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Synthesis and Characterization of 6,13‐Diamino‐Substituted Pentacenes
Authors:Dr Akihiro Ito  Masashi Uebe  Kazuki Takahashi  Hiroshi Ishikawa  Dr Daisuke Sakamaki  Dr Hiroyasu Sato  Dr Takashi Matsumoto  Prof?Dr Kazuyoshi Tanaka
Institution:1. Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto, Japan;2. X-ray Research Laboratory, Rigaku Corporation, Akishima, Tokyo, Japan
Abstract:A series of 6,13‐diamino‐substituted pentacenes 1 a – d has been prepared and characterized as a new class of pentacene derivatives with strong donor ability and enhanced solubility in common organic solvents. The spectroelectrochemical and DFT studies revealed that the two‐electron oxidation process was accompanied by the substantial structural change into a butterfly‐like conformation of the pentacene moiety. More importantly, the extent of deformation from the planar pentacene moiety in the dications of 6,13‐diaminopentacene is tunable by varying the N‐substituents.
Keywords:density functional calculations  electrochemistry  pi interactions  UV/Vis spectroscopy
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