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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Synthesis and Physical Properties of Hyperbranched Polymers Containing Twisted Acenes

Xuemin Zhang A , Hongtao Song A , Jinchong Xiao A B , Tiejun Ren A , Sujuan Wang A , Zhenying Liu A , Xinwu Ba A and Yonggang Wu A B
+ Author Affiliations
- Author Affiliations

A College of Chemistry and Environment Science, Key Laboratory of Chemical Biology of Hebei Province, Hebei University, Baoding 071002, China.

B Corresponding authors. Email: jcxiaoiccas@gmail.com; wuyonggang@iccas.ac.cn

Australian Journal of Chemistry 68(3) 505-512 https://doi.org/10.1071/CH14322
Submitted: 21 May 2014  Accepted: 9 July 2014   Published: 30 September 2014

Abstract

Novel hyperbranched co-polymers HP1HP4 with twisted acene units and truxene groups have been synthesised through Suzuki coupling reaction and characterised. Single crystal analyses showed that the model compounds 3 and 5 had twisted structures with torsion angles of 40.73° and 28.65°, respectively. The polymers show blue light emission in organic solvents and thin films, as well as high stability, which might be utilised as potential candidates for organic electronic materials.


References

[1]  (a) M. Bendikov, F. Wudl, Chem. Rev. 2004, 104, 4891.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXovFSmtbw%3D&md5=0d52a5e77f5e33a334f2acf0446c1b63CAS | 15535637PubMed |
      (b) J. E. Anthony, Chem. Rev. 2006, 106, 5028.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) K. Walzer, B. Maennig, M. Pfeiffer, K. Leo, Chem. Rev. 2007, 107, 1233.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) J. Xiao, B. Yang, J. I. Wong, Y. Liu, F. Wei, K. J. Tan, X. Teng, Y. Wu, L. Huang, C. Kloc, F. Boey, J. Ma, H. Zhang, H. Yang, Q. Zhang, Org. Lett. 2011, 13, 3004.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) D. Liu, Q. Li, R. Wang, Aust. J. Chem. 2013, 66, 594.
         | Crossref | GoogleScholarGoogle Scholar |

[2]  (a) Y. Guo, Q. Tang, H. Liu, Y. Zhang, Y. Li, W. Hu, S. Wang, D. Zhu, J. Am. Chem. Soc. 2008, 130, 9198.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXnvF2htro%3D&md5=832399f7271166fa109c69a93637f967CAS | 18588295PubMed |
      (b) X. Qian, H. Liu, N. Chen, H. Zhou, L. Sun, Y. Li, Y. Li, Inorg. Chem. 2012, 51, 677.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) W. Yuan, Z. Yu, Y. Tang, J. W. Y. Lam, N. Xie, P. Lu, E. Q. Chen, B. Z. Tang, Macromolecules 2011, 44, 9618.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) C. Wang, K. Wang, Q. Fu, J. Zhang, D. Ma, Y. Wang, J. Mater. Chem. C 2013, 1, 410.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) Y. Zhao, J. Chen, D. Ma, ACS Appl. Mater. Interfaces 2013, 5, 965.
         | Crossref | GoogleScholarGoogle Scholar |

[3]  (a) T. Lei, J. Dou, X. Cao, J. Wang, J. Pei, J. Am. Chem. Soc. 2013, 135, 12168.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXnslWlsrw%3D&md5=b9a4ebfa4caf3853030da190652b6514CAS | 23675890PubMed |
      (b) S. Xiao, S. J. Kang, Y. Wu, S. Ahn, J. B. Kim, Y. L. Loo, T. Siegrist, M. L. Steiger, H. Li, C. Nuckolls, Chem. Sci. 2013, 4, 2018.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) J. Mei, Y. Diao, A. L. Appleton, L. Fang, Z. Bao, J. Am. Chem. Soc. 2013, 135, 6724.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) C. J. Bettinger, Z. Bao, Adv. Mater. 2010, 22, 651.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) P. Gu, F. Zhou, J. Gao, G. Li, C. Wang, Q. Xu, Q. Zhang, J. Lu, J. Am. Chem. Soc. 2013, 135, 14086.
         | Crossref | GoogleScholarGoogle Scholar |
      (f) J. Xiao, Y. Azuma, Y. Liu, G. Li, F. Wei, K. J. Tan, C. Kloc, H. Zhang, Y. Majima, Q. Zhang, Aust. J. Chem. 2012, 65, 1674.
         | Crossref | GoogleScholarGoogle Scholar |

[4]  (a) Y. Li, Acc. Chem. Res. 2012, 45, 723.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XhsVyrtr0%3D&md5=a947d24ed01060c8c05ba28c3ca8e237CAS | 22288572PubMed |
      (b) J. E. Coughlin, Z. B. Henson, G. C. Welch, G. C. Bazan, Acc. Chem. Res. 2014, 47, 257.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) X. Gong, C. Li, Z. Lu, G. Li, Q. Mei, T. Fang, Z. Bo, Macromol. Rapid Commun. 2013, 34, 1163.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) T. Ren, J. Xiao, W. Wang, W. Xu, S. Wang, X. Zhang, X. Wang, H. Chen, J. Zhao, L. Jiang, Chem. – Asian J. 2014, 9, 1943.
         | Crossref | GoogleScholarGoogle Scholar |

