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

1,2,3-Triazole Ferrocenyldendrimers Through Click Chemistry Approach and their Optical and Electrochemical Properties

Perumal Rajakumar A B , Ramasamy Anandhan A and Ayyavoo Kannan A
+ Author Affiliations
- Author Affiliations

A Department of Organic Chemistry, University of Madras, Maraimalai Campus, Chennai 600 025, India.

B Corresponding author. Email: perumalrajakumar@gmail.com

Australian Journal of Chemistry 65(10) 1457-1462 https://doi.org/10.1071/CH12166
Submitted: 23 March 2012  Accepted: 8 August 2012   Published: 14 September 2012

Abstract

Novel ferrocenyl dendrimers with ferrocene as a surface group and with triazole as a bridging unit have been synthesised through click chemistry. The increasing numbers of triazole and ferrocenyl units at the antenna increase the light absorbing ability. The electrochemical behaviour changes with increasing ferrocenyl and triazole units.


References

[1]  (a) J. F. Lutz, Angew. Chem. Int. Ed. 2007, 46, 1018.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXitVKgsrc%3D&md5=8ca3b430cb63699cc8779645bc2c2f26CAS |
      (b) J. E. Moses, A. D. Moorhouse, Chem. Soc. Rev. 2007, 36, 1249.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) J. F. Lutz, Z. Zarafshani, Adv. Drug Deliv. Rev. 2008, 60, 958.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) A. D. Moorhouse, J. E. Moses, ChemMedChem 2008, 3, 715.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) G. C. Tron, T. Pirali, R. A. Billington, P. L. Canonico, G. Sorba, A. A. Genazzani, Med. Res. Rev. 2008, 28, 278.
         | Crossref | GoogleScholarGoogle Scholar |

[2]  QSAR Comb. Sci. 2007, 26 (11) is a special issue on click chemistry and its applications.

[3]  (a) M. Meldal, C. W. Tornøe, Chem. Rev. 2008, 108, 2952.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXps1yhurk%3D&md5=f3e0bea30fa088229b1cbb252121a7e0CAS |
      (b) W. H. Binder, R. Sachsenhofe, Macromol. Rapid Commun. 2007, 28, 15.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) B. Dervaux, F. E. Du Prez, Chem. Sci. 2012, 3, 959.
         | Crossref | GoogleScholarGoogle Scholar |

[4]  (a) H. C. Kolb, M. G. Finn, K. B. Sharpless, Angew. Chem. Int. Ed. 2001, 40, 2004.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXksVOis78%3D&md5=af962a1dfdc14748785758477eb28f57CAS |
      (b) P. Appukkuttan, W. Dehaen, V. V. Fokin, E. V. Eycken, Org. Lett. 2004, 6, 4223.
         | Crossref | GoogleScholarGoogle Scholar |

[5]  (a) N. Akeroyd, B. Klumperman, Eur. Polym. J. 2011, 47, 1207.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXmtFarsLY%3D&md5=70a0de883f0f71f5e8c66806d7b77e49CAS |
      (b) C. D. Hein, X. M. Liu, D. Wang, Pharm. Res. 2008, 25, 2216.
         | Crossref | GoogleScholarGoogle Scholar |

[6]  Y. Naito, F. Akahoshi, S. Takeda, T. Okada, M. Kajii, H. Nishimura, M. Sugiura, C. Fukaya, Y. Kagitani, J. Med. Chem. 1996, 39, 3019.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK28XjvVartb0%3D&md5=8f33a3f14cde2fac654617f236ce55abCAS |

[7]  O. Makabe, H. Suzuki, S. Umezawa, Bull. Chem. Soc. Jpn. 1977, 50, 2689.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE1cXitlejtw%3D%3D&md5=9b74d667c19ec7dfcac257e426a07e6eCAS |

[8]  M. J. Genin, D. A. Allwine, D. J. Anderson, M. R. Barbachyn, D. E. Emmert, S. A. Garmon, D. R. Graber, K. C. Grega, J. B. Hester, D. K. Hutchinson, J. Morris, R. D. Reischer, D. Stper, B. H. Yagi, J. Med. Chem. 2000, 43, 953.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3cXhtFWrt78%3D&md5=b360cea3c04223c9cca65c3f4ef1efd9CAS |

[9]  R. Alvarez, S. Velazquez, A. San-Felix, S. Aquaro, E. Declercq, C. F. Perno, A. Karlsson, J. Balzarini, M. J. Camarasa, J. Med. Chem. 1994, 37, 4185.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2MXhvFKmsbw%3D&md5=a9b44ceb47893c8a9e1239e5e5104f93CAS |

[10]  D. R. Buckle, C. J. M. Rockell, H. Smith, B. A. Spicer, J. Med. Chem. 1986, 29, 2262.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL28Xmt1Knu7w%3D&md5=345adb7dcfcdf1680cef4e1973221facCAS |

