Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Synthesis of Dendrimer Containing Dialkylated-fluorene Unit as a Core Chromophore via Click Chemistry

  • Han, Seung-Choul (Department of Chemistry and Department of Medical Bioscience, Dong-A University) ;
  • Jin, Sung-Ho (Department of Chemistry Education, Pusan National University) ;
  • Lee, Jae-Wook (Department of Chemistry and Department of Medical Bioscience, Dong-A University)
  • Received : 2011.09.19
  • Accepted : 2011.11.11
  • Published : 2012.01.20
Download PDF
⟨ Previous Next ⟩

Abstract

The convergent synthetic strategy for the emissive dendrimers having the chromophore at core via the coppercatalyzed 1,3-dipolar cycloaddition reaction between alkyne and azide was described. 2,7-Diazido-9,9-dioctyl-9H-fluorene, designed to serve as the core in dendrimer, was stitched with the alkyne-functionalized Frechettype and PAMAM dendrons by the click chemistry leading to the formation of the corresponding fluorescent dendrimers in high yields. The preliminary photoluminescence studies indicated that 2,7-diazido-9,9-dioctyl-9H-fluorene showed no fluorescence due to the quenching effect from the electron-rich ${\alpha}$-nitrogen of the azido group but the dendrimers fluoresced due to the elimination of the quenching through the formation of the triazole ring.

