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

Why Do Some Alkoxybromothiophenes Spontaneously Polymerize?

Pawel Wagner A , Kenneth W. Jolley B and David L. Officer A C
+ Author Affiliations
- Author Affiliations

A Intelligent Polymer Research Centre and ARC Centre of Excellence for Electromaterial Sciences, AIIM Facility, Innovation Campus, University of Wollongong, Wollongong, NSW 2522, Australia.

B Nanomaterials Research Centre and MacDiarmid Institute for Advanced Materials, Massey University, Private Bag 11222, Palmerston North, New Zealand.

C Corresponding author. Email: davido@uow.edu.au

Australian Journal of Chemistry 64(3) 335-338 https://doi.org/10.1071/CH10413
Submitted: 12 November 2010  Accepted: 25 January 2011   Published: 11 March 2011

Abstract

Neat liquid 3-alkoxy-2-bromothiophenes such as 2-bromo-EDOT have been shown to autopolymerize at room temperature and above, depending on their proton acidity and the nature and arrangement of substituents.


References

[1]  G. G. Wallace, G. M. Spinks, L. A. P. Kane-Maguire, P. R. Teasdale, Conductive Electroactive Polymers, 3rd edn 2009 (CRC Press LLC: Boca Raton).

[2]  Handbook of Conducting Polymers, 3rd edn (Eds T. A. Skotheim, J. R. Reynolds) 2007 (CRC Press: Boca Raton).

[3]  G. Barbarella, M. Melucci, G. Sotgiu, Adv. Mater. (Deerfield Beach Fla.) 2005, 17, 1581.
         | CrossRef | 1:CAS:528:DC%2BD2MXmtlCjtbg%3D&md5=254e09f554b46b13cd8aeb350c2524dbCAS |

[4]  N. J. L. Guernion, W. Hayes, Curr. Org. Chem. 2004, 8, 637.
         | CrossRef | 1:CAS:528:DC%2BD2cXjt1emu7k%3D&md5=0863db57495f2c14764a799cc9a78259CAS |

[5]  H. Meng, D. F. Perepichka, F. Wudl, Angew. Chem. Int. Ed. 2003, 42, 658.
         | CrossRef | 1:CAS:528:DC%2BD3sXhs1Sitbk%3D&md5=bffef3e99a28da3a73a38e87ee2740ebCAS |

[6]  H. Meng, D. F. Perepichka, M. Bendikov, F. Wudl, G. Z. Pan, W. Yu, W. Dong, S. Brown, J. Am. Chem. Soc. 2003, 125, 15151.
         | CrossRef | 1:CAS:528:DC%2BD3sXovVOis7o%3D&md5=75cb9ee297e4c95573b2ba712f19e560CAS | 14653750PubMed |

[7]  H. J. Spencer, R. Berridge, D. J. Crouch, S. P. Wright, M. Giles, I. McCulloch, S. J. Coles, M. B. Hursthouse, P. J. Skabara, J. Mater. Chem. 2003, 13, 2075.
         | CrossRef | 1:CAS:528:DC%2BD3sXmsFWhtr0%3D&md5=22f59dd0386118d484368a27db4cdf11CAS |

[8]  G. E. Collis, A. K. Burrell, S. M. Scott, D. L. Officer, J. Org. Chem. 2003, 68, 8974.
         | CrossRef | 1:CAS:528:DC%2BD3sXot1Ojur4%3D&md5=af17cb547af64b8a8296711463f736a2CAS | 14604370PubMed |

[9]  D. K. Grant, K. W. Jolley, D. L. Officer, K. C. Gordon, T. M. Clarke, Org. Biomol. Chem. 2005, 3, 2008.
         | CrossRef | 1:CAS:528:DC%2BD2MXktFWlur8%3D&md5=e26fc8569dd39d6c78d14fd8ee19960eCAS | 15889185PubMed |

[10]  P. Wagner, A. M. Ballantyne, K. W. Jolley, D. L. Officer, Tetrahedron 2006, 62, 2190.
         | CrossRef | 1:CAS:528:DC%2BD28XhvVSisbs%3D&md5=f9df2f532e754b472adad4813d6d6eaeCAS |

[11]  F. Demanze, A. Yassar, F. Garnier, Macromol. 1996, 29, 4267.
         | CrossRef | 1:CAS:528:DyaK28XivFShtr4%3D&md5=8c106b26e7e29fd5efba6558b045c360CAS |

[12]  M. BelletĂȘte, S. Beaupre, J. Bouchard, P. Blondin, M. Leclere, G. Durocher, J. Phys. Chem. B 2000, 104, 9118.
         | CrossRef |

[13]  Y. Zhu, M. O. Wolf, J. Am. Chem. Soc. 2000, 122, 10121.
         | CrossRef | 1:CAS:528:DC%2BD3cXmvValsrk%3D&md5=e61d274ff15c55d77ef367688c62a9d1CAS |

[14]  W.-P. Baik, Y.-S. Kim, J.-H. Park, S.-G. Jung, US Patent Application No. 20040171790 2004.

[15]  P. Audebert, G. Bidan, Synth. Met. 1986, 15, 9.
         | CrossRef | 1:CAS:528:DyaL28XltlCltr0%3D&md5=d96841619dc4df4360b86b82034fb4e9CAS |

[16]  T. J. Wallace, F. A. Baron, J. Org. Chem. 1965, 30, 3520.
         | CrossRef | 1:CAS:528:DyaF2MXkvVSjtL0%3D&md5=d30b4288b6c6b7dd409b40ffd19a2b78CAS |

[17]  Y. Yu, E. Gunic, B. Zinger, L. L. Miller, J. Am. Chem. Soc. 1996, 118, 1013.
         | CrossRef | 1:CAS:528:DyaK28Xks1yrtw%3D%3D&md5=5a0428fd6f7cb62b8aab68e4857190a5CAS |



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