Synthesis and Properties of Heterocyclic Acene Diimides

被引:51
作者
Li, Cheng [1 ,2 ]
Xiao, Chengyi [1 ,2 ]
Li, Yan [1 ]
Wang, Zhaohui [1 ]
机构
[1] Chinese Acad Sci, Inst Chem, Key Lab Organ Solids, Beijing Natl Lab Mol Sci, Beijing 100190, Peoples R China
[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China
基金
中国国家自然科学基金;
关键词
HIGH-PERFORMANCE; NAPHTHALENE DIIMIDE; PERYLENE BISIMIDES; N-CHANNEL; ORGANIC TRANSISTORS; TRIPHENODITHIAZINES; TETRACENE;
D O I
10.1021/ol303551p
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of heterocyclic acene diimides were synthesized effectively based on the condensation of o-phenylenediamine, 1,2-benzenedithiol, and 2-aminothiophenol with 2,3,6,7-tetrabromo-1,4,5,8-naphthalene tetracarboxylic diimide. The diimides exhibit interesting optical and electrical properties with one of them showing a hole mobility up to 0.02 cm(2) V-1 s(-1).
引用
收藏
页码:682 / 685
页数:4
相关论文
共 44 条
[1]   LADDER OLIGOPHENOTHIAZINES BY DIRECT THIONATION OF N-ARYLANILINO DERIVATIVES [J].
ANDREANI, F ;
BIZZARRI, PC ;
DELLACASA, C ;
FIORINI, M ;
SALATELLI, E .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1991, 28 (02) :295-299
[2]   An efficient synthesis of quaterrylenedicarboximide NIR dyes [J].
Avlasevich, Yuri ;
Muellen, Klaus .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (26) :10243-10246
[3]   Synthesis and applications of core-enlarged perylene dyes [J].
Avlasevich, Yuri ;
Li, Chen ;
Muellen, Klaus .
JOURNAL OF MATERIALS CHEMISTRY, 2010, 20 (19) :3814-3826
[4]   Supramolecular construction of vesicles based on core-substituted naphthalene diimide appended with triethyleneglycol motifs [J].
Bhosale, Sheshanath V. ;
Jani, Chintan H. ;
Lalander, Cecilia H. ;
Langford, Steven J. ;
Nerush, Igor ;
Shapter, Joseph G. ;
Villamaina, Diego ;
Vauthey, Eric .
CHEMICAL COMMUNICATIONS, 2011, 47 (29) :8226-8228
[5]   Solvophobic control of core-substituted naphthalene diimide nanostructures [J].
Bhosale, Sheshanath V. ;
Jani, Chintan ;
Lalander, Cecilia H. ;
Langford, Steven J. .
CHEMICAL COMMUNICATIONS, 2010, 46 (06) :973-975
[6]   Regiocontrolled formation of a novel dioxadithiapentacene [J].
Boros, EE ;
Harfenist, M .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (26) :10045-10047
[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]   RECENT ADVANCES IN NONLINEAR SPECTROSCOPY AND NONLINEAR OPTICAL-MATERIALS [J].
DALTON, LR ;
SAPOCHAK, LS ;
YU, LP .
JOURNAL OF PHYSICAL CHEMISTRY, 1993, 97 (12) :2871-2883
[9]   1,6-disubstituted perylene bisimides: concise synthesis and characterization as near-infrared fluorescent dyes [J].
Fan, LQ ;
Xu, YP ;
Tian, H .
TETRAHEDRON LETTERS, 2005, 46 (26) :4443-4447
[10]   First synthesis of 2,3,6,7-tetrabromonaphthalene diimide [J].
Gao, Xike ;
Qiu, Wenfeng ;
Yang, Xiaodi ;
Liu, Yunqi ;
Wang, Ying ;
Zhang, Hengjun ;
Qi, Ting ;
Liu, Ying ;
Lu, Kun ;
Du, Chunyan ;
Shuai, Zhigang ;
Yu, Gui ;
Zhu, Daoben .
ORGANIC LETTERS, 2007, 9 (20) :3917-3920