Acta Phys. -Chim. Sin. ›› 2009, Vol. 25 ›› Issue (02): 341-346.doi: 10.3866/PKU.WHXB20090225

• ARTICLE • Previous Articles     Next Articles

Simultaneous Synthesis and Linkage of Porphyrin onto Side Chain of Copolymer P(GMA-co-MMA)

WANG Fei-Yu; GAO Bao-Jiao; WANG Rui-Xin   

  1. Department of Chemical Engineering, North University of China, Taiyuan 030051, P. R. China
  • Received:2008-08-15 Revised:2008-10-10 Published:2009-01-16
  • Contact: GAO Bao-Jiao

Abstract: The copolymerization of glyceryl methacrylate (GMA) and methyl methacrylate (MMA) was conducted in a solution polymerization systemresulting in the formation of copolymerP (GMA-co-MMA). Parahydroxybenzaldehyde was then bound to the side chains of P(GMA-co-MMA) via ring-opening and ether-forming reactions of the epoxy groups on P(GMA-co-MMA). A benzaldehyde (BA)-bound copolymer BA-P(GMA-co-MMA) was thus prepared. The simultaneous synthesis and linkage of the porphyrin onto the side chains of P(GMA-co-MMA) was realized successfully using the Adler method in a homogeneous system. Benzaldehyde, BA-P(GMA-co-MMA), and pyrrole were used as reactants, resulting in the porphyrin (PP)-functionalized line-type macromolecule PP-P(GMA-co-MMA). The chemical structure of PP-P(GMA-co-MMA) was characterized by Fourier transform infrared (FTIR) spectroscopy and nuclear magnetic resonance (1H-NMR) spectroscopy. The spectral properties of PP-P(GMA-co-MMA) were studied and its photophysical behavior was investigated in depth. Experimental results show that PP-P(GMA-co-MMA) has the same electronic absorption spectrum and fluorescence emission spectrum as tetraphenyl porphyrin. In the electronic absorption spectra of PP-P(GMA-co-MMA) both the Soret absorption band and the Q absorption band strengthen as the amount of bound porphyrin increaseds. The Q emission band intensity of PP-P(GMA-co-MMA) also first increases with the increase of the amount of bound porphyrin until to a maximum, and then decreases if more porphyrin units are present. Intramolecular energy transfer of the macromolecule PP-P(GMA-co-MMA) should be responsible for this behavior.

Key words: Phenyl porphyrin, Glyceryl methacrylate, Porphyrin-functionalized polymer, Synchronistic synthesis and linkage, Spectrumproperty


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