Large π-Conjugated Quinacridone Derivatives: Syntheses, Characterizations, Emission, and Charge Transport Properties

被引：24

作者：

Chen, Weiping ^{[1
]}

Tian, Kui ^{[2
]}

Song, Xiaoxian ^{[1
]}

Zhang, Zuolun ^{[1
]}

Ye, Kaiqi ^{[1
]}

Yu, Gui ^{[2
]}

Wang, Yue ^{[1
]}

机构：

[1] Jilin Univ, Coll Chem, State Key Lab Supramol Struct & Mat, Changchun 130012, Peoples R China

[2] Chinese Acad Sci, Beijing Natl Lab Mol Sci, Inst Chem, Beijing 100190, Peoples R China

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 24期

基金：

中国国家自然科学基金;

关键词：

HIGH-PERFORMANCE; ORGANIC SEMICONDUCTORS; POLYMERS; DIKETOPYRROLOPYRROLE; ACCEPTOR; DIIMIDE;

D O I：

10.1021/acs.orglett.5b03155

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two 11-ring-fused quinacridone derivatives, TTQA and DCNTTQA, have been synthesized by ferric chloride mediated cyclization and Knoevenagel reaction. Replacement of the carbonyl groups (in TTQA) with dicyanoethylene groups (in DCNTTQA) not only red-shifted the emission to the near-infrared region but also led to a nonplanar skeleton that significantly improved the solubility of DCNTTQA. Moreover, dicyanoethylene groups rendered DCNTTQA low-lying HOMO and LUMO levels. DCNTTQA-based solution-processed field-effect transistors showed a hole mobility up to 0.217 cm(2) V-1 s(-1).

引用

页码：6146 / 6149

页数：4

共 49 条

[41] One-Pot Synthesis of Brightly Fluorescent Mes2B-Functionalized Indolizine Derivatives via Cycloaddition Reactions [J].

Yang, Deng-Tao ;

Radtke, Julian ;

Mellerup, Soren K. ;

Yuan, Kang ;

Wang, Xiang ;

Wagner, Matthias ;

Wang, Suning .

ORGANIC LETTERS, 2015, 17 (10) :2486-2489

[42] Supramolecular structures and assembly and luminescent properties of quinacridone derivatives [J].

Ye, KQ ;

Wang, J ;

Sun, H ;

Liu, Y ;

Mu, ZC ;

Li, F ;

Jiang, SM ;

Zhang, JY ;

Zhang, HX ;

Wang, Y ;

Che, CM .

JOURNAL OF PHYSICAL CHEMISTRY B, 2005, 109 (16) :8008-8016

[43] Recent Highlights and Perspectives on Acene Based Molecules and Materials [J].

Ye, Qun ;

Chi, Chunyan .

CHEMISTRY OF MATERIALS, 2014, 26 (14) :4046-4056

[44] Incorporating TCNQ into Thiophene-Fused Heptacene for n-Channel Field Effect Transistor [J].

Ye, Qun ;

Chang, Jingjing ;

Huang, Kuo-Wei ;

Dai, Gaole ;

Zhang, Jie ;

Chen, Zhi-Kuan ;

Wu, Jishan ;

Chi, Chunyan .

ORGANIC LETTERS, 2012, 14 (11) :2786-2789

[45] Thiophene-Fused Tetracene Diimide with Low Band Gap and Ambipolar Behavior [J].

Ye, Qun ;

Chang, Jingjing ;

Huang, Kuo-Wei ;

Chi, Chunyan .

ORGANIC LETTERS, 2011, 13 (22) :5960-5963

[46] Synthesis and Properties of a New Class of Fully Conjugated Azahexacene Analogues [J].

Yue, Wan ;

Suraru, Sabin-Lucian ;

Bialas, David ;

Mueller, Matthias ;

Wuerthner, Frank .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (24) :6159-6162

[47] Cyano- and chloro-substituted coronene diimides as solution-processable electron-transporting semiconductors [J].

Zhang, Chenhao ;

Shi, Ke ;

Cai, Kang ;

Xie, Jiajun ;

Lei, Ting ;

Yan, Qifan ;

Wang, Jie-Yu ;

Pei, Jian ;

Zhao, Dahui .

CHEMICAL COMMUNICATIONS, 2015, 51 (33) :7144-7147

[48] Novel Butterfly-Shaped Fused Heteroacenes: Synthesis, Properties, and Device Performance of Solution-Processed Field-Effect Transistors [J].

Zhang, Weifeng ;

Sun, Xiangnan ;

Xia, Pingfang ;

Huang, Jianyao ;

Yu, Gui ;

Wong, Man Shing ;

Liu, Yunqi ;

Zhu, Daoben .

ORGANIC LETTERS, 2012, 14 (17) :4382-4385

[49] Nitrile-Substituted QA Derivatives: New Acceptor Materials for Solution-Processable Organic Bulk Heterojunction Solar Cells [J].

Zhou, Tianlei ;

Jia, Tao ;

Kang, Bonan ;

Li, Fenghong ;

Fahlman, Mats ;

Wang, Yue .

ADVANCED ENERGY MATERIALS, 2011, 1 (03) :431-439

← 1 2 3 4 5 →