[5]  (a) L. Feng, C. Zhu, H. Yuan, L. Liu, F. Lv, S. Wang, Chem. Soc. Rev. 2013, 42, 6620.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhtFeqtrfN&md5=00f075db54cf5287da960ac5df193a91CAS | 23744297PubMed |
      (b) C. Zhu, L. Liu, Q. Yang, F. Lv, S. Wang, Chem. Rev. 2012, 112, 4687.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) C. A. Traina, R. C. Bakus, G. C. Bazan, J. Am. Chem. Soc. 2011, 133, 12600.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) Y. Wang, J. Xiao, S. Wang, B. Yang, X. Ba, Supramol. Chem. 2010, 22, 380.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) Y. Zhao, Y. Li, Y. Li, H. Zheng, X. Yin, H. Liu, Chem. Commun. 2010, 46, 5698.
         | Crossref | GoogleScholarGoogle Scholar |
      (f) D. Ding, K. Li, B. Liu, B. Z. Tang, Acc. Chem. Res. 2013, 46, 2441.
         | Crossref | GoogleScholarGoogle Scholar |

[6]  C. Wang, K. Wang, Q. Fu, J. Zhang, D. Ma, Y. Wang, J. Mater. Chem. C 2013, 1, 410.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XhvVeltrrK&md5=ec55cd47feedc1032eaee9b23cdd4cb7CAS |

[7]  (a) J. Luo, Z. Xie, J. W. Y. Lam, L. Cheng, H. Chen, C. Qiu, H. S. Kwok, X. Zhan, Y. Liu, D. Zhu, B. Tang, Chem. Commun. 2001, 1740.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXmvFCitrw%3D&md5=61217af9348220011ee655e2ee69a581CAS |
      (b) Y. Hong, J. W. Y. Lam, B. Z. Tang, Chem. Soc. Rev. 2011, 40, 5361.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) B. K. An, J. Gierschner, S. Y. Park, Acc. Chem. Res. 2012, 45, 544.
         | Crossref | GoogleScholarGoogle Scholar |

[8]  (a) J. Xiao, H. M. Duong, Y. Liu, W. Shi, L. Ji, G. Li, S. Li, X. Liu, J. Ma, F. Wudl, Q. Zhang, Angew. Chem. Int. Ed. 2012, 51, 6094.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38Xms1enu7Y%3D&md5=631ef1184ba66deaf655f230080436a5CAS |
      (b) J. Xiao, S. Liu, Y. Liu, L. Ji, X. Liu, H. Zhang, X. Sun, Q. Zhang, Chem.­– Asian J. 2012, 7, 561.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) J. Xiao, C. D. Malliakas, Y. Liu, F. Zhou, G. Li, H. Su, M. G. Kanatzidis, F. Wudl, Q. Zhang, Chem. – Asian J. 2012, 7, 672.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) J. Xiao, Y. Divayana, Q. Zhang, H. M. Doung, H. Zhang, F. Boey, X. W. Sun, F. Wudl, J. Mater. Chem. 2010, 20, 8167.
         | Crossref | GoogleScholarGoogle Scholar |

[9]  (a) Q. Pei, Y. Yang, J. Am. Chem. Soc. 1996, 118, 7416.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK28XktlGhsLk%3D&md5=18b5c4f45335d7cd93777e929ff037c3CAS |
      (b) F. Huang, H. Wu, D. Wang, W. Yang, Y. Cao, Chem. Mater. 2004, 16, 708.
         | Crossref | GoogleScholarGoogle Scholar |

[10]  (a) J. H. Burroughes, D. D. C. Bradley, A. R. Brown, R. N. Marks, K. Mackay, R. H. Friend, P. L. Burns, A. B. Holmes, Nature 1990, 347, 539.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3cXmt1Sru7o%3D&md5=deffd4243513f0405c684798f7da54acCAS |
      (b) H. L. Chow, K. F. Lin, D. C. Wang, J. Polym. Sci., Part B: Polym. Phys. 2006, 44, 62.
         | Crossref | GoogleScholarGoogle Scholar |

[11]  (a) Y. Yang, Q. Pei, A. J. Heeger, J. Appl. Phys. 1996, 79, 934.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK28XltFKnsA%3D%3D&md5=873f53f7ac63bd7d0daea23cb7bcd77aCAS |
      (b) I. K. Spiliopoulos, J. A. Mikroyannidis, J. Polym. Sci., Part A: Polym. Chem. 2002, 40, 2591.
         | Crossref | GoogleScholarGoogle Scholar |

[12]  J. Pei, W. L. Yu, J. Ni, Y. H. Lai, W. Huang, A. J. Heeger, Macromolecules 2001, 34, 7241.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXms1Cltb8%3D&md5=0d9fd802841ddba13251aa34caadb230CAS |

[13]  C. Yang, H. Scheiber, E. J. W. List, J. Jacob, K. Müllen, Macromolecules 2006, 39, 5213.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28Xmsl2ktrw%3D&md5=1cda6676ed825608dfd9c34761c44bbeCAS |

[14]  Z. Liu, J. Xiao, Q. Fu, H. Feng, X. Zhang, T. Ren, S. Wang, D. Ma, X. Wang, H. Chen, ACS Appl. Mater. Interfaces 2013, 5, 11136.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhs1CgsbzF&md5=31bef45fe9c623b2a7584da1140e8841CAS | 24144121PubMed |

[15]  Y. Wu, X. Hao, J. Wu, J. Jin, X. Ba, Macromolecules 2010, 43, 731.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXhs1WltrbP&md5=2c30a282ef8bc9ab1d131be2ba9fbd77CAS |

[16]  V. Coropceanu, J. Cornil, D. A. da Silva Filho, Y. Olivier, R. Silbey, J. L. Brédas, Chem. Rev. 2007, 107, 926.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXjt1ymsb8%3D&md5=25f6dab53ff1c70b3691377ff1035c83CAS | 17378615PubMed |