K. Takimiya, Ken‐ichi Kato, Y. Aso
Aug 15, 2002
Citations
1
Influential Citations
16
Citations
Journal
ChemInform
Abstract
Two isomeric naphthodithiophenes (syn-NDT and anti-NDT), isoelectronic with pyrene, as well as their dimethyl, bis(methylthio), and di(2-thienyl) derivatives have been successfully synthesized as novel peri-fused heteroaromatics. Among them, the parent syn-NDT and the di(2-thienyl) derivative of anti-NDT were examined by X-ray crystallographic analyses, revealing that the molecular structures comprise fairly planar, but considerably strained skeletal rings, and their crystal structures are characterized by a herringbone arrangement of uniform stacking columns. The UV/vis spectra of these heteroaromatics show considerable red-shifts of the π–π* transitions as compared to that of pyrene, making them chromogens ranging from yellow to purple. Cyclic voltammetry indicates that they have much stronger electron donating abilities than pyrene. Consequently, all of them, except for the methyl derivatives, can form highly conductive molecular complexes with iodine and DDQ. In addition, the electrochemical oxidation...