Preparation of Photoirradiation Molecular Imprinting Polymer for Selective Separation of Branched Cyclodextrins

Molecules. 2017 Feb 21;22(2):288. doi: 10.3390/molecules22020288.

Abstract

In the present study, photoirradiation molecularly imprinted polymer (MIP) with azobenzene was used as a functional monomer for the selective separation of the branched cyclodextrins. The functional monomer 4-methacryloyloxy azobenzene (MAA) and the molecular template 6-O-α-d-maltosyl-β-cyclodextrin (G2-β-CD) were implemented for the molecular imprinting. The core-shell structure of photoirradiation MIP was visualized by the transmission electron microscopy (TEM). With Fourier transform infrared spectroscopy (FTIR) and thermogravimetric analysis (TGA), we identified that G2-β-CD was imprinted into the polymer and removed from the MIP. The binding association constant (Ka) and the maximum number of the binding site (Nmax) were 1.72 × 10⁴ M-1 and 7.93 μmol·g-1 MIP, respectively. With alternate irradiation at 365 and 440 nm light, the prepared MIP reversibly released and rebound to the G2-β-CD, which resulted in the nearly zero amount of G2-β-CD in the solution. The HPLC results indicated that the purity of G2-β-CD could reach 90.8% after going through MIP. The main finding of our study was that the photoirradiation of MIP was an easy and effective method for the selective separation of the branched cyclodextrins.

Keywords: azobenzene derivatives; branched cyclodextrins; molecular imprinting polymer; photoirradiation.

MeSH terms

  • Cyclodextrins / chemistry*
  • Isomerism
  • Light*
  • Microscopy, Electron
  • Molecular Imprinting* / methods
  • Polymers / chemical synthesis
  • Polymers / chemistry*
  • Proton Magnetic Resonance Spectroscopy
  • Radiation*
  • Spectroscopy, Fourier Transform Infrared
  • Thermogravimetry

Substances

  • Cyclodextrins
  • Polymers