Preparation of a photoresponsive molecularly imprinted polymer containing fluorine-substituted azobenzene chromophores

The primary objective of this work is to explore the photoresponsive molecular recognition directed by fluorine–fluorine interaction. A new kind of fluorine-substituted photoresponsive functional monomer, (4-methacryloyloxy) nonafluoroazobenzene (MANFAB), was designed and synthesized, and a photoresponsive molecularly imprinted polymer containing a fluorine-substituted azobenzene chromophore (MIPF) was then fabricated using MANFAB as the monomer and 2,3,4,5,7,8,9,10-octafluorophenazine (PAF) as the model template. The photoisomerization process of MIPF materials is reversible. The release and uptake of PAF from toluene is photoregulated by alternate irradiation at 315 nm and 440 nm, indicating that photoresponsive molecular recognition directed by fluorine–fluorine interaction is possible. The binding strength of the imprinted receptor sites in MIPF for PAF is 4.67 × 104 M−1. The density of receptor sites in the MIPF material is 1.26 μmol/g-MIPF.