Facile Synthesis of 3-(Azol-1-yl)-1-adamantanecarboxylic Acids—New Bifunctional Angle-Shaped Building Blocks for Coordination Polymers

Dmitry Pavlov, Taisiya Sukhikh, Evgeny Filatov, Andrei Potapov

Research output: Contribution to journalArticle

Abstract

For the first time, orthogonally substituted azole-carboxylate adamantane ligands were synthesized and used for preparation of coordination polymers. The angle-shaped ligands were prepared by the reaction of 1-adamantanecarboxylic acid and azoles (1H-1,2,4-triazole, 3-methyl-1H-1,2,4-triazole, 3,5-dimethyl-1H-1,2,4-triazole, 1H-tetrazole, 5-methyl-1H-tetrazole) in concentrated sulfuric acid. Variation of the solvent and substituents in azole rings allowed to prepare both 1D and 2D copper(II) and nickel(II) coordination polymers, [Cu2(trzadc)4(H2O)0.7]·DMF·0.3H2O, [Cu(trzadc)2(MeOH)]·MeOH, [Ni(trzadc)2(MeOH)2] and [Cu2(mtrzadc)3(MeOH)]+NO3 (trzadc-3-(1,2,4-triazol-1-yl)-adamantane-1-carboxylic acid; mtrzadc-3-(3-methyl-1,2,4-triazol-1-yl)-adamantane-1-carboxylic acid) which were structurally characterized by single crystal X-ray diffraction. Complex [Cu(trzadc)2(MeOH)]·MeOH was shown to act as a catalyst in the Chan-Evans-Lam arylation reaction.

Original languageEnglish
Article number2717
JournalMolecules
Volume24
Issue number15
DOIs
Publication statusPublished - 26 Jul 2019

Fingerprint

Adamantane
azoles
Danazol
Azoles
coordination polymers
tetrazoles
Polymers
Carboxylic Acids
carboxylic acids
synthesis
Ligands
ligands
sulfuric acid
Nickel
X-Ray Diffraction
carboxylates
Copper
Single crystals
nickel
catalysts

Keywords

  • Adamantane
  • Carboxylate ligands
  • Chain structures
  • Heterocyclic ligands
  • Metal-organic frameworks

ASJC Scopus subject areas

  • Analytical Chemistry
  • Chemistry (miscellaneous)
  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Facile Synthesis of 3-(Azol-1-yl)-1-adamantanecarboxylic Acids—New Bifunctional Angle-Shaped Building Blocks for Coordination Polymers. / Pavlov, Dmitry; Sukhikh, Taisiya; Filatov, Evgeny; Potapov, Andrei.

In: Molecules, Vol. 24, No. 15, 2717, 26.07.2019.

Research output: Contribution to journalArticle

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abstract = "For the first time, orthogonally substituted azole-carboxylate adamantane ligands were synthesized and used for preparation of coordination polymers. The angle-shaped ligands were prepared by the reaction of 1-adamantanecarboxylic acid and azoles (1H-1,2,4-triazole, 3-methyl-1H-1,2,4-triazole, 3,5-dimethyl-1H-1,2,4-triazole, 1H-tetrazole, 5-methyl-1H-tetrazole) in concentrated sulfuric acid. Variation of the solvent and substituents in azole rings allowed to prepare both 1D and 2D copper(II) and nickel(II) coordination polymers, [Cu2(trzadc)4(H2O)0.7]·DMF·0.3H2O, [Cu(trzadc)2(MeOH)]·MeOH, [Ni(trzadc)2(MeOH)2] and [Cu2(mtrzadc)3(MeOH)]+NO3 – (trzadc-3-(1,2,4-triazol-1-yl)-adamantane-1-carboxylic acid; mtrzadc-3-(3-methyl-1,2,4-triazol-1-yl)-adamantane-1-carboxylic acid) which were structurally characterized by single crystal X-ray diffraction. Complex [Cu(trzadc)2(MeOH)]·MeOH was shown to act as a catalyst in the Chan-Evans-Lam arylation reaction.",
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