CSIRO Publishing blank image blank image blank image blank imageBooksblank image blank image blank image blank imageJournalsblank image blank image blank image blank imageAbout Usblank image blank image blank image blank imageShopping Cartblank image blank image blank image You are here: Journals > Australian Journal of Chemistry   
Australian Journal of Chemistry
Journal Banner
  An international journal for chemical science
 
blank image Search
 
blank image blank image
blank image
 
  Advanced Search
   

Journal Home
About the Journal
Editorial Structure
Contacts
For Advertisers
Content
Online Early
Current Issue
Just Accepted
All Issues
Virtual Issues
Special Issues
Research Fronts
Sample Issue
Covers
For Authors
General Information
Scope
Submit Article
Author Instructions
Open Access
For Referees
Referee Guidelines
Review an Article
For Subscribers
Subscription Prices
Customer Service
Print Publication Dates

blue arrow e-Alerts
blank image
Subscribe to our Email Alert or RSS feeds for the latest journal papers.

red arrow Connect with us
blank image
facebook twitter LinkedIn

Affiliated with RACI

Royal Australian Chemical Institute
Royal Australian
Chemical Institute


 

Article << Previous     |     Next >>   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

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 http://dx.doi.org/10.1071/CH11169
Submitted: 28 April 2011  Accepted: 24 May 2011   Published: 19 July 2011


 
PDF (1.1 MB) $25
 Export Citation
 Print
  
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 | CAS |
      (b) A. Pron, P. Gawrys, M. Zagorska, D. Djurado, R. Demadrille, Chem. Soc. Rev. 2010, 39, 2577.
         | CrossRef |
      (c) Y.-J. Cheng, S.-H. Yang, C.-S. Hsu, Chem. Rev. 2009, 109, 5868.
         | CrossRef |
      (d) A. R. Murphy, J. M. J. Fréchet, Chem. Rev. 2007, 107, 1066.
         | CrossRef |
      (e) M. Bendikov, F. Wudl, D. F. Perepichka, Chem. Rev. 2004, 104, 4891.
         | CrossRef |

[2]  (a) J. E. Anthony, Angew. Chem. Int. Ed. 2008, 47, 452.
         | CrossRef | CAS |
      (b) J. E. Anthony, Chem. Rev. 2006, 106, 5028.
         | CrossRef |

[3]  (a) N. Franz, G. Kreutzer, H.-A. Klok, Synlett 2006, , 1793.
         | CrossRef | CAS |
         (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 | CAS |

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

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

[7]  (a) K. Ito, T. Suzuki, Y. Sakamoto, D. Kubota, Y. Inoue, F. Sato, S. Tokito, Angew. Chem. Int. Ed. 2003, 42, 1159.
         | CrossRef | CAS |
      (b) W. Cui, X. Zhang, X. Jiang, H. Tian, D. Yan, Y. Geng, X. Jing, F. Wang, Org. Lett. 2006, 8, 785.
         | CrossRef |
      (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 |
      (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 |
      (e) S. Akiyama, S. Misumi, M. Nakagawa, Bull. Chem. Soc. Jpn. 1960, 33, 1293.
         | CrossRef |
      (f) W. Zhao, Q. Tang, H. S. Chan, J. Xu, K. Y. Lo, Q. Miao, Chem. Commun. 2008, , 4324.
         | CrossRef |
      (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 |
      (h) S. Toyota, M. Goichi, M. Kotani, Angew. Chem. Int. Ed. 2004, 43, 2248.
         | CrossRef |
      (i) S. Toyota, Chem. Lett. 2011, 40, 12.
         | CrossRef |
      (j) Y. Morisaki, T. Sawamura, T. Murakami, Y. Chujo, Org. Lett. 2010, 12, 3188.
         | CrossRef |

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

[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 |
      (c) A. M. Müller, Y. S. Avlasevich, K. Müllen, C. J. Bardeen, Chem. Phys. Lett. 2006, 421, 518.
         | CrossRef |
      (d) T. Kimoto, K. Tanaka, Y. Sakai, A. Ohno, K. Yoza, K. Kobayashi, Org. Lett. 2009, 11, 3658.
         | CrossRef |
      (e) V. S. Barlier, C. W. Schlenker, S. W. Chin, M. E. Thompson, Chem. Commun. 2011, 47, 3754.
         | CrossRef |

