Synthesis and characterization of 2,7-bis(2-pyridyl)-1,8-diazaanthraquinone — A redox-active ligand designed for the construction of supramolecular grids

Author:

Jain Rajsapan,Caldwell Sharon L,Louie Anika S,Hicks Robin G

Abstract

Double condensation of 2-acetylpyridine with 1,3-diaminobenzene-4,6-dicarboxaldehyde affords 2,7-bis(2-pyridyl)-1,8-diazaanthracene, which was subsequently oxidized to the corresponding quinone. Electrochemical studies indicate two reversible reduction processes corresponding to semiquinone and hydroquinonate formation. Electron-withdrawing pyridine groups and the nitrogen atoms make this somewhat more easily reduced than anthraquinone. This compound is redox-active and can be reduced to its radical anion, a potential spin-bearing ligand for the construction of [2 × 2] metallo-grid structures.Key words: quinone, grid, supramolecular, bistridentate, electrochemistry, metallosupramolecular chemistry.

Publisher

Canadian Science Publishing

Subject

Organic Chemistry,General Chemistry,Catalysis

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