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Difluoroboron Chelation to Quinacridonequinone: A Synthetic Method for Air‐Sensitive 6,13‐Dihydroxyquinacridone via Boron Complexes
Author(s) -
Moriya Koichiro,
Shimada Ryohei,
Ono Katsuhiko
Publication year - 2019
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201900219
Subject(s) - chelation , reagent , chemistry , hydrolysis , denticity , boron , nuclear chemistry , inorganic chemistry , crystal structure , crystallography , organic chemistry
This study aims to perform the chelation of difluoroboron (BF 2 ) to quinacridonequinone (QQ). The resulting dark green solid was determined to be QA‐BF 2 , which is a BF 2 complex of 6,13‐dihydroxyquinacridone (QA‐OH), and not QQ‐BF 2 , which is a BF 2 complex of QQ. This result indicated that QQ‐BF 2 was first generated as an O , O ‐bidentate chelate, which immediately underwent a two‐electron reduction to produce QA‐BF 2 . 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 BF 2 chelation and hydrolysis was proposed. QA‐BF 2 and QA‐OH are useful organic functional pigments and reducing reagents.