Further insight into aryl nitration of tetraphenylporphyrin

Zhi Xue, Priscilla P.S. Lee, Yanming Wang, Daniel W J KWONG, Jing Li, John H. Xin, Rick W K WONG*, Kevin K.L. Cheuk

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)

Abstract

We report an in-depth study on meso-aryl nitration of tetraphenylporphyrin. In contrast to previous studies, new evidence reveals that tetrakis(p- nitrophenyl) derivative can be obtained as a major product. Successful isolation of the barely soluble product toward a remarkable yield of nearly 90% has been reached by means of a solid phase extraction technique. Distribution of different nitro-porphyrin components is reassessed with respect to varying acid content in the reactions. An ortho-effect model is proposed to describe the formation mechanism.

Original languageEnglish
Pages (from-to)6030-6035
Number of pages6
JournalTetrahedron
Volume67
Issue number33
DOIs
Publication statusPublished - 19 Aug 2011

Scopus Subject Areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

User-Defined Keywords

  • 5,10,15,20-Tetrakis(4-nitrophenyl)-21H,23H-porphyrin
  • Nitration
  • Porphyrin functionalization
  • Porphyrin synthesis
  • Tetra-meso-phenylporphyrin

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