Free Standard AU & NZ Shipping For All Book Orders Over $80!
Register      Login
Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
Shopping Cart: ( empty )
You are here: Home > Journals > CH > CH11169
RESEARCH ARTICLE
Contents Vol 64(7)

Conjugated Oligomers and Polymers Based on Anthracene, Tetracene, Pentacene, Naphthodithiophene, and Anthradithiophene Building Blocks

Dan Lehnherr A and Rik R. Tykwinski B C
+ Author Affiliations
- Author Affiliations

A Department of Chemistry, University of Alberta, Edmonton, Alberta, T6G 2G2, Canada.

B Institut für Organische Chemie, Friedrich-Alexander-Universität Erlangen-Nürnberg, 91054 Erlangen, Germany.

C Corresponding author. Email: rik.tykwinski@chemie.uni-erlangen.de

Australian Journal of Chemistry 64(7) 919-929 https://doi.org/10.1071/CH11169
Submitted: 28 April 2011  Accepted: 24 May 2011   Published: 19 July 2011

Abstract

Acene derivatives provide unique materials for organic semiconductor applications. Recent synthetic achievements have provided several oligomers and polymers based on acene building blocks of varied structural motifs, including anthracene, tetracene, pentacene, as well as naphtho- and anthradithiophene. This report highlights recent work in this area, particularly for the higher acenes tetracene, pentacene, and anthradithiophene. When possible, the properties of defined-length oligomers are compared and contrasted to those of mono- and polymeric systems.


References

[1]  (a) J. E. Anthony, A. Facchetti, M. Heeney, S. R. Marder, X. W. Zhan, Adv. Mater. 2010, 22, 3876.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXhtFKlu7zF&md5=1bc7e9e0203c83c480fae46d670d9873CAS |
      (b) A. Pron, P. Gawrys, M. Zagorska, D. Djurado, R. Demadrille, Chem. Soc. Rev. 2010, 39, 2577.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) Y.-J. Cheng, S.-H. Yang, C.-S. Hsu, Chem. Rev. 2009, 109, 5868.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) A. R. Murphy, J. M. J. Fréchet, Chem. Rev. 2007, 107, 1066.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) M. Bendikov, F. Wudl, D. F. Perepichka, Chem. Rev. 2004, 104, 4891.
         | Crossref | GoogleScholarGoogle Scholar |

[2]  (a) J. E. Anthony, Angew. Chem. Int. Ed. 2008, 47, 452.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXptlOhtA%3D%3D&md5=efc255bc0f9dbdb8f522acc855f3a811CAS |
      (b) J. E. Anthony, Chem. Rev. 2006, 106, 5028.
         | Crossref | GoogleScholarGoogle Scholar |

[3]  (a) N. Franz, G. Kreutzer, H.-A. Klok, Synlett 2006, 1793.] (a)
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XhtVWntbjF&md5=35d32463477b7ba0a53740619eeb8223CAS |
         (b) (b) Electronic Materials – The Oligomer Approach 1998 (Eds K. Müllen, G. Wegner) (Wiley-VCH: Weinheim).

[4]  D. Lehnherr, R. R. Tykwinski, Materials 2010, 3, 2772.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXlsVyntL8%3D&md5=1484c072af7836e5b3f6befef4667b1eCAS |

[5]     (a) (a) For non-conjugated pentacene oligomers, see: D. Lehnherr, R. R. Tykwinski, Org. Lett. 2007, 9, 4583. https://doi.org/10.1021/Ol702094D
      (b) D. Lehnherr, R. McDonald, M. J. Ferguson, R. R. Tykwinski, Tetrahedron 2008, 64, 11449.For non-conjugated pentacene oligomers, see:
         | Crossref | GoogleScholarGoogle Scholar |
      (c) D. Lehnherr, J. Gao, F. A. Hegmann, R. R. Tykwinski, J. Org. Chem. 2009, 74, 5017.
         | Crossref | GoogleScholarGoogle Scholar |

