopeptide antibiotics. The synthesis involved co-polymerization of allyl-β-cyclodextrin and methyl methacrylate (MMA) as functional monomers, with triallyl isocyanurate (TAIC) and ethylene glycol dimethacrylate (EDMA) serving as dual cross-linkers. The reaction was initiated by azobisisobutyronitrile (AIBN) and conducted within a stainless steel column pre-packed with a ternary porogenic system comprising 1,4-butanediol (BDO), N,N-dimethylformamide (DMF), and 1-dodecanol.
This formulation yielded a series of monoliths (M1-M8) optimized for porosity and mechanical strength. The resulting monolithic column exhibited a highly porous, interconnected structure ideal for chromatographic applications. Its cyclodextrin-derived cavities enhanced host-guest interactions, enabling selective and efficient retention of structurally diverse lipopeptide antibiotics.

Zhang X, et al. Journal of Chromatography B, 2022, 1193, 123172.

This study demonstrates the successful use of allyl-β-cyclodextrin (allyl-β-CD) as a functional monomer for the synthesis of molecularly imprinted polymers (MIPs) tailored for arctiin recognition. The arctiin-imprinted monoliths were fabricated by in situ polymerization within stainless-steel tubes. A defined amount (10 mg) of allyl-β-CD was first dissolved in 100 μL of DMF. The template molecule arctiin, along with 4-vinylpyridine (4-VP) and the radical initiator AIBN, was sequentially added. Crosslinking was achieved using ethylene glycol dimethacrylate (EDMA), and the porogenic solvents DMF and toluene were incorporated to facilitate polymer network formation.
Polystyrene (PS) was included at varying concentrations to modulate the monolithic structure. The mixture was subjected to ultrasonic dispersion and transferred into stainless-steel tubes, followed by polymerization at 60 °C for 12 hours. Post-polymerization, unreacted components and template residues were effectively removed using toluene and a methanol-acetic acid solution (9:1, v/v). Non-imprinted control monoliths were synthesized in parallel under identical conditions, excluding the template molecule.

Kang Y, et al. Carbohydrate Polymers, 2012, 88(2), 459-464.

A novel class of molecularly imprinted polymers (MIPs) was synthesized using allyl-β-cyclodextrin (allyl-β-CD) as a binary functional monomer in conjunction with methacrylic acid (MAA), specifically designed for the selective adsorption of phthalate compounds. The preparation began with the allylation of β-cyclodextrin. In detail, 2.29 g of β-CD was dissolved in anhydrous DMF, and 0.25 g of NaH was introduced under a nitrogen atmosphere. After the evolution of hydrogen ceased, excess NaH was filtered off, and the filtrate was reacted with 0.5 mL of allylic bromide at room temperature under nitrogen protection for 24 hours to yield allyl-β-CD.
Subsequently, 2 mmol of the template molecule dipropyl phthalate (DPP), 12 mmol of MAA, 60 mmol of crosslinker ethylene dimethacrylate (EDMA), and 40 mg of the radical initiator AIBN were added to the solution. Polymerization was carried out at 60 °C for 24 hours under nitrogen atmosphere. The resulting polymer was ground, and particles within the 200-400 mesh size range were collected.