6,13-二氨基取代并五苯的合成与表征

Synthesis and Characterization of 6,13-Diamino-Substituted Pentacenes.

作者信息

Ito Akihiro, Uebe Masashi, Takahashi Kazuki, Ishikawa Hiroshi, Sakamaki Daisuke, Sato Hiroyasu, Matsumoto Takashi, Tanaka Kazuyoshi

机构信息

Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto, 615-8510, Japan.

X-ray Research Laboratory, Rigaku Corporation, Matsubara-cho 3-9-12, Akishima, Tokyo, 196-8666, Japan.

出版信息

Chemistry. 2016 Feb;22(6):2165-2170. doi: 10.1002/chem.201503996. Epub 2016 Jan 8.

DOI:10.1002/chem.201503996

PMID:26748609

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.

摘要

已制备出一系列6,13 - 二氨基取代并五苯1 a - d，并将其表征为一类新型的并五苯衍生物，具有强给电子能力且在常见有机溶剂中的溶解性增强。光谱电化学和密度泛函理论研究表明，双电子氧化过程伴随着并五苯部分显著的结构变化，转变为蝴蝶状构象。更重要的是，通过改变N - 取代基，可以调节6,13 - 二氨基并五苯双阳离子中平面并五苯部分的变形程度。