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Contents Vol 65(9)

Structure–Property Relationships Based on Phenyl-1H-Pyrrole End-Capped Thiophene Semiconductors

Ying Liu A B , Ji Zhang A , Yunqi Liu A C , Gui Yu A and Ziyi Ge B
+ Author Affiliations
- Author Affiliations

A Beijing National Laboratory for Molecular Sciences, Key Laboratory of Organic Solids, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China.

B Ningbo Institute of Material Technology and Engineering, Chinese Academy of Sciences, Ningbo 315201, China.

C Corresponding author. Email: liuyq@iccas.ac.cn

Australian Journal of Chemistry 65(9) 1252-1256 https://doi.org/10.1071/CH12112
Submitted: 22 February 2012  Accepted: 2 April 2012   Published: 29 June 2012

Abstract

Thiophene oligomers end-capped with phenyl-1H-pyrrole were used as active layers of organic field-effect transistors. Two types of cores that vary in size and shape of α-linked thiophenes and fused-ring thiophenes were chosen to study the structure–property relationship. The crystal structures, optical, electrochemical and electronic properties were investigated, and the heterocyclic compounds exhibited clear p-type semiconducting behavior.


References

[1]  (a) A. R. Murphy, J. M. J. Fréchet, Chem. Rev. 2007, 107, 1066.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXjvFyjsL0%3D&md5=851622bfa35f937aac3d5cffa7c566b4CAS |
      (b) J. E. Anthony, Chem. Rev. 2006, 106, 5028.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) W. P. Wu, Y. Q. Liu, D. B. Zhu, Chem. Soc. Rev. 2010, 39, 1489.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) Y. G. Wen, Y. Q. Liu, Adv. Mater. 2010, 22, 1331.
         | Crossref | GoogleScholarGoogle Scholar |

[2]  (a) C. Videlot-Ackermann, J. Ackermann, H. Brisset, K. Kawamura, N. Yoshimoto, P. Raynal, A. El Kassmi, F. Fages, J. Am. Chem. Soc. 2005, 127, 16346.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXhtFymsL3K&md5=c6294555773c5d91d1b5d328af977902CAS |
      (b) K. H. Kim, Z. Chi, M. J. Cho, J.-I. Jin, M. Y. Cho, S. J. Kim, J.-s. Joo, D. H. Choi, Chem. Mater. 2007, 19, 4925.
         | Crossref | GoogleScholarGoogle Scholar |

[3]  (a) H. Meng, J. Zheng, A. J. Lovinger, B. C. Wang, P. G. Van Patten, Z. N. Bao, Chem. Mater. 2003, 15, 1778.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXis1Khtbk%3D&md5=c50508735d81344f5e93fc1a4355298bCAS |
      (b) M. He, F. Zhang, J. Org. Chem. 2007, 72, 442.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) X.-C. Li, H. Sirringhaus, F. Garnier, A. B. Holmes, S. C. Moratti, N. Feeder, W. Clegg, S. J. Teat, R. H. Friend, J. Am. Chem. Soc. 1998, 120, 2206.
         | Crossref | GoogleScholarGoogle Scholar |

[4]  C. Y. Du, Y. L. Guo, Y. Q. Liu, W. F. Qiu, H. J. Zhang, X. K. Gao, Y. Liu, T. Qi, K. Lu, G. Yu, Chem. Mater. 2008, 20, 4188.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXmvVGqsb4%3D&md5=608beb14f6c8e8922e8576409c4bbd83CAS |

[5]  H. K. Tian, J. W. Shi, B. He, N. H. Hu, S. Q. Dong, D. H. Yan, J. P. Zhang, Y. H. Geng, F. S. Wang, Adv. Funct. Mater. 2007, 17, 1940.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXpvFCrt7c%3D&md5=7059a9c07332d87f660d6114a45f6d97CAS |

[6]  (a) Y. M. Sun, Y. W. Ma, Y. Q. Liu, Y. Y. Lin, Z. Y. Wang, Y. Wang, C. A. Di, K. Xiao, X. M. Chen, W. F. Qiu, B. Zhang, G. Yu, W. P. Hu, D. B. Zhu, Adv. Funct. Mater. 2006, 16, 426.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28Xhs1aksbw%3D&md5=855450e62ec6dbf80ed8d03ba8c77046CAS |
      (b) Y.-Y. Noh, R. Azumi, M. Goto, B.-J. Jung, E. Lim, H.-K. Shim, Y. Yoshida, K. Yase, D.-Y. Kim, Chem. Mater. 2005, 17, 3861.
         | Crossref | GoogleScholarGoogle Scholar |

