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

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 (1<i>H</i>-1,2,4-triazole, 3-methyl-1<...

Full description

Bibliographic Details
Published in:Molecules
Main Authors: Dmitry Pavlov, Taisiya Sukhikh, Evgeny Filatov, Andrei Potapov
Format: Article
Language:English
Published: MDPI AG 2019-07-01
Subjects:
adamantane
carboxylate ligands
chain structures
heterocyclic ligands
metal-organic frameworks
Online Access:https://www.mdpi.com/1420-3049/24/15/2717
Description
Summary: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 (1<i>H</i>-1,2,4-triazole, 3-methyl-1<i>H</i>-1,2,4-triazole, 3,5-dimethyl-1<i>H</i>-1,2,4-triazole, 1<i>H</i>-tetrazole, 5-methyl-1<i>H</i>-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, [Cu<sub>2</sub>(trzadc)<sub>4</sub>(H<sub>2</sub>O)<sub>0.7</sub>]∙DMF∙0.3H<sub>2</sub>O, [Cu(trzadc)<sub>2</sub>(MeOH)]∙MeOH, [Ni(trzadc)<sub>2</sub>(MeOH)<sub>2</sub>] and [Cu<sub>2</sub>(mtrzadc)<sub>3</sub>(MeOH)]<sup>+</sup>NO<sub>3</sub><sup>&#8722;</sup> (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)<sub>2</sub>(MeOH)]∙MeOH was shown to act as a catalyst in the Chan-Evans-Lam arylation reaction.
ISSN:1420-3049

Similar Items