Synthesis of 9-chloro-1,10-anthraquinone and its reactions with amines

Abstract

l-Dichlorophosphoryloxy-9,9-dichloroanthrone, a product of the reaction between I-hydroxyanthraquinone and PCI 5, reacts with primary amines in benzene to give first l-(diaminophosphoryloxy)-9,9-dichloroanthrones and then the corresponding 9-imines. The reaction in DMF occurs with elimination of the phosphoryloxy group and generation of 9-chloro-l,10-anthraquinone that undergoes amination followed by substitution of the hydrogen atom in position 4 rather than a chlorine atom in position 9, which is the most active position in 2,4,9-trichtoro-1,10-anthraquinone. The second step of amination results in 4,9-di(alkylamino)-l,10-anthraquinone. The literature data on obtaining individual 9-chloro-l,10-anthraquinone under the action of bases on l-dichorophosphoryloxy-9,9-dichloroanthrone were not experimentally supported.

Optical and Electrochemical Properties of Anthraquinone Imine Based Dyes for Dye‐Sensitized Solar Cells

“…The photostability of 9,10-anthraquinone derivatives, their historical background, and their optical properties prompted us to study the condensation reactions of 1-hydroxy-9,10-anthraquinone derivatives with primary aromatic amines to form the previously reported anthraquinone imine 1, [11] the new anthraquinone imines 2 and 3, and the anthrone diamine 4 (Figure 2), which by no means is a straightforward selective reaction. [12][13][14] Our aim was to synthesize molecular dyes with a six-membered chelate ring ligand cavity as an anchor for interaction with Lewis acidic metal ions, which would easily replace a proton in these chelates.…”