Convenient synthesis of tridentate 2,6-di(pyrazol-1-yl)-4-carboxypyridine and tetradentate 6,6′-di(pyrazol-1-yl)-4,4′-dicarboxy-2,2′- bipyridine ligands

Cédric Klein, Etienne Baranoff, Michael Grätzel, Md Khaja Nazeeruddin, Etienne Baranoff

Research output: Contribution to journalArticlepeer-review

21 Citations (Scopus)

Abstract

Citrazinic acid is used as a convenient starting material for both tridentate 2,6-di(pyrazol-1-yl)-pyridine and tetradentate 6,6′-di(pyrazol- 1-yl)-2,2′-bipyridine ligands containing carboxylic groups useful for further anchoring of sensitizer on TiO2 for dye-sensitized solar cells (DSCs). Using 2,6-dichloro-4-carboxypyridine, the synthesis of the terdentate ligands was improved compared to previously used 2,6-dibromo-4- carboxypyridine or 2,6-dichloro-4-ethylcarboxylate pyridine. Controlling the reaction conditions, it is possible to efficiently obtain the monosubstituted 2-chloro-6-pyrazol-1-yl-4-carboxypyridine, a key intermediate for the preparation of tetradentate 6,6′-di(pyrazol-1-yl)-4,4′-dicarboxy-2, 2′-bipyridine ligand.

Original languageEnglish
Pages (from-to)584-587
Number of pages4
JournalTetrahedron Letters
Volume52
Issue number5
DOIs
Publication statusPublished - 2 Feb 2011

Keywords

  • Bipyridine
  • Dye-sensitized solar cells
  • Pyrazole
  • Terdentate ligands
  • Tetradentate ligands

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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