- Difluoroboron Chelation to Quinacridonequinone: A Synthetic Method for Air-Sensitive 6,13-Dihydroxyquinacridone via Boron Complexes
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This study aims to perform the chelation of difluoroboron (BF2) to quinacridonequinone (QQ). The resulting dark green solid was determined to be QA-BF2, which is a BF2 complex of 6,13-dihydroxyquinacridone (QA-OH), and not QQ-BF2, which is a BF2 complex of QQ. This result indicated that QQ-BF2 was first generated as an O,O-bidentate chelate, which immediately underwent a two-electron reduction to produce QA-BF2. This compound was converted to air-sensitive QA-OH by undergoing hydrolysis in argon. Since QA-OH has a strong electron-donating property, it easily produced QQ via air oxidation in the solution. QA-OH also acts as a reducing reagent for quinones. The crystal packing of QA-OH is a herringbone type with short π???π contacts, and a good hole mobility has been suggested by theoretical calculations. Herein, a new synthetic method from QQ to QA-OH using BF2 chelation and hydrolysis was proposed. QA-BF2 and QA-OH are useful organic functional pigments and reducing reagents.
- Moriya, Koichiro,Shimada, Ryohei,Ono, Katsuhiko
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- PREPARATION OF QUINACRIDONEQUINONES AND SUBSTITUTED DERIVATIVES OF SAME
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A process for by oxidizing a quinacridone in a liquid medium with a non-metal oxidant producing a quinacridonequinone.
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(2008/06/13)
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