[6]  R. E. Martin, F. Diederich, Angew. Chem. Int. Ed. 1999, 38, 1350.
         | Crossref | GoogleScholarGoogle Scholar |

[7]  (a) K. Ito, T. Suzuki, Y. Sakamoto, D. Kubota, Y. Inoue, F. Sato, S. Tokito, Angew. Chem. Int. Ed. 2003, 42, 1159.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXisVers7o%3D&md5=d6ed2a7870ea5907fda02a05f915c6a9CAS |
      (b) W. Cui, X. Zhang, X. Jiang, H. Tian, D. Yan, Y. Geng, X. Jing, F. Wang, Org. Lett. 2006, 8, 785.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) A. Dell'Aquila, F. Marinelli, J. Tey, P. Keg, Y.-M. Lam, O. L. Kapitanchuk, P. Mastrorilli, C. F. Nobile, P. Cosma, A. Marchenko, D. Fichou, S. G. Mhaisalkar, G. P. Suranna, L. Torsi, J. Mater. Chem. 2008, 18, 786.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) P. Keg, A. Dell'Aquila, F. Marinelli, O. L. Kapitanchuk, D. Fichou, P. Mastrorilli, G. Romanazzi, G. P. Suranna, L. Torsi, Y. M. Lam, S. G. Mhaisalkar, J. Mater. Chem. 2010, 20, 2448.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) S. Akiyama, S. Misumi, M. Nakagawa, Bull. Chem. Soc. Jpn. 1960, 33, 1293.
         | Crossref | GoogleScholarGoogle Scholar |
      (f) W. Zhao, Q. Tang, H. S. Chan, J. Xu, K. Y. Lo, Q. Miao, Chem. Commun. 2008, 4324.
         | Crossref | GoogleScholarGoogle Scholar |
      (g) J. A. Merlo, C. R. Newman, C. P. Gerlach, T. W. Kelley, D. V. Muyres, S. E. Fritz, M. F. Toney, C. D. Frisbie, J. Am. Chem. Soc. 2005, 127, 3997.
         | Crossref | GoogleScholarGoogle Scholar |
      (h) S. Toyota, M. Goichi, M. Kotani, Angew. Chem. Int. Ed. 2004, 43, 2248.
         | Crossref | GoogleScholarGoogle Scholar |
      (i) S. Toyota, Chem. Lett. 2011, 40, 12.
         | Crossref | GoogleScholarGoogle Scholar |
      (j) Y. Morisaki, T. Sawamura, T. Murakami, Y. Chujo, Org. Lett. 2010, 12, 3188.
         | Crossref | GoogleScholarGoogle Scholar |

[8]  (a) M. Baumgarten, U. Müller, A. Bohnen, K. Müllen, Angew. Chem. Int. Ed. Engl. 1992, 31, 448.
         | Crossref | GoogleScholarGoogle Scholar |
      (b) U. Müller, A. Martin, K. Müllen, Chem. Ber. 1994, 127, 437.
         | Crossref | GoogleScholarGoogle Scholar |

[9]  (a) M. Roth, M. Rehahn, M. Ahles, R. Schmechel, H. von Seggern, Mater. Res. Soc. Symp. Proc. 2005, 871E, I6.29.1.
      (b) A. M. Müller, Y. S. Avlasevich, W. W. Schoeller, K. Müllen, C. J. Bardeen, J. Am. Chem. Soc. 2007, 129, 14240.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) A. M. Müller, Y. S. Avlasevich, K. Müllen, C. J. Bardeen, Chem. Phys. Lett. 2006, 421, 518.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) T. Kimoto, K. Tanaka, Y. Sakai, A. Ohno, K. Yoza, K. Kobayashi, Org. Lett. 2009, 11, 3658.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) V. S. Barlier, C. W. Schlenker, S. W. Chin, M. E. Thompson, Chem. Commun. 2011, 47, 3754.
         | Crossref | GoogleScholarGoogle Scholar |