[7]  Y. Liu, Y. Wang, W. P. Wu, Y. Q. Liu, H. X. Xi, L. M. Wang, W. F. Qiu, K. Lu, C. Y. Du, G. Yu, Adv. Funct. Mater. 2009, 19, 772.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXjs1yit7k%3D&md5=bb309276e3fb1c00ca4e2e4fbc77b679CAS |

[8]  (a) P. Liu, Y. Wu, H. Pan, Y. Li, S. Gardner, B. S. Ong, S. Zhu, Chem. Mater. 2009, 21, 2727.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXnt12nsbg%3D&md5=b314656a0a3455eb025957b0dad6941bCAS |
      (b) Q. Yuan, S. C. B. Mannsfeld, M. L. Tang, M. Roberts, M. F. Toney, D. M. DeLongchamp, Z. Bao, Chem. Mater. 2008, 20, 2763.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) M. L. Tang, M. E. Roberts, J. J. Locklin, M. M. Ling, H. Meng, Z. Bao, Chem. Mater. 2006, 18, 6250.
         | Crossref | GoogleScholarGoogle Scholar |

[9]  (a) F. Valiyev, W. S. Hu, H. Y. Chen, M. Y. Kuo, I. Chao, Y. T. Tao, Chem. Mater. 2007, 19, 3018.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXltFeqtbs%3D&md5=d64e530fb5cca18070540532b5004d28CAS |
      (b) J. Gao, R. Li, L. Li, Q. Meng, H. Jiang, H. Li, W. Hu, Adv. Mater. 2007, 19, 3008.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) B. Wex, B. R. Kaafarani, R. Schroeder, L. A. Majewski, P. Burckel, M. Grell, D. C. Neckers, J. Mater. Chem. 2006, 16, 1121.
         | Crossref | GoogleScholarGoogle Scholar |

[10]  (a) Y. Ma, Y. Sun, Y. Liu, J. Gao, S. Chen, X. Sun, W. Qiu, G. Yu, G. Cui, W. Hu, D. Zhu, J. Mater. Chem. 2005, 15, 4894.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXht1ems7zL&md5=b16471c92b04787e1f73a4b382438374CAS |
      (b) S. Wakim, J. Bouchard, M. Simard, N. Drolet, Y. Tao, M. Leclerc, Chem. Mater. 2004, 16, 4386.
         | Crossref | GoogleScholarGoogle Scholar |

[11]  Y. Wu, Y. Li, S. Gardner, B. S. Ong, J. Am. Chem. Soc. 2005, 127, 614.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXhtVKrs7%2FO&md5=39b6ca7160c9a708f88591dac5338158CAS |

[12]  J. W. W. Chang, X. Xu, P. W. H. Chan, Tetra. Lett. 2007, 48, 245.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XhtlahurfM&md5=3971f118058f4b045e445d38a9dc9428CAS |

[13]  S. Tavazzi, L. Miozzo, L. Silvestri, S. Mora, P. Spearman, M. Moret, S. Rizzato, D. Braga, A. Karim, D. Diaw, D. Gningue-Sall, J.-J. Aaron, A. Yassar, Cryst. Growth Des. 2010, 10, 2342.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXjvFeqsLc%3D&md5=48d4d932cc93648df646afc4a69f0a29CAS |

[14]  (a) S. T. Bromley, M. Mas-Torrent, P. Hadley, C. Rovira, J. Am. Chem. Soc. 2004, 126, 6544.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXjs12is7Y%3D&md5=4dab2594c6c3e14eb58a495e12dc526cCAS |
      (b) J. Cornil, J. Ph. Calbert, J. L. Bredas, J. Am. Chem. Soc. 2001, 123, 1250.
         | Crossref | GoogleScholarGoogle Scholar |

[15]  (a) J. L. Brédas, R. Silbey, D. S. Boudreaux, R. R. Chance, J. Am. Chem. Soc. 1983, 105, 6555.
         | Crossref | GoogleScholarGoogle Scholar |
      (b) H. Tian, J. Shi, D. Yan, L. Wang, Y. Geng, F. Wang, Adv. Mater. 2006, 18, 2149.
         | Crossref | GoogleScholarGoogle Scholar |