Benzo[4,5]cyclohepta[1,2-b]fluorene: an isomeric motif for pentacene containing linearly fused five-, six- and seven-membered rings†,Chemical Science

当前位置： X-MOL 学术 › Chem. Sci. › 论文详情

Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)

Benzo[4,5]cyclohepta[1,2-b]fluorene: an isomeric motif for pentacene containing linearly fused five-, six- and seven-membered rings†
Chemical Science ( IF 7.6 ) Pub Date : 2016-06-07 00:00:00 , DOI: 10.1039/c6sc01795a
Xuejin Yang _{1,

2,

3,

4} , Xueliang Shi _{1,

5,

6} , Naoki Aratani _{7,

8,

9,

10} , Théo P. Gonçalves _{11,

12,

13,

14} , Kuo-Wei Huang _{11,

12,

13,

14} , Hiroko Yamada _{7,

8,

9,

10} , Chunyan Chi _{1,

5,

6} , Qian Miao _{1,

2,

3,

4}

Affiliation

Benzo[4,5]cyclohepta[1,2-b]fluorene (5a), a new π-conjugated polycyclic hydrocarbon containing linearly fused six-, five-, six-, seven- and six-membered rings (C₆–C₅–C₆–C₇–C₆), was designed and its stable derivatives 5b and 5c were synthesized. With 22 π electrons, 5a is an isomer of pentacene with quinoidal, dipolar ionic and diradical resonance forms. Molecules 5b and 5c were experimentally investigated with cyclic voltammetry, electronic absorption spectroscopy and X-ray crystallographic analysis, and theoretically studied by calculating the NICS value, diradical character and dipole moment. A comparison of 5a–c with pentacene and other pentacene analogues containing linearly fused five- or seven-membered rings was also conducted and discussed. It was found that 5b behaved as a p-type organic semiconductor in solution-processed thin film transistors with a field effect mobility of up to 0.025 cm² V⁻¹ s⁻¹.

中文翻译：

苯并[4,5]环庚[1,2- b ]芴：并五苯的异构体，其中包含线性稠合的五元，六元和七元环†

苯并[4,5]环庚[1,2- b ]芴（5a），一种新的π-共轭多环烃，含有线性稠合的六，五，六，七和六元环（C ₆ –C_设计了5 –C ₆ –C ₇ –C ₆），并合成了其稳定的导数5b和5c。具有22个π电子，5a是并五苯的异构体，具有喹啉，偶极离子和双自由基共振形式。分子5b和5c用循环伏安法，电子吸收光谱法和X射线晶体学分析法进行了实验研究，并通过计算NICS值，双自由基特性和偶极矩进行了理论研究。还进行了5a–c与并五苯和其他包含线性稠合五元或七元环的并五苯类似物的比较。发现5b在溶液处理的薄膜晶体管中表现为p型有机半导体，其场效应迁移率高达0.025cm ² V ^-1 s ^-1。

更新日期：2016-06-07

点击分享查看原文

点击收藏

公开下载

阅读更多本刊新发论文本刊介绍/投稿指南