Synthesis and Characterization of Amino Acid Bridged Novel Chiral Zinc Porphyrin Dimer

Chem. J. Chinese Universities ›› 1998, Vol. 19 ›› Issue (4): 511.

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Synthesis and Characterization of Amino Acid Bridged Novel Chiral Zinc Porphyrin Dimer

LIU Hai-Yang², HUANG Jin-Wang¹, TIAN Xuan³, HU Xin-Ming², JI Liang-Nian¹

1. Department of Chemistry, Zhongshan University, Guangzhou, 510275;
2. Department of Applied Chmistry, South China University of Technology, Guangzhou, 510641;
3. National Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, 730000

Received:1997-11-24 Online:1998-04-24 Published:1998-04-24

Abstract

Abstract: Novel phenylalanine bridged dimeric porphyrin was synthesized by the reaction of 5-[o-(2-bromo-1-ethoxyl)]-10,15,20-triphenylporphyrin and amino acid in DMF in the presence of phase transfer catalyst BTEACin about 10%—15% yields. Zinc complexes derived exhibit strong split induced circular dichroism(ICD) at the soret absorption region and weak single peak ICD at the Qabsorption. While the corresponding free base porphyrin exhibits no obvious ICD. L-and D-phenylalanine bridged zinc porphyrin dimer constituted pairs of enantiomers. These complexes can be used as good model compounds for the investigation of induced circular dichroism of porphyrin occurring in natural systems.

Key words: Amino acid, Chiral porphyrin dimer, Synthesis

CLC Number:

O627.23

TrendMD:

LIU Hai-Yang, HUANG Jin-Wang, TIAN Xuan, HU Xin-Ming, JI Liang-Nian . Synthesis and Characterization of Amino Acid Bridged Novel Chiral Zinc Porphyrin Dimer[J]. Chem. J. Chinese Universities, 1998, 19(4): 511.

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Synthesis and Characterization of Amino Acid Bridged Novel Chiral Zinc Porphyrin Dimer

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