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RESEARCH ARTICLE
Contents Vol 68(1)

Synthesis, Photo-physical and Electrochemical Properties of Dendrimers with (S)-BINOL Core and Benzothiazole Surface Unit

Venkatesan Kalpana A , Kannan Rajavelu A and Perumal Rajakumar A B
+ Author Affiliations
- Author Affiliations

A Department of Organic Chemistry, University of Madras, Guindy Campus, Chennai-600 025, Tamilnadu, India.

B Corresponding author. Email: perumalrajakumar@gmail.com

Australian Journal of Chemistry 68(1) 93-98 https://doi.org/10.1071/CH13693
Submitted: 17 December 2013  Accepted: 27 March 2014   Published: 19 May 2014

Abstract

Chiral dendritic architectures with benzothiazole as surface group, 1,2,3-triazole as a bridging unit, and (S)-BINOL (1,1-bi-2-naphthol) as a core unit were synthesised in good yields via a convergent synthetic strategy. The chiroptical properties of the dendrimers revealed that the specific rotation increased in the order of dendrimers 4 > 3 > 2 > 1. All the dendrimers showed excellent optical and electrochemical response, and hence would find application in dye-sensitised solar cells.


References

[1]  Y. Cheng, L. Zhao, Y. Lic, T. Xu, Chem. Soc. Rev. 2011, 40, 2673.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXkvVWjtb0%3D&md5=8eedeab0f921be308b26a7951757fec1CAS | 21286593PubMed |

[2]  V. Balzani, P. Ceroni, S. Gesterman, C. Kauffmann, M. Gorka, F. Vogtle, Chem. Commun. 2000, 853.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3cXivFGqu78%3D&md5=2fe91545cdfce71b9240f9ed156a1130CAS |

[3]  (a) D. Guillon, R. Deschenaux, Curr. Opin. Solid State Mater. Sci. 2002, 6, 515.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXktVKgtb8%3D&md5=967a749b64817614db07422fd03fa7e9CAS |
      (b) B. Donnio, S. Buathong, I. Bury, D. Guillon, Chem. Soc. Rev. 2007, 36, 1495.
         | Crossref | GoogleScholarGoogle Scholar |

[4]  A. Adronov, J. M. J. Frechet, Chem. Commun. 2000, 1710.

[5]  J. Li, D. Liu, J. Mater. Chem. 2009, 19, 7584.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXht1Kjur%2FM&md5=35efff7aa9a43fe8898ef2fed4574916CAS |

[6]     (a) R. Huisgen, in 1,3-Dipolar Cycloaddition Chemistry (Ed. A. Padwa) 1984, Vol. 1, pp. 1–176 (Wiley: New York).
      (b) F. Himo, T. Lovell, R. Hilgraf, V. V. Rostovtsev, L. Noodleman, K. B. Sharpless, V. V. Fokin, J. Am. Chem. Soc. 2005, 127, 210.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) H. C. Kolb, M. G. Finn, K. B. Sharpless, Angew. Chem. Int. Ed. 2001, 40, 2004.
         | Crossref | GoogleScholarGoogle Scholar |

[7]  (a) C. W. Tornøe, C. Christensen, M. Meldal, J. Org. Chem. 2002, 67, 3057.
         | Crossref | GoogleScholarGoogle Scholar | 11975567PubMed |
      (b) V. V. Rostovtsev, L. G. Green, V. V. Fokin, K. B. Sharpless, Angew. Chem. Int. Ed. 2002, 41, 2596.
         | Crossref | GoogleScholarGoogle Scholar |

[8]  (a) O. David, S. Maisonneuvesss, J. Xie, Tetrahedron Lett. 2007, 48, 6527.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXpt1eqtrw%3D&md5=c61192bd250035d5f6fa38174e9e5982CAS |
      (b) K. Varazo, F. Xie, D. Gulledge, Q. Wang, Tetrahedron Lett. 2008, 49, 5293.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) P. D. Jarowski, Y. L. Wu, W. B. Schweizer, F. Diederich, Org. Lett. 2008, 10, 3347.
         | Crossref | GoogleScholarGoogle Scholar |

[9]  C. Wang, P. F. Ren, X. J. Huang, J. Wu, Z. K. Xu, Chem. Commun. 2011, 47, 3930.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXjt1Snur4%3D&md5=3fefefbda9d9823a7915ee0e8658230dCAS |

