Novel Ladder π-Conjugated Materials-Sila-Pentathienoacenes: Synthesis, Structure, and Electronic Properties

被引:16
作者
Wan, Jun-Hua [1 ]
Fang, Wei-Fen [1 ]
Li, Zhi-Fang [1 ]
Xiao, Xu-Qiong [1 ]
Xu, Zheng [1 ]
Deng, Yuan [1 ]
Zhang, Li-Hong [1 ]
Jiang, Jian-Xiong [1 ]
Qiu, Hua-Yu [1 ]
Wu, Lian-Bin [1 ]
Lai, Guo-Qiao [1 ]
机构
[1] Hangzhou Normal Univ, Key Lab Organosilicon Chem & Mat Technol, Minist Educ, Hangzhou 310012, Zhejiang, Peoples R China
基金
中国国家自然科学基金; 国家高技术研究发展计划(863计划);
关键词
conjugation; ladder compounds; polycycles; semiconductors; silicon; STACKED ORGANIC SEMICONDUCTOR; FIELD-EFFECT TRANSISTORS; THIN-FILM TRANSISTORS; ALKYL CHAIN-LENGTH; HIGH-PERFORMANCE; PHOTOPHYSICAL PROPERTIES; PHOTOVOLTAIC PROPERTIES; OPTICAL-PROPERTIES; HIGH-MOBILITY; DERIVATIVES;
D O I
10.1002/asia.201000287
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A novel series of ladder pi-conjugated materials-sila-pentathienoacenes (Si-PTA) are synthesized and characterized. Crystal structures of the compounds show that the length of alkyl chains substituting on the thiophene ring has a significant influence on molecular packing. A densely packed structure with an interfacial distance of about 3.66 angstrom between the adjacent molecules is observed for the compound with shorter alkyl chains. However, a large interfacial distance (7.99 angstrom) is obtained for another compound because of the insertion of long alkyl chains between two planes. The investigation of the optical and electrochemical properties shows that the silylene bridge incorporated into the pentathienoacene framework exerts a clear effect on the electronic properties by the sigma*-pi* conjugation. Although only a slight enhancement is observed for the HOMO levels, with respect to that of pentathienoacene, the LUMO levels are significantly lowered. The observed electronic properties are consistent with the theoretical calculations.
引用
收藏
页码:2290 / 2296
页数:7
相关论文
共 87 条
[41]   Highly fluorescent solid-state asymmetric spirosilabifluorene derivatives [J].
Lee, SH ;
Jang, BB ;
Kafafi, ZH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (25) :9071-9078
[42]   High-efficiency solution processable polymer photovoltaic cells by self-organization of polymer blends [J].
Li, G ;
Shrotriya, V ;
Huang, JS ;
Yao, Y ;
Moriarty, T ;
Emery, K ;
Yang, Y .
NATURE MATERIALS, 2005, 4 (11) :864-868
[43]   Synthesis of novel ladder bis-silicon-bridged p-terphenyls [J].
Li, Liangchun ;
Xiang, Junfeng ;
Xu, Caihong .
ORGANIC LETTERS, 2007, 9 (23) :4877-4879
[44]   Micro- and Nanocrystals of Organic Semiconductors [J].
Li, Rongjin ;
Hu, Wenping ;
Liu, Yunqi ;
Zhu, Daoben .
ACCOUNTS OF CHEMICAL RESEARCH, 2010, 43 (04) :529-540
[45]   A highly π-stacked organic semiconductor for thin film transistors based on fused thiophenes [J].
Li, XC ;
Sirringhaus, H ;
Garnier, F ;
Holmes, AB ;
Moratti, SC ;
Feeder, N ;
Clegg, W ;
Teat, SJ ;
Friend, RH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (09) :2206-2207
[46]   Highly Efficient Solar Cell Polymers Developed via Fine-Tuning of Structural and Electronic Properties [J].
Liang, Yongye ;
Feng, Danqin ;
Wu, Yue ;
Tsai, Szu-Ting ;
Li, Gang ;
Ray, Claire ;
Yu, Luping .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (22) :7792-7799
[47]   Facile Synthesis of Spirocyclic Aromatic Hydrocarbon Derivatives Based on o-Halobiaryl Route and Domino Reaction for Deep-Blue Organic Semiconductors [J].
Liu, Feng ;
Xie, Ling-Hai ;
Tang, Chao ;
Liang, Jing ;
Chen, Qing-Quan ;
Peng, Bo ;
Wei, Wei ;
Cao, Yong ;
Huang, Wei .
ORGANIC LETTERS, 2009, 11 (17) :3850-3853
[48]   The first single polymer with simultaneous blue, green, and red emission for white electroluminescence [J].
Liu, J ;
Zhou, QG ;
Cheng, YX ;
Geng, YH ;
Wang, LX ;
Ma, DG ;
Jing, XB ;
Wang, FS .
ADVANCED MATERIALS, 2005, 17 (24) :2974-+
[49]   Development of dendrimers: Macromolecules for use in organic light-emitting diodes and solar cells [J].
Lo, Shih-Chun ;
Burn, Paul L. .
CHEMICAL REVIEWS, 2007, 107 (04) :1097-1116
[50]   Synthesis, characterization, and transistor response of semiconducting silole polymers with substantial hole mobility and air stability. Experiment and theory [J].
Lu, Gang ;
Usta, Hakan ;
Risko, Chad ;
Wang, Lian ;
Facchetti, Antonio ;
Ratner, Mark A. ;
Marks, Tobin J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (24) :7670-7685