Synthesis and properties of thienopyrrole based heteroacenes - indolodibenzothienopyrrole and dicarbazolodithienopyrrole

被引:10
作者
Balaji, Ganapathy [1 ]
Della Pelle, Andrea M. [1 ]
Popere, Bhooshan C. [1 ]
Chandrasekaran, A. [1 ]
Thayumanavan, S. [1 ]
机构
[1] Univ Massachusetts, Dept Chem, Amherst, MA 01003 USA
关键词
FIELD-EFFECT TRANSISTORS; ORGANIC SEMICONDUCTORS; TRANSPORT-PROPERTIES; CHARGE-TRANSPORT; HIGH-PERFORMANCE; DERIVATIVES; THIOPHENE; ACENES; ROUTE;
D O I
10.1039/c2ob25087j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We report the syntheses and properties of thienopyrrole based unsymmetrical and extended heteroacenes, which are isoelectronic with heptacene (30 pi) and nonacene (38 pi), respectively. Optical and electrochemical properties of these seven and nine rings fused systems are studied. The optoelectronic properties of the syn and anti-isomers of the unsymmetrical heteroacenes are also compared. The influence of the position of the heteroatoms in the fused corona, upon the optical and electrochemical properties, is rationalized based on the contributions from the benzenoid vs. quinonoid-type structures of these molecules.
引用
收藏
页码:3455 / 3462
页数:8
相关论文
共 49 条
[41]   Synthesis and properties of the anti and syn isomers of dibenzothieno[b,d]pyrrole [J].
Qi, Ting ;
Guo, Yunlong ;
Liu, Yunqi ;
Xi, Hongxia ;
Zhang, Hengjun ;
Gao, Xike ;
Liu, Ying ;
Lu, Kun ;
Du, Chunyan ;
Yu, Giu ;
Zhu, Daoben .
CHEMICAL COMMUNICATIONS, 2008, (46) :6227-6229
[42]   Dually Switchable Heterotetracenes: Addressing the Photophysical Properties and Self-Organization of the P-S System [J].
Ren, Yi ;
Baumgartner, Thomas .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (05) :1328-1340
[43]  
RONALD GH, 1997, POLYCYCLIC AROMATIC
[44]   Synthetic principles for bandgap control in linear pi-conjugated systems [J].
Roncali, J .
CHEMICAL REVIEWS, 1997, 97 (01) :173-205
[45]   Linear- and Angular-Shaped Naphthodithiophenes: Selective Synthesis, Properties, and Application to Organic Field-Effect Transistors [J].
Shinamura, Shoji ;
Osaka, Itaru ;
Miyazaki, Eigo ;
Nakao, Akiko ;
Yamagishi, Masakazu ;
Takeya, Jun ;
Takimiya, Kazuo .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (13) :5024-5035
[46]   2,7-Diphenyl[1]benzothieno[3,2-b]benzothiophene, a new organic semiconductor for air-stable organic field-effect transistors with mobilities up to 2.0 cm2 V-1 s-1 [J].
Takimiya, Kazuo ;
Ebata, Hideaki ;
Sakamoto, Katsuhiro ;
Izawa, Takafumi ;
Otsubo, Tetsuo ;
Kunugi, Yoshihito .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (39) :12604-12605
[47]   New organic semiconductors and their device performance as a function of thiophene orientation [J].
Wex, B ;
Kaafarani, BR ;
Schroeder, R ;
Majewski, LA ;
Burckel, P ;
Grell, M ;
Neckers, DC .
JOURNAL OF MATERIALS CHEMISTRY, 2006, 16 (12) :1121-1124
[48]   Ladder π-conjugated materials with main group elements [J].
Yamaguchi, S ;
Xu, CH ;
Okamoto, T .
PURE AND APPLIED CHEMISTRY, 2006, 78 (04) :721-730
[49]   Single microwire transistors of oligoarenes by direct solution process [J].
Zhou, Yan ;
Liu, Wen-Jun ;
Ma, Yuguo ;
Wang, Hailiang ;
Qi, Limin ;
Cao, Yong ;
Wang, Jian ;
Pei, Jian .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (41) :12386-+