Synthesis and Properties of New N-Heteroheptacenes for Solution-Based Organic Field Effect Transistors
Synthesis and Properties of New N-Heteroheptacenes for Solution-Based Organic Field Effect Transistors
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DOI：
10.1002/chem.201701966
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发表时间：
2017-09-12
影响因子：
4.3
通讯作者：
Driver, Tom
中科院分区：
文献类型：
--
作者：
Zhou, Fei;Liu, Sheng;Driver, Tom
通过Rh-2(II)催化的C-H键胺化反应，以邻噻吩基取代芳基叠氮化合物为原料合成了一系列N-杂七烯类化合物。该反应允许芳基叠氮上存在给电子基或脱电子基，而不会对胺化反应的产率产生不利影响。中心的噻吩环是由两个硫代吲哚片段通过钯催化的Stille反应来安装硫醚，然后再通过铜介导的Ullman反应来触发环化反应而生成的。得到的N-杂庚烯聚焦库的光物理和电化学性质表明，电子性质由芳烃取代基控制，而单晶生长表明堆积基序受N-取代基的影响。用N-杂庚烯制备了溶液处理的薄膜场效应管器件，其中一个表现出0.02 cm(2)V(-1)的空穴迁移率S(-1)。
A series of N-heteroheptacenes was synthesized from ortho-thiophene-substituted aryl azides using a Rh-2(II)-catalyzed C-H bond amination reaction to construct the thienoindole moieties. This reaction tolerated the presence of electron-donating or withdrawing groups on the aryl azide without adversely affecting the yield of the amination reaction. The central thiophene ring was created from two thienoindole pieces through a Pd-catalyzed Stille reaction to install the thioether followed by a Cu-mediated Ullman reaction to trigger the cyclization. The photophysical and electrochemical properties of the resulting focused library of N-heteroheptacenes revealed that the electronic nature is controlled by the arene substituent while single crystals grown reveal that the packing motif is influenced by the N-substituent. Solution-processed thin-film OFET devices were fabricated with the N-heteroheptacenes, and one exhibited a hole-mobility of 0.02cm(2)V(-1)s(-1).