[10]  S. A. Odom, S. R. Parkin, J. E. Anthony, Org. Lett. 2003, 5, 4245.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXotVWqtbc%3D&md5=d41e746a62392cabe35bc4da16cba81dCAS |

[11]  X. Zhang, X. Jiang, J. Luo, C. Chi, H. Chen, J. Wu, Chem. Eur. J. 2010, 16, 464.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXjvFSh&md5=403ad6cddfb3b48544cb4c275aee02cdCAS |

[12]  J. E. Anthony, J. S. Brooks, D. L. Eaton, S. R. Parkin, J. Am. Chem. Soc. 2001, 123, 9482.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXmt1Olurg%3D&md5=682c548ef798ad18c8cbe7dd25090da2CAS |

[13]  D. Lehnherr, J. Gao, F. A. Hegmann, R. R. Tykwinski, Org. Lett. 2008, 10, 4779.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXhtF2lsrrK&md5=d806bab7fc106f4adbb0972861491651CAS |

[14]  D. Lehnherr, A. H. Murray, R. McDonald, M. J. Ferguson, R. R. Tykwinski, Chem. Eur. J. 2009, 15, 12580.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXhsVKgtrbK&md5=d6ea36260f407042f0f344218b03653aCAS |

[15]  I. H. Campbell, B. K. Crone, J. Appl. Phys. 2007, 101, 024502.
         | Crossref | GoogleScholarGoogle Scholar |

[16]  J. Gao, F. A. Hegmann, Appl. Phys. Lett. 2008, 93, 223306.
         | Crossref | GoogleScholarGoogle Scholar |

[17]  D. Lehnherr, A. H. Murray, R. McDonald, R. R. Tykwinski, Angew. Chem. Int. Ed. 2010, 49, 6190.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXhtVejsr7M&md5=d95a9e48147a20e581fab6a146f66310CAS |

[18]  (a) H. Pang, F. Vilela, P. J. Skabara, J. J. W. McDouall, D. J. Crouch, T. D. Anthopoulos, D. D. C. Bradley, D. M. de Leeuw, P. N. Horton, M. B. Hursthouse, Adv. Mater. 2007, 19, 4438.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXhtVWnu74%3D&md5=acf6d56717ad6409f2050841892ac8a6CAS |
      (b) T. Vehoff, B. Baumeier, A. Troisi, D. Andrienko, J. Am. Chem. Soc. 2010, 132, 11702.
         | Crossref | GoogleScholarGoogle Scholar |

[19]     (a) (a) For a selection of anthracene-based polymers, see: M. W. Pelter, J. K. Stille, Macromolecules 1990, 23, 2418. https://doi.org/10.1021/MA00211A002
      (b) P. Hodge, G. A. Power, M. A. Rabjohns, Chem. Commun. 1997, 73.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) W. Cui, Y. Wu, H. Tian, Y. Geng, F. Wang, Chem. Commun. 2008, 1017.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) W. Cui, Y. Zhao, H. Tian, Z. Xie, Y. Geng, F. Wang, Macromolecules 2009, 42, 8021.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) J.-H. Park, D. S. Chung, D. H. Lee, H. Kong, I. H. Jung, M.-J. Park, N. S. Cho, C. E. Park, H.-K. Shim, Chem. Commun. 2010, 46, 1863.
         | Crossref | GoogleScholarGoogle Scholar |
      (f) D. A. M. Egbe, S. Türk, S. Rathgeber, F. Kühnlenz, R. Jadhav, A. Wild, E. Birckner, G. Adam, A. Pivrikas, V. Cimrova, G. Knör, N. S. Sariciftci, H. Hoppe, Macromolecules 2010, 43, 1261.
         | Crossref | GoogleScholarGoogle Scholar |
      (g) D. A. M. Egbe, B. Cornelia, J. Nowotny, W. Günther, E. Klemm, Macromolecules 2003, 36, 5459.
         | Crossref | GoogleScholarGoogle Scholar |
      (h) M. S. Taylor, T. M. Swager, Angew. Chem. Int. Ed. 2007, 46, 8480.
         | Crossref | GoogleScholarGoogle Scholar |
      (i) S. Tokito, K.-H. Weinfurtner, H. Fujikawa, T. Tsutsui, Y. Taga, Proc. SPIE-Int. Soc. Opt. Eng. 2001, 4105, 69.

