DOI QR코드

DOI QR Code

Novel Synthesis of Hydrophilic Dipolar Chromophores using Dendronized Sulfonates

  • Kim, Mi-Rae (Department of Advanced Materials for Information and Display Devices, Pusan National University) ;
  • Maheswara, Muchchintala (Department of Advanced Materials for Information and Display Devices, Pusan National University) ;
  • Do, Jung-Yun (Department of Advanced Materials for Information and Display Devices, Pusan National University)
  • Received : 2010.12.22
  • Accepted : 2011.01.17
  • Published : 2011.02.20

Abstract

A series of hydrophilic chromophores was synthesized through introduction of dendritic sulfonate anions using click chemistry. A dendron structure bearing several sulfonate groups enhances hydrophilicity of attached chromophores. A click triazole formation connects chromophores with hydrophilic groups. A neutral trichloroethyl sulfonate has versatile features such as easy introduction, chemical endurance for isolation or storage, and convenient transformation to a hydrophilic anion. Zinc and OH mediated cleavage of trichloroethyl group from the neutral sulfonate undergoes to generate a water-soluble sulfonate anion. The solubility was examined with different counter cations and in different pH media and thus increased with the number of attached sulfonate ion. Two hydrophilic chromophores of stilbene-derived and azobenzene-derived dipolar structures exhibit clear negative and positive solvatochromism in protic solvents, respectively.

Keywords

References

  1. Frechet, J. M. J.; Tomalia, D. A. Dendrimers and other Dendritic Polymers; Wiley: New York, 2001.
  2. Weil, T.; Wiesler, U. M.; Herrmann, A.; Bauer, R.; Hofkens, J.; Schryver, F. C. D.; Mu1llen, K. J. Am. Chem. Soc. 2001, 123, 8101-8108. https://doi.org/10.1021/ja010579g
  3. Dichtel, W. R.; Hecht, S.; Frechet, J. M. J. Org. Lett. 2005, 7(20), 4451-4454. https://doi.org/10.1021/ol0516824
  4. Tully, D. C.; Frechet, J. M. J. Chem. Commun. 2001, 14, 1229-1239.
  5. Aida, T.; Jiang, D. L. Dendrimer Porphyrins and Metalloporphyrins: Syntheses, Structure, and Functions; In Kadish, K. M., Smith, K. M., Guilard, R., Eds.; The Porphyrin Handbook Inorganic, Organometallic, and Coordination Chemistry, Vol. 3. Academic Press: New York, 2000; pp 369-384.
  6. Zeng, F.; Zimmerman, S. C. Chem. Rev. 1997, 97, 1681-1712. https://doi.org/10.1021/cr9603892
  7. Bosman, A. W.; Janssen, H. M.; Meijer, E. W. Chem. Rev. 1999, 99, 1665-1688. https://doi.org/10.1021/cr970069y
  8. Inoue, K. Prog. Polym. Sci. 2000, 25, 453-571. https://doi.org/10.1016/S0079-6700(00)00011-3
  9. Vogtle, F.; Gestermann, S.; Hesse, R.; Schwierz, H.; Windisch, B. Prog. Polym. Sci. 2000, 25, 987-1041. https://doi.org/10.1016/S0079-6700(00)00017-4
  10. Frauenrath, H. Prog. Polym. Sci. 2005, 30, 325-384. https://doi.org/10.1016/j.progpolymsci.2005.01.011
  11. Haibo, X.; Hui, L.; Minjuan, C.; Lei, W. Dyes and Pigments 2009, 83, 334-338. https://doi.org/10.1016/j.dyepig.2009.05.012
  12. Krishna, T. R.; Parent, M.; Werts, M. H. V.; Moreaux, L.; Gmouh, S.; Charpak, S.; Caminade, A. M.; Majoral, J. P.; Desce, M. B. Angew. Chem. Int. Ed. 2006, 45, 4645-4648. https://doi.org/10.1002/anie.200601246
  13. Wang, S.; Gaylord, B. S.; Bazan, G. C. Adv. Mater. 2004, 16, 2127-2132. https://doi.org/10.1002/adma.200401036
  14. Ahmeda, S. M.; Budda, P. M.; Mckeowna, N. B.; Evansb, K. P.; Beaumontb, G. L.; Donaldsonc, C.; Brennanc, C. M. Polymer 2001, 42, 889-896. https://doi.org/10.1016/S0032-3861(00)00483-3
  15. Catalina, F.; Peinado, C.; Blanco, M.; Allen, N. S.; Corrales, T.; Lukac, I. Polymer 1998, 39, 4399-4408. https://doi.org/10.1016/S0032-3861(97)10175-6
  16. Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 40, 2004-2021. https://doi.org/10.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.0.CO;2-5
  17. Tornoe, C. M.; Christensen, C.; Maldal, M. J. J. Org. Chem. 2002, 67, 3057-3064. https://doi.org/10.1021/jo011148j
  18. Subbaraman, R.; Ghassemi, H.; Zawodzinski, T. A. J. Am. Chem. Soc. 2007, 129, 2238-2239. https://doi.org/10.1021/ja067332+
  19. Martwiseta, S.; Woudenberga, R. C.; Granados-Focila, S.; Yavuzcetinb, O.; Yuominenb, M. T.; Coughlin, E. B. Solid State Ionics 2007, 178, 1398-1403. https://doi.org/10.1016/j.ssi.2007.07.005
  20. Rajukumar, P.; Raja, R. Tetrahedron Lett. 2001, 51, 4365-4370.
  21. Chanthateyanonth, R.; Ruchirawat, S.; Srisitthiratku, C. Journal of Applied Polymer Science 2010, 116, 2074-2082.
  22. Miller, S. C. J. Org. Chem. 2010, 75, 4632-4635. https://doi.org/10.1021/jo1007338
  23. Ali, A. M.; Hill, B.; Taylor, S. D. J. Org. Chem. 2009, 74, 3583-3586. https://doi.org/10.1021/jo900122c
  24. Somsak, L.; Czifrak, K.; Veres, E. Tetrahedron Lett. 2004, 45, 9095-9097. https://doi.org/10.1016/j.tetlet.2004.10.026
  25. Liu, Y.; Lien, I. F. F.; Ruttgaizer, S.; Dove, P.; Taylor, S. D. Org. Lett. 2004, 6, 209-212. https://doi.org/10.1021/ol036157o
  26. Park, K. H.; Twieg, R. J.; Ravikiran, R.; Rhodes, L. F.; Shick, R. A.; Yankelevich, D.; Knoesen, A. Macromolecules 2004, 37, 5163-5178. https://doi.org/10.1021/ma040044i
  27. Kim, H. K.; Moon, I. K.; Lee, H. J.; Han, S. G.; Won, Y. H. Polymer 1998, 39, 1719-1726. https://doi.org/10.1016/S0032-3861(97)00459-X
  28. Robello, D. R.; Dao, P. T.; Schildkraut J. S.; Scozzafava, M.; Urankar, E. J.; Wiland, Chem. Mater. 1995, 7, 284-291. https://doi.org/10.1021/cm00050a009
  29. Abe, J.; Shirai, Y. J. Am. Chem. Soc. 1996, 118, 4705-4706. https://doi.org/10.1021/ja9535017
  30. Airinei, A.; Homocianu, M.; Dorohoi, D. O. J. Mol. Liq. 2010, 157, 13-17. https://doi.org/10.1016/j.molliq.2010.07.011

Cited by

  1. ChemInform Abstract: Novel Synthesis of Hydrophilic Dipolar Chromophores Using Dendronized Sulfonates. vol.42, pp.24, 2011, https://doi.org/10.1002/chin.201124129