Synthesis, structure, and properties of benzoquinone dimer and trimers bearing t-Bu substituents.
Highly soluble and stable quinone dimer and trimers were successfully yielded by introduction of t-Bu substituents. In X-ray structure analysis, the dimer quinone moiety was distorted into the boat shape, which was clarified by MO calculations. X-ray and UV/vis studies indicated that the covalently linked quinone moieties bear a large torsional angle. Nevertheless, the reduction potentials rose significantly with the order of monomer < dimer < trimer, indicating that the negative charge was efficiently delocalized within the radical anions.
Hayashi
Naoto
N
Graduate School of Science and Engineering, University of Toyama, Gofuku, Toyama 9308555, Japan.
Yoshikawa
Takahiro
T
Ohnuma
Takahiro
T
Higuchi
Hiroyuki
H
Sako
Katsuya
K
Uekusa
Hidehiro
H
D016227:Benzoquinones / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D011108:Polymers / Q000737:chemistry*; D013056:Spectrophotometry, Ultraviolet; D014961:X-Ray Diffraction
D016227:Benzoquinones; D011108:Polymers