[10]  S. A. Odom, S. R. Parkin, J. E. Anthony, Org. Lett. 2003, 5, 4245.
         | CrossRef | CAS |

[11]  X. Zhang, X. Jiang, J. Luo, C. Chi, H. Chen, J. Wu, Chem. Eur. J. 2010, 16, 464.
         | CrossRef | CAS |

[12]  J. E. Anthony, J. S. Brooks, D. L. Eaton, S. R. Parkin, J. Am. Chem. Soc. 2001, 123, 9482.
         | CrossRef | CAS |

[13]  D. Lehnherr, J. Gao, F. A. Hegmann, R. R. Tykwinski, Org. Lett. 2008, 10, 4779.
         | CrossRef | CAS |

[14]  D. Lehnherr, A. H. Murray, R. McDonald, M. J. Ferguson, R. R. Tykwinski, Chem. Eur. J. 2009, 15, 12580.
         | CrossRef | CAS |

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

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

[17]  D. Lehnherr, A. H. Murray, R. McDonald, R. R. Tykwinski, Angew. Chem. Int. Ed. 2010, 49, 6190.
         | CrossRef | CAS |

[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 | CAS |
      (b) T. Vehoff, B. Baumeier, A. Troisi, D. Andrienko, J. Am. Chem. Soc. 2010, 132, 11702.
         | CrossRef |

[19]     (a) (a) For a selection of anthracene-based polymers, see: M. W. Pelter, J. K. Stille, Macromolecules 1990, 23, 2418. doi:10.1021/MA00211A002
      (b) P. Hodge, G. A. Power, M. A. Rabjohns, Chem. Commun. 1997, , 73.
         | CrossRef |
      (c) W. Cui, Y. Wu, H. Tian, Y. Geng, F. Wang, Chem. Commun. 2008, , 1017.
         | CrossRef |
      (d) W. Cui, Y. Zhao, H. Tian, Z. Xie, Y. Geng, F. Wang, Macromolecules 2009, 42, 8021.
         | CrossRef |
      (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 |
      (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 |
      (g) D. A. M. Egbe, B. Cornelia, J. Nowotny, W. Günther, E. Klemm, Macromolecules 2003, 36, 5459.
         | CrossRef |
      (h) M. S. Taylor, T. M. Swager, Angew. Chem. Int. Ed. 2007, 46, 8480.
         | CrossRef |
      (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 | CAS |

[21]  T. Okamoto, Y. Jiang, F. Qu, A. C. Mayer, J. E. Parmer, M. D. McGehee, Z. Bao, Macromolecules 2008, 41, 6977.
         | CrossRef | CAS |

[22]  G. P. Miller, J. Mack, Org. Lett. 2000, 2, 3979.
         | CrossRef | CAS |

[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 | CAS |

[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 | CAS |

[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 | CAS |

[26]  I. Osaka, T. Abe, S. Shinamura, K. Takimiya, J. Am. Chem. Soc. 2011, 133, 6852.
         | CrossRef | CAS |

[27]  S. Shinamura, I. Osaka, E. Miyazaki, A. Nakao, M. Yamagishi, J. Takeya, K. Takimiya, J. Am. Chem. Soc. 2011, 133, 5024.
         | CrossRef | CAS |

[28]  J. E. Anthony, J. Gierschner, C. A. Landis, S. R. Parkin, J. B. Sherman, R. C. Bakus, Chem. Commun. 2007, , 4746.
         | CrossRef | CAS |

[29]  For the initial report of compound 65, see: Payne M. M.Odom S. A.Parkin S. R.Anthony J. E.Org. Lett. 2004, 63325. 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 | CAS |

[31]  B. M. Medina, J. E. Anthony, J. Gieschner, ChemPhysChem 2008, 9, 1519.
         | CrossRef | CAS |


   
Subscriber Login
Username:
Password:  

 


    
Legal & Privacy | Contact Us | Help

CSIRO

© CSIRO 1996-2015