[11]  (a) D. Astruc, New J. Chem. 2011, 35, 764.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXktVSjt78%3D&md5=5840aefcd265ddb0d63bfe272d8e84edCAS |
      (b) C. M. Casado, I. Cuadrado, M. Moran, B. Alonso, B. Garcia, B. Gonzales, J. Losada, Coord. Chem. Rev. 1999, 185–186, 53.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) D. Astruc, C. Ornelas, J. Ruiz, Acc. Chem. Res. 2008, 41, 841.
         | Crossref | GoogleScholarGoogle Scholar |

[12]  (a) M. P. G. Armada, J. Losada, M. Zamora, B. Alonso, I. Cuadrado, C. M. Casado, Bioelectrochemistry 2006, 69, 65.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28Xosl2qtb0%3D&md5=d0eb1c14ed61934c5947bc7cd6b06672CAS |
      (b) J. Losada, M. Zamora, P. G. Armada, I. Cuadrado, B. Alonso, C. M. Casado, Anal. Bioanal. Chem. 2006, 385, 1209.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) F. J. Martinez, B. Gonzalez, B. Alonso, J. Losada, M. P. Garcia-Armada, C. M. Casado, J. Inorg. Organomet. P. 2008, 18, 51.
         | Crossref | GoogleScholarGoogle Scholar |

[13]  M. C. Daniel, J. Ruiz, D. Astruc, J. Am. Chem. Soc. 2003, 125, 1150.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXitVOkug%3D%3D&md5=939595fe49c98d6bc57ed08b66c7e25fCAS |

[14]  C. Ornelas, J. Ruiz, C. Belin, D. Astruc, J. Am. Chem. Soc. 2009, 131, 590.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXmsVCg&md5=d36bffd20fae8b9199ecde6206f1d41aCAS |

[15]  (a) P. Nguyen, P. Gomez-Elipe, I. Manners, Chem. Rev. 1999, 99, 1515.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXislyju70%3D&md5=b53a1fd7b1339480cf6940b0b1e58f0eCAS |
      (b) R. Rulkens, A. J. Lough, I. Manners, S. R. Lovelace, C. Grant, W. E. Geiger, J. Am. Chem. Soc. 1996, 118, 12683.
         | Crossref | GoogleScholarGoogle Scholar |

[16]  (a) C. Ornelas, J. R. Aranzaes, E. Cloutet, S. Alves, D. Astruc, Angew. Chem. Int. Ed. 2007, 46, 872.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXhs1aqt74%3D&md5=2416b3b3a2cf6228d6945854db344716CAS |
      (b) R. Djeda, A. Rapakousiou, L. Liang, N. Guidolin, J. Ruiz, D. Astruc, Angew. Chem. 2010, 122, 8328.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) D. Astruc, L. Liang, A. Rapakousiou, J. Ruiz, Acc. Chem. Res. 2012, 45, 630.
         | Crossref | GoogleScholarGoogle Scholar |

[17]  (a) M. C. Daniel, J. Ruiz, J. C. Blais, N. Daro, D. Astruc, Chem. – Eur. J. 2003, 9, 4371.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXnvVygt7c%3D&md5=07d43dcf6b2bf28cde1d4d24b266b14eCAS |
      (b) D. G. MacDonald, C. Kubel, J. F. Corrigan, Inorg. Chem. 2011, 50, 3252.
         | Crossref | GoogleScholarGoogle Scholar |

[18]  (a) C. Ornelas, L. Salmon, J. Ruiz, D. Astruc, Chem. – Eur. J. 2008, 14, 50.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXltVarsLc%3D&md5=235048483afcd78327bbaeb21b3eb670CAS |
      (b) E. Boisselier, A. K. Diallo, L. Salmon, C. Ornelas, J. Ruiz, D. Astruc, J. Am. Chem. Soc. 2010, 132, 2729.
         | Crossref | GoogleScholarGoogle Scholar |

[19]  (a) P. Rajakumar, R. Anandhan, V. Kalpana, Synlett 2009, 2009, 1417.
         | Crossref | GoogleScholarGoogle Scholar |
      (b) P. Rajakumar, R. Anandhan, Eur. J. Med. Chem. 2011, 46, 4687.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) P. Rajakumar, C. Satheeshkumar, S. Raja, Tetrahedron Lett. 2010, 51, 5167.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) P. Rajakumar, R. Raja, Tetrahedron Lett. 2010, 51, 4365.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) P. Rajakumar, V. Kalpana, S. Ganesan, P. Maruthamuthu, Tetrahedron Lett. 2011, 52, 5812.
         | Crossref | GoogleScholarGoogle Scholar |
      (f) P. Rajakumar, A. Thirunarayanan, S. Raja, S. Ganesan, P. Maruthamuthu, Tetrahedron Lett. 2012, 53, 1139.
         | Crossref | GoogleScholarGoogle Scholar |

[20]  (a) P. Rajakumar, S. Raja, S. Ganesan, P. Maruthamuthu, S. A. Suthanthiraraj, New J. Chem. 2010, 34, 2247.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXht1Wht7vJ&md5=c9ead74ce0fb4e3bfefda0baf91902d3CAS |
      (b) S. Raja, C. Satheeshkumar, P. Rajakumar, S. Ganesan, P. Maruthamuthu, J. Mater. Chem. 2011, 21, 7700.
         | Crossref | GoogleScholarGoogle Scholar |