Display options
Share it on

Beilstein J Org Chem. 2014 Dec 22;10:3097-103. doi: 10.3762/bjoc.10.326. eCollection 2014.

Redox active dendronized polystyrenes equipped with peripheral triarylamines.

Beilstein journal of organic chemistry

Toshiki Nokami, Naoki Musya, Tatsuya Morofuji, Keiji Takeda, Masahiro Takumi, Akihiro Shimizu, Jun-Ichi Yoshida

Affiliations

  1. Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto 615-8510, Japan.

PMID: 25670978 PMCID: PMC4311719 DOI: 10.3762/bjoc.10.326

Abstract

Dendronized polystyrene having peripheral bromo groups was prepared from the dendronization of unfunctionalized polystyrene with dendritic diarylcarbenium ions bearing peripheral bromo groups using the "cation pool" method. The palladium-catalyzed amination of the peripheral bromo groups with diarylamine gave dendronized polystyrene equipped with peripheral triarylamines, which exhibited two sets of reversible redox peaks in the cyclic voltammetry curves.

Keywords: carbocation; cross-coupling; dendrimer; dendronized polymer; redox

References

  1. J Am Chem Soc. 2011 Aug 10;133(31):11840-3 - PubMed
  2. J Am Chem Soc. 2008 Aug 20;130(33):10864-5 - PubMed
  3. J Am Chem Soc. 2004 Nov 17;126(45):14702-3 - PubMed
  4. Angew Chem Int Ed Engl. 1998 Dec 31;37(24):3387-3388 - PubMed
  5. J Am Chem Soc. 2002 Dec 18;124(50):14824-5 - PubMed
  6. Chemistry. 2002 Jun 17;8(12):2651-8 - PubMed
  7. Nat Biotechnol. 2005 Dec;23(12):1517-26 - PubMed
  8. Angew Chem Int Ed Engl. 2009;48(17):3141-5 - PubMed
  9. J Am Chem Soc. 2005 Aug 24;127(33):11666-75 - PubMed
  10. J Am Chem Soc. 2013 Oct 30;135(43):16070-3 - PubMed
  11. Chem Rev. 2009 Nov;109(11):6275-540 - PubMed
  12. Nat Chem. 2012 Mar 22;4(4):255-67 - PubMed
  13. Org Biomol Chem. 2013 May 28;11(20):3322-31 - PubMed
  14. J Am Chem Soc. 2002 Jun 12;124(23):6520-1 - PubMed
  15. Angew Chem Int Ed Engl. 2001 Jan 5;40(1):224-227 - PubMed
  16. J Am Chem Soc. 2004 Nov 10;126(44):14338-9 - PubMed
  17. Chem Commun (Camb). 2011 May 21;47(19):5575-7 - PubMed
  18. Acc Chem Res. 2008 Dec;41(12):1641-52 - PubMed
  19. Org Lett. 2012 Feb 3;14(3):938-41 - PubMed
  20. Org Lett. 2006 Oct 26;8(22):5005-7 - PubMed
  21. J Am Chem Soc. 2005 May 25;127(20):7324-5 - PubMed
  22. J Am Chem Soc. 2007 Feb 21;129(7):1902-3 - PubMed
  23. J Am Chem Soc. 2005 May 18;127(19):6930-1 - PubMed
  24. Org Lett. 2009 Feb 19;11(4):975-8 - PubMed
  25. Chem Rev. 2001 Dec;101(12):3819-68 - PubMed
  26. Angew Chem Int Ed Engl. 2000 Mar;39(5):864-883 - PubMed
  27. J Am Chem Soc. 2001 Aug 15;123(32):7941-2 - PubMed
  28. J Am Chem Soc. 2006 Jun 21;128(24):7710-1 - PubMed
  29. Chem Commun (Camb). 2002 Dec 21;(24):2950-1 - PubMed
  30. J Am Chem Soc. 2011 Jan 26;133(3):629-41 - PubMed

Publication Types