[20]  T. Okamoto, Z. Bao, J. Am. Chem. Soc. 2007, 129, 10308.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXos1ensbk%3D&md5=724c435e9250355e67a0148eda3644b7CAS |

[21]  T. Okamoto, Y. Jiang, F. Qu, A. C. Mayer, J. E. Parmer, M. D. McGehee, Z. Bao, Macromolecules 2008, 41, 6977.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXhtFaitLfP&md5=fd0c55b97f210c3ca13dc720761b09fdCAS |

[22]  G. P. Miller, J. Mack, Org. Lett. 2000, 2, 3979.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3cXotVakurk%3D&md5=77370ff98e4c476b95ceab419b14c6a5CAS |

[23]  T. Okamoto, Y. Jiang, H. A. Becerril, S. Hong, M. L. Senatore, M. L. Tang, M. F. Toney, T. Siegrist, Z. Bao, J. Mater. Chem 2011, 21, 7078.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXlsV2nsrY%3D&md5=0749e092aa86b4200953904b254fb05fCAS |

[24]  Y. Jiang, T. Okamoto, H. A. Becerril, S. Hong, M. L. Tang, A. C. Mayer, J. E. Parmer, M. D. McGehee, Z. Bao, Macromolecules 2010, 43, 6361.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXosleitbY%3D&md5=396e8c15c567f82a79467bdcdf309239CAS |

[25]  J.-Y. Balandier, F. Quist, S. Stas, B. Tylleman, C. Ragoen, A. Mayence, S. Bouzakraoui, J. Cornil, Y. H. Geerts, Org. Lett. 2011, 13, 548.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXit1aruw%3D%3D&md5=ce0d15048a4eef4251cd27542edcf915CAS |

[26]  I. Osaka, T. Abe, S. Shinamura, K. Takimiya, J. Am. Chem. Soc. 2011, 133, 6852.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXksVeitbo%3D&md5=6953a206e85ab975d1c42d244abeffdfCAS |

[27]  S. Shinamura, I. Osaka, E. Miyazaki, A. Nakao, M. Yamagishi, J. Takeya, K. Takimiya, J. Am. Chem. Soc. 2011, 133, 5024.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXivFyhtro%3D&md5=2091f85d466c7d39302e66d443b8d404CAS |

[28]  J. E. Anthony, J. Gierschner, C. A. Landis, S. R. Parkin, J. B. Sherman, R. C. Bakus, Chem. Commun. 2007, 4746.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXhtlSmurfL&md5=264f402f88c3ee7751542280105281f8CAS |

[29]  For the initial report of compound 65, see: Payne  M. M.Odom  S. A.Parkin  S. R.Anthony  J. E.Org. Lett. 2004, 6 3325. 10.1021/OL048686D

[30]  I. Kaur, W. Jia, R. P. Kopreski, S. Selvarasah, M. R. Dokmeci, C. Pramanik, N. E. McGruer, G. P. Miller, J. Am. Chem. Soc. 2008, 130, 16274.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXhtlOrs73L&md5=7e9f58a43ceb30afa03418ce90fe04f0CAS |

[31]  B. M. Medina, J. E. Anthony, J. Gieschner, ChemPhysChem 2008, 9, 1519.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXpvVOnt7w%3D&md5=757a58416584de6af58de5e0d218154bCAS |