Cyanated Diazatetracene Diimides with Ultrahigh Electron Affinity for n-Channel Field Effect Transistors

被引：72

作者：

Ye, Qun ^{[1
]}

Chang, Jingjing ^{[1
]}

Huang, Kuo-Wei ^{[2
,3
]}

Shi, Xueliang ^{[1
]}

Wu, Jishan ^{[1
,4
]}

Chi, Chunyan ^{[1
]}

机构：

[1] Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore

[2] King Abdullah Univ Sci & Technol KAUST, Div Phys Sci & Engn, Thuwal 239556900, Saudi Arabia

[3] KAUST Catalysis Ctr, Thuwal 239556900, Saudi Arabia

[4] ASTAR, Inst Mat Res & Engn, Singapore 117602, Singapore

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 06期

关键词：

NAPHTHALENE DIIMIDES; SEMICONDUCTORS; BISIMIDES; TETRACENE; DESIGN;

D O I：

10.1021/ol400082c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Several diazatetracene diimides with high electron affinity (up to 4.66 eV!) were prepared and well characterized. The LUMO energy level of these electron-deficient molecules was found to be closely related to their material stability. Compound 7 with ultrahigh electron affinity suffered from reduction and hydrolysis in the presence of silica gel or water. The stable compounds 3 and 6 showed n-channel FET behavior with an average electron mobility of 0.002 and 0.005 cm(2) V-1 s(-1), respectively, using a solution processing method.

引用

页码：1194 / 1197

页数：4

共 44 条

[1] Cyanated perylene-3,4-dicarboximides and perylene-3,4:9,10-bis(dicarboximide):: Facile chromophoric oxidants for organic photonics and electronics [J].

Ahrens, MJ ;

Fuller, MJ ;

Wasielewski, MR .

CHEMISTRY OF MATERIALS, 2003, 15 (14) :2684-2686

[2] Effects of electronegative substitution on the optical and electronic properties of acenes and diazaacenes [J].

Appleton, Anthony Lucas ;

Brombosz, Scott M. ;

Barlow, Stephen ;

Sears, John S. ;

Bredas, Jean-Luc ;

Marder, Seth R. ;

Bunz, Uwe H. F. .

NATURE COMMUNICATIONS, 2010, 1

[3] Chemistry of naphthalene diimides [J].

Bhosale, Sheshanath V. ;

Jani, Chintan H. ;

Langford, Steven J. .

CHEMICAL SOCIETY REVIEWS, 2008, 37 (02) :331-342

[4] RETRACTED: A Core-Substituted Naphthalene Diimide Fluoride Sensor (Retracted Article) [J].

Bhosale, Sheshanath V. ;

Bhosale, Sidhanath V. ;

Kalyankar, Mohan B. ;

Langford, Steven J. .

ORGANIC LETTERS, 2009, 11 (23) :5418-5421

[5] The larger N-heteroacenes [J].

Bunz, Uwe H. F. .

PURE AND APPLIED CHEMISTRY, 2010, 82 (04) :953-968

[6] N-Heteroacenes [J].

Bunz, Uwe H. F. .

CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (28) :6780-6789

[7] Large hydroazaacene diimides: synthesis, tautomerism, halochromism, and redox-switchable NIR optics [J].

Cai, Kang ;

Yan, Qifan ;

Zhao, Dahui .

CHEMICAL SCIENCE, 2012, 3 (11) :3175-3182

[8] 6,13-Dicyano pentacene-2,3:9,10-bis(dicarboximide) for solution-processed air-stable n-channel field effect transistors and complementary circuit [J].

Chang, Jingjing ;

Qu, Hemi ;

Ooi, Zi-En ;

Zhang, Jie ;

Chen, Zhikuan ;

Wu, Jishan ;

Chi, Chunyan .

JOURNAL OF MATERIALS CHEMISTRY C, 2013, 1 (03) :456-462

[9] Stepwise Cyanation of Naphthalene Diimide for n-Channel Field-Effect Transistors [J].

Chang, Jingjing ;

Ye, Qun ;

Huang, Kuo-Wei ;

Zhang, Jie ;

Chen, Zhi-Kuan ;

Wu, Jishan ;

Chi, Chunyan .

ORGANIC LETTERS, 2012, 14 (12) :2964-2967

[10] Syntheses and properties of core-substituted naphthalene bisimides with aryl ethynyl or cyano groups [J].

Chopin, Stephanie ;

Chaignon, Frederique ;

Blart, Errol ;

Odobel, Fabrice .

JOURNAL OF MATERIALS CHEMISTRY, 2007, 17 (39) :4139-4146

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