Keywords

References

  1. Grimsdale, A. C.; Müllen, K. Angew. Chem. Int. Ed. 2005, 44, 5592. https://doi.org/10.1002/anie.200500805
  2. Tomalia, D. A. Prog. Polym. Sci. 2005, 30, 294. https://doi.org/10.1016/j.progpolymsci.2005.01.007
  3. Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem. Int. Ed. 2002, 41, 2596. https://doi.org/10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4
  4. Tornoe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057. https://doi.org/10.1021/jo011148j
  5. Wu, P.; Feldman, A. K.; Nugent, A. K.; Hawker, C. J.; Scheel, A.; Voit, B.; Pyun, J.; Fréchet, J. M. J.; Sharpless, K. B.; Fokin, V. V. Angew. Chem. Int. Ed. 2004, 43, 3928. https://doi.org/10.1002/anie.200454078
  6. Malkoch, M.; Schleicher, K.; Drockenmuller, E.; Hawker, C. J.; Russell, T. P.; Wu, P.; Fokin, V. V. Macromolecules 2005, 38, 3663. https://doi.org/10.1021/ma047657f
  7. Joralemon, M. J.; O'Reilly, R. K.; Matson, J. B.; Nugent, A. K.; Hawker, C. J.; Wooley, K. L. Macromolecules 2005, 38, 5436. https://doi.org/10.1021/ma050302r
  8. Franc, G.; Kakkar, A. Chem. Commun. 2008, 5267.
  9. Lee, J. W.; Kim, B. K. Bull. Korean Chem. Soc. 2005, 26, 658. https://doi.org/10.5012/bkcs.2005.26.4.658
  10. Lee, J. W.; Kim, B. K.; Jin, S. H. Bull. Korean Chem. Soc. 2005, 26, 833. https://doi.org/10.5012/bkcs.2005.26.5.833
  11. Lee, J. W.; Kim, B. K.; Kim, J. H.; Shin, W. S.; Jin, S. H. Bull. Korean Chem. Soc. 2005, 26, 1790. https://doi.org/10.5012/bkcs.2005.26.11.1790
  12. Lee, J. W.; Kim, B. K. Synthesis 2006, 615.
  13. Lee, J. W.; Kim, J. H.; Kim, B. K.; Shin, W. S.; Jin, S. H. Tetrahedron 2006, 62, 894. https://doi.org/10.1016/j.tet.2005.10.039
  14. Lee, J. W.; Kim, B. K.; Kim, H. J.; Han, S. C.; Shin, W. S.; Jin, S. H. Macromolecules 2006, 39, 2418. https://doi.org/10.1021/ma052526f
  15. Lee, J. W.; Kim, J. H.; Kim, B. K. Tetrahedron Lett. 2006, 47, 2683. https://doi.org/10.1016/j.tetlet.2006.02.081
  16. Lee, J. W.; Kim, B. K.; Kim, J. H.; Shin, W. S.; Jin, S. H. J. Org. Chem. 2006, 71, 4988. https://doi.org/10.1021/jo0605905
  17. Lee, J. W.; Kim, J. H.; Kim, B. K.; Kim, J. H.; Shin, W. S.; Jin, S. H. Tetrahedron 2006, 62, 9193. https://doi.org/10.1016/j.tet.2006.07.030
  18. Lee, J. W.; Kim, J. H.; Kim, B. K.; Kim, J. H.; Shin, W. S.; Jin, S. H.; Kim, M. Bull. Korean Chem. Soc. 2006, 27, 1795. https://doi.org/10.5012/bkcs.2006.27.11.1795
  19. Lee, J. W.; Kim, J. H.; Kim, H. J.; Han, S. C.; Kim, J. H.; Shin, W. S.; Jin, S. H. Bioconjugate Chem. 2007, 18, 579. https://doi.org/10.1021/bc060256f
  20. Lee, J. W.; Han, S. C.; Kim, J. H.; Ko, Y. H.; Kim, K. Bull. Korean Chem. Soc. 2007, 28, 1837. https://doi.org/10.5012/bkcs.2007.28.10.1837
  21. Lee, J. W.; Kim, H. J.; Han, S. C.; Kim, J. H.; Jin, S. H. J. Polym Sci. Part A: Polym. Chem. 2008, 46, 1083. https://doi.org/10.1002/pola.22451
  22. Lee, J. W.; Kim, H. J.; Han, S. C.; Kim, J. H.; Jin, S. H. J. Nanosci. Nanotechnol. 2008, 8, 4635. https://doi.org/10.1166/jnn.2008.IC59
  23. Lee, J. W.; Kim, B.-K.; Han, S. C.; Lee, U. Y.; Kim, J. H.; Oh, J.; Jin, S. H. Mol. Cryst. Liq. Cryst. 2008, 491, 164. https://doi.org/10.1080/15421400802329624
  24. Lee, J. W.; Kang, H.-S.; Han, S. C.; Sung, S. R.; Kim, J. H.; Oh, J.; Jin, S. H. Mol. Cryst. Liq. Cryst. 2008, 492, 139.
  25. Lee, J. W.; Lee, U. Y.; Han, S. C.; Kim, J. H.; Jin, S. H. Polymer (Korea) 2009, 33, 67.
  26. Lee, J. W.; Kim, B.-K.; Han, S. C.; Kim, J. H. Bull. Korean Chem. Soc. 2009, 30, 157. https://doi.org/10.5012/bkcs.2009.30.1.157
  27. Lee, J. W.; Han, S. C.; Kim, B.-K.; Lee, U. Y.; Sung, S. R.; Kang, H.-S.; Kim, J. H.; Jin, S. H. Macromol. Res. 2009, 17, 499. https://doi.org/10.1007/BF03218898
  28. Hawker, C. J.; Wooley, K. L. Science 2005, 309, 1200. https://doi.org/10.1126/science.1109778
  29. O'Reilly, R. K.; Joralemon, M. J.; Hawker, C. J.; Wooley, K. L. Chem. Eur. J. 2006, 12, 6776. https://doi.org/10.1002/chem.200600467
  30. Nandivada, H.; Chen, H.-Y.; Bondarenko, L.; Lahann, J. Angew. Chem. Int. Ed. 2006, 45, 3360. https://doi.org/10.1002/anie.200600357
  31. Moses, J. E.; Moorhouse, A. D. Chem. Soc. Rev. 2007, 36, 1249. https://doi.org/10.1039/b613014n
  32. Carlmark, A.; Hawker, C.; Hult, A.; Malkoch, M. Chem. Soc. Rev. 2009, 38, 352. https://doi.org/10.1039/b711745k
  33. Lu, G.; Lam, S.; Burgess, K. Chem. Commun. 2006, 1652.
  34. Laurent, B. A.; Grayson, S. M. J. Am. Chem. Soc. 2006, 128, 4238. https://doi.org/10.1021/ja0585836
  35. Ladmiral, V.; Mantovani, G.; Clarkson, G. J.; Cauet, S.; Irwin, J. L.; Haddleton, D. M. J. Am. Chem. Soc. 2006, 128, 4823. https://doi.org/10.1021/ja058364k
  36. Vogt, A. P.; Sumerlin, B. S. Macromolecules 2006, 39, 5286. https://doi.org/10.1021/ma0610461
  37. Karim, M. A.; Cho, Y.-R.; Park, J. S.; Kim, S. C.; Kim, H. J.; Lee, J. W.; Gal, Y.-S.; Jin, S. H. Chem. Commun. 2008, 1929.
  38. Fournier, D.; Hoogenboom, R.; Schubert, U. S. Chem. Soc. Rev. 2007, 36, 1369. https://doi.org/10.1039/b700809k
  39. Lutz, J.-F. Angew. Chem. Int. Ed. 2007, 46, 1018. https://doi.org/10.1002/anie.200604050
  40. Binder, W. H.; Sachsenhofer, R. Macromol. Rapid Commun. 2007, 28, 15. https://doi.org/10.1002/marc.200600625
  41. Hawker, C. J.; Fréchet, J. M. J. J. Am. Chem. Soc. 1990, 112, 7638. https://doi.org/10.1021/ja00177a027
  42. Grayson, S. M.; Fréchet, J. M. J. Chem. Rev. 2001, 101, 3819. https://doi.org/10.1021/cr990116h
  43. Bock, V. D.; Hiemstra, H.; van Maarseveen, J. H. Eur. J. Org. Chem. 2006, 51.
  44. Meldal, M.; Tornøe, C. W. Chem. Rev. 2008, 108, 2952. https://doi.org/10.1021/cr0783479
  45. Sivakumar, K.; Xie, F.; Cash, B. M.; Long, S.; Barnhill, H. N.; Wang, Q. Org. Lett. 2004, 6, 4603. https://doi.org/10.1021/ol047955x
  46. Mong, T. K.-K.; Niu, A.; Chow, H.-F.; Wu, C.; Li, L.; Chen, R. Chem. Eur. J. 2001, 7, 686. https://doi.org/10.1002/1521-3765(20010202)7:3<686::AID-CHEM686>3.0.CO;2-Z
  47. Wong, C.-H.; Chow, H.-F.; Hui, S.- K.; Sze, K.-H. Org. Lett. 2006, 8, 1811. https://doi.org/10.1021/ol0603716
  48. Sun, H.; Kaifer, A. E. Org. Lett. 2005, 7, 3845. https://doi.org/10.1021/ol051245p

