6,13-双（烷硫基）并五苯的合成及共面π-堆积排列

Synthesis and cofacial pi-stacked packing arrangement of 6,13-bis(alkylthio)pentacene.

作者信息

Kobayashi Kenji, Shimaoka Reishi, Kawahata Masatoshi, Yamanaka Masamichi, Yamaguchi Kentaro

机构信息

Department of Chemistry, Faculty of Science, Shizuoka University, Suruga-ku, Japan.

出版信息

Org Lett. 2006 May 25;8(11):2385-8. doi: 10.1021/ol060679x.

DOI:10.1021/ol060679x

PMID:16706532

Abstract

[reaction: see text] 6,13-Bis(alkylthio)pentacenes directed toward organic field-effect transistors (OFETs) were synthesized by the ZnI(2)-mediated reaction of trans-6,13-dihydroxy-6,13-dihydropentacene with alkylthiols, followed by the dehydrogenative aromatization of the resulting trans-6,13-bis(alkylthio)-6,13-dihydropentacenes with p-chloranil. The X-ray crystallographic analysis of 6,13-bis(methylthio)pentacene reveals that this compound is arranged as a result of cofacial pi-stacking with S-S and S-pi interactions.

摘要

[反应：见正文] 用于有机场效应晶体管（OFET）的6,13-双（烷硫基）并五苯是通过反式-6,13-二羟基-6,13-二氢并五苯与烷硫醇在ZnI₂介导下反应，然后将所得的反式-6,13-双（烷硫基）-6,13-二氢并五苯与四氯对苯醌进行脱氢芳构化反应合成的。6,13-双（甲硫基）并五苯的X射线晶体学分析表明，该化合物是通过S-S和S-π相互作用的共面π堆积排列而成。