[10]  F. Yang, Y. Zhang, H. Guo, New J. Chem. 2013, 37, 2275.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhtFSisLfJ&md5=2d61e4bd6ca55dad0dd8572f73bd7760CAS |

[11]  (a) N. Siddiqui, S. K. Arya, W. Ahsan, B. Azad, Int. J. Drug Dev. Res 2011, 3, 156.
      (b) C. A. Mathis, Y. Wang, D. P. Holt, G. F. Huang, M. L. Debnath, W. E. Klunk, J. Med. Chem. 2003, 46, 2740.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) I. Hutchinson, A. S. Jenninga, B. R. Vishnuvajjala, A. D. Westwell, M. F. G. Stevens, J. Med. Chem. 2002, 45, 744.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) R. Caujolle, P. Loiseau, M. Payard, P. Gayral, Ann. Pharm. Fr. 1989, 47, 68.
      (e) K. Yamamoto, M. Fujita, K. Tabashi, Y. Kawashima, E. Kato, M. Oya, T. Iso, J. Iwao, J. Med. Chem. 1988, 31, 919.
         | Crossref | GoogleScholarGoogle Scholar |

[12]  (a) E. Díez-Barra, J. C. G. Martinez, R. D. Rey, J. R. Lopez, F. Giacalone, J. L. Segura, N. Martin, J. Org. Chem. 2003, 68, 3178.
         | Crossref | GoogleScholarGoogle Scholar | 12688788PubMed |
      (b) P. Gandhi, B. Huang, J. C. Gallucci, J. R. Parquette, Org. Lett. 2001, 3, 3129.
         | Crossref | GoogleScholarGoogle Scholar |

[13]  (a) G. H. Liu, Q. H. Fan, X. Q. Yang, X. M. Chen, ARKIVOC 2003, 2003, 123.
         | Crossref | GoogleScholarGoogle Scholar |
      (b) A. K. Bandyopadhyaya, N. M. Sangeetha, U. Maitra, J. Org. Chem. 2000, 65, 8239.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) L. Pu, Chem. Rev. 1998, 98, 2405.
         | Crossref | GoogleScholarGoogle Scholar |

[14]  P. Rajakumar, R. Anandhan, V. Kalpana, Synlett 2009, 1417.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXnslSmsb0%3D&md5=66bcfd6db3758c8647c8ab68c0acd9aeCAS |

[15]  P. Rajakumar, S. Raja, C. Satheeshkumar, S. Ganesan, P. Maruthamuthu, S. A. Suthanthiraraj, New J. Chem. 2010, 34, 2247.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXht1Wht7vJ&md5=0c4839b0dafa630cc63cab50f1e06fc2CAS |

[16]  P. Rajakumar, V. Kalpana, S. Ganesan, P. Maruthamuthu, Tetrahedron Lett. 2011, 52, 5812.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXht1Grur7I&md5=7580d6d90dc50b8d5e9bb72f369efa65CAS |

[17]  P. Rajakumar, V. Kalpana, S. Ganesan, P. Maruthamuthu, New J. Chem. 2013, 37, 3692.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhs1Wnt7nL&md5=a3af419295b380b38fb33601cd6d48ffCAS |

[18]  P. Rajakumar, R. Raja, Tetrahedron Lett. 2010, 51, 4365.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXptVagt7o%3D&md5=cfb7f010359659e0c2c6d772e81879c8CAS |

[19]  S. Galeazzi, T. M. Hermans, M. Paolino, M. Anzini, L. Mennuni, A. Giordani, G. Caselli, F. Makovee, E. W. Meijer, S. Vomero, A. Cappelli, Biomacromolcules 2010, 11, 182.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXhsFSrsbnF&md5=d0139ed8e2f71e84d7b21b7e50cf4c9cCAS |

[20]  (a) S. Roffia, G. Feroci, J. Electroanal. Chem. 1978, 88, 169.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE1cXhs1Slur4%3D&md5=99f65d905cd0fc2c4591f16c1aa5c15eCAS |
      (b) J. A. Osaheni, S. A. Jenekhe, Chem. Mater. 1995, 7, 672.
         | Crossref | GoogleScholarGoogle Scholar |