Preparation of two kinds of porphyrin‐functionalized polymeric materials based on poly(glyceryl methacrylate)

Poly(glyceryl methacrylate) (PGMA) was reacted with meso‐tetra(4‐hydroxylphenyl)porphyrin (THPP) in a homogeneous system via the ring opening reaction between epoxy and hydroxyl groups, which exist on the side chain of PGMA and the outside ring of THPP, respectively. Porphyrin‐functionalized PGMA with line‐type (denoted as HPP‐PGMA), on whose side chains hydroxylphenyl porphyrin (HPP) was bonded, was obtained. Grafting particles PGMA/SiO₂ were also reacted with THPP, and the porphyrin‐immobilized particles (denoted as HPP‐PGMA/SiO₂), on which HPP was supported, were produced. The above two target products were characterized using spectroscopy methods, such as infrared (IR), nuclear magnetic resonance (¹H‐NMR), electronic absorption, and fluorescence emission. The effects of various factors on the bonding and immobilization reactions of HPP were studied in detail. The experimental results show that the soluble HPP‐PGMA has all the spectral characteristics of porphyrins and the absorption or emission intensity is increased with the increase in the bonding degree of HPP. In the preparation process of HPP‐PGMA, in order to avoid the occurrence of the crosslinking reaction and to obtain HPP‐PGMA with complete line‐type, the catalyst should be selected and the reaction time should be controlled. NaHCO₃ is an appropriate catalyst. In the immobilization process of HPP on the grafting particle PGMA/SiO₂, the greater the used amount of the catalyst triethylamine (TEA), the more rapid is the rate of ring opening reaction, resulting in higher immobilization amount of HPP. Besides, the immobilization amount of HPP is increased with the enhancement of the reaction temperature. Copyright © 2008 John Wiley & Sons, Ltd.