A Modular Synthetic Approach to Conjugated Pentacene Di-, Tri-, and Tetramers

被引:69
作者
Lehnherr, Dan [1 ]
Murray, Adrian H. [1 ]
McDonald, Robert [1 ]
Tykwinski, Rik R. [1 ]
机构
[1] Univ Alberta, Dept Chem, Xray Crystallog Lab, Edmonton, AB T6G 2G2, Canada
关键词
acenes; C-C coupling; oligomerization; pi interactions; semiconductors; OLIGOMERS; ACENES; STATE; POLYMERS;
D O I
10.1002/anie.201000555
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Mind the band gap: π-conjugated pentacene di-, tri-, and tetramers can be synthesized by using a versatile building block in Hay homocoupling as well as Cadiot-Chodkiewicz cross-coupling reactions. This modular approach allows the evaluation of solubility, stability, and the HOMO-LUMO gap as a function of compound length. Long-range three-dimensional π overlap occurs in the iBu3Si-substituted pentacene dimer (see figure; n=2). © 2010 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:6190 / 6194
页数:5
相关论文
共 44 条
[21]   Synthesis, structure, and resolution of exceptionally twisted pentacenes [J].
Lu, Jun ;
Ho, Douglas M. ;
Vogelaar, Nancy J. ;
Kraml, Christina M. ;
Bernhard, Stefan ;
Byrne, Neal ;
Kim, Laura R. ;
Pascal, Robert A., Jr. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (51) :17043-17050
[22]  
Martin R.E., 1999, ANGEW CHEMIE, V111, P1440
[23]  
Martin RE, 1999, ANGEW CHEM INT EDIT, V38, P1350, DOI 10.1002/(SICI)1521-3773(19990517)38:10<1350::AID-ANIE1350>3.0.CO
[24]  
2-6
[25]   Conjugated oligomers with terminal donor-acceptor substitution [J].
Meier, H .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (17) :2482-2506
[26]  
Meier H., 2005, Angew. Chem., V117, P2536
[27]   Organization of acenes with a cruciform assembly motif [J].
Miao, Q ;
Chi, XL ;
Xiao, SX ;
Zeis, R ;
Lefenfeld, M ;
Siegrist, T ;
Steigerwald, ML ;
Nuckolls, C .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (04) :1340-1345
[28]   Synthesis and characterization of pentacene- and anthradithiophene-fluorene conjugated copolymers synthesized by Suzuki reactions [J].
Okamoto, Toshihiro ;
Jiang, Ying ;
Qu, Fei ;
Mayer, Alex C. ;
Parmer, Jack E. ;
McGehee, Michael D. ;
Bao, Zhenan .
MACROMOLECULES, 2008, 41 (19) :6977-6980
[29]   Synthesis of solution-soluble pentacene-containing conjugated copolymers [J].
Okamoto, Toshihiro ;
Bao, Zhenan .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (34) :10308-+
[30]   Advantageous 3D ordering of π-conjugated systems:: A new approach towards efficient charge transport any direction [J].
Pang, Hao ;
Vilela, Filipe ;
Skabara, Peter J. ;
McDouall, Joseph J. W. ;
Crouch, David J. ;
Anthopoulos, Thomas D. ;
Bradley, Donal D. C. ;
De Leeuw, Dago M. ;
Horton, Peter N. ;
Hursthouse, Michael B. .
ADVANCED MATERIALS, 2007, 19 (24) :4438-+