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Research on Chemical Intermediates

, Volume 40, Issue 4, pp 1415–1423 | Cite as

Studies on selective β/β′ bromination of π-extended porphyrins and subsequent coupling reactions

  • Jiaying Yan
  • Yaqing Feng
  • Nuonuo Zhang
  • Bao Zhang
Article

Abstract

Monobromination of β, β-π-extended porphyrins was found to selectively occur at the β or β position of the porphyrins which is antipodal to the fused aromatic ring. Subsequent Sonogashira or Heck coupling of the resultant bromoporphyrin introduced a carboxylphenylethynyl group or an acrylic acid group to the π-extended porphyrin. The optimal reaction conditions were found for the Sonogashira and Heck coupling reaction. All of the coupling products have shown a broadening and red-shift of the Soret band and Q bands in the UV–Vis absorption spectra compared with the π-extended porphyrin starting materials and the original unmodified porphyrins.

Keywords

Large π-aromatic Porphyrin Bromination Selectivity Sonogashira Heck 

Notes

Acknowledgments

This work is supported by National Natural Science Foundation of China (No. 21076147), Natural Science Foundation of Tianjin (No. 10JCZDJC23700), China International Science and Technology Project (No 2012DFG41980) and Seed Foundation of Tianjin University (Bao Zhang).

Supplementary material

11164_2013_1048_MOESM1_ESM.docx (14 kb)
Supplementary material 1 (DOCX 13 kb)

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Copyright information

© Springer Science+Business Media Dordrecht 2013

Authors and Affiliations

  • Jiaying Yan
    • 1
  • Yaqing Feng
    • 1
  • Nuonuo Zhang
    • 1
  • Bao Zhang
    • 1
  1. 1.School of Chemical Engineering and TechnologyTianjin UniversityTianjinChina

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