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- Title
Difluoroboron Chelation to Quinacridonequinone: A Synthetic Method for Air‐Sensitive 6,13‐Dihydroxyquinacridone via Boron Complexes.
- Authors
Moriya, Koichiro; Shimada, Ryohei; Ono, Katsuhiko
- Abstract
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.
- Subjects
BORON; HOLE mobility; CHELATION; HYDROLYSIS; PIGMENTS
- Publication
Chemistry - An Asian Journal, 2019, Vol 14, Issue 9, p1452
- ISSN
1861-4728
- Publication type
Article
- DOI
10.1002/asia.201900219