Cited by

  1. Synthesis of Unsymmetrical Fréchet-type Dendrimers via Double Click Chemistry vol.33, pp.4, 2012, https://doi.org/10.5012/bkcs.2012.33.4.1393
  2. Convergent Synthesis of Carbazole Core PAMAM Dendrimer via Click Chemistry vol.34, pp.3, 2013, https://doi.org/10.5012/bkcs.2013.34.3.971
  3. Synthesis of Dendrimer Containing Carbazole Unit as a Core Chromophore vol.33, pp.10, 2012, https://doi.org/10.5012/bkcs.2012.33.10.3451
  4. Convergent Synthesis of PAMAM Dendrimers Containing Tetra(ethyleneoxide) at Core Using Click Chemistry vol.33, pp.10, 2012, https://doi.org/10.5012/bkcs.2012.33.10.3501
  5. Synthesis of Diblock Codendrimer by Double Click Chemistry vol.33, pp.12, 2012, https://doi.org/10.5012/bkcs.2012.33.12.4103
  6. Efficient Synthesis of Carbazole Core Diblock Dendrimer by Double Click Chemistry vol.599, pp.1, 2012, https://doi.org/10.1080/15421406.2014.935969
  7. Theoretical investigations into optical and charge transfer properties of donor-acceptor 1,8-naphthalimide derivatives as possible organic light-emitting materials vol.1103, pp.None, 2016, https://doi.org/10.1016/j.molstruc.2015.09.023