Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Facile Synthesis of Aldehyde-focal Fréchet Type Dendrons and Dendrimers via Staudinger/Aza-Wittig Reactions

  • 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 : 2011.08.01
  • Accepted : 2011.08.08
  • Published : 2011.10.20
Download PDF
⟨ Previous Next ⟩

Abstract

Fr$\acute{e}$chet-type dendritic benzaldehydes were efficiently synthesized using 3,5-dihydroxybenzaldehyde as an aldehyde focal point functionalized unit by adding a generation to the existing dendron or direct oxidation of Fr$\acute{e}$chet-type dendritic benzyl alcohols. These dendritic benzaldehydes were applied for the construction of dendrimers containing secondary amines as connectors via Staudinger/aza-Wittig Reactions with ${\alpha}$,${\alpha}'$,-diazidop-xylene core.

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. Newkome, G. R.; Moorefield, C. N.; Vogtle, F. Dendrimers and Dendrons: Concepts, Synthesis, Applications; Wiley-VCH: Weinheim, 2001.
  4. Fréchet, J. M. J.; Tomalia, D. A. Dendrimers and Other Dendritic Polymers; John Wiely & Sons Ltd., 2002.
  5. 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
  6. Tornøe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057. https://doi.org/10.1021/jo011148j
  7. Wu, P.; Feldman, A. K.; Nugent, A. K.; Hawker, C. J.; Scheel, A.; Voit, B.; Pyun, J.; Frechet, J. M. J.; Sharpless, K. B.; Fokin, V. V. Angew. Chem. Int. Ed. 2004, 43, 3928. https://doi.org/10.1002/anie.200454078
  8. 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
  9. 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
  10. Lee, J. W.; Kim, B. K. Bull. Korean Chem. Soc. 2005, 26, 658. https://doi.org/10.5012/bkcs.2005.26.4.658
  11. 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
  12. 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
  13. Lee, J. W.; Kim, B. K. Synthesis 2006, 615.
  14. 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
  15. 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
  16. Lee, J. W.; Kim, J. H.; Kim,B. K. Tetrahedron Lett. 2006, 47, 2683. https://doi.org/10.1016/j.tetlet.2006.02.081
  17. 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
  18. 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
  19. 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
  20. 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
  21. 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
  22. 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
  23. 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
  24. 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
  25. 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.
  26. Lee, J. W.; Lee, U. Y.; Han, S. C.; Kim, J. H.; Jin, S. H. Polymer (Korea) 2009, 33, 67.
  27. 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
  28. 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
  29. Helms, B.; Mynar, J. L.; Hawker, C. J.; Fréchet, J. M. J. J. Am. Chem. Soc. 2004, 126, 15020. https://doi.org/10.1021/ja044744e
  30. Mynar, J. L.; Choi, T.-L.; Yoshida, M.; Kim, V.; Hawker, C. J.; Fréchet, J. M. J. Chem. Commun. 2005, 5169.
  31. Hawker, C. J.; Wooley, K. L. Science 2005, 309, 1200. https://doi.org/10.1126/science.1109778
  32. 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
  33. Nandivada, H.; Chen, H.-Y.; Bondarenko, L.; Lahann, J. Angew. Chem. Int. Ed. 2006, 45, 3360. https://doi.org/10.1002/anie.200600357
  34. Moses, J. E.; Moorhouse, A. D. Chem. Soc. Rev. 2007, 36, 1249. https://doi.org/10.1039/b613014n
  35. Lee, J. W.; Lee, U. Y.; Han, S. C.; Kim, J. H. Bull. Korean Chem. Soc. 2009, 30, 1001. https://doi.org/10.5012/bkcs.2009.30.5.1001
  36. Grayson, S. M.; Fréchet, J. M. J. Chem. Rev. 2001, 101, 3919.
  37. Tozawa, T. Chem. Commun. 2004, 1904.
  38. Liao, L.-X.; Stellacci, F.; McGrath, D. V. J. Am. Chem. Soc. 2004, 126, 2181. https://doi.org/10.1021/ja036418p
  39. Hara, M.; Samori, S.; Cai, X.; Tojo, S.; Arai, T.; Momotake, A.; Hayakawa, J.; Uda, M.; Kawai, K.; Endo, M.; Fujitsuka, M.; Majima, T. J. Am. Chem. Soc. 2004, 126, 14217. https://doi.org/10.1021/ja046650a
  40. Diez-Barra, E.; Gonzalez, R.; Sanchez-Verdu, P.; Tolosa, J. Tetrahedron 2004, 60, 1563. https://doi.org/10.1016/j.tet.2003.12.003
  41. Momotake, A.; Arai, T. Tetrahedron Lett. 2004, 45, 4131. https://doi.org/10.1016/j.tetlet.2004.03.152
  42. Balzani, V.; Ceroni, P.; Giansante, C.; Vicinelli, V.; Klarner, F.-G.; Verhaelen, C.; Vogtle, F.; Hahn, U. Angew. Chem. Int. Ed. 2005, 44, 4574. https://doi.org/10.1002/anie.200501025
  43. Li, W.-S.; Jiang, D.-L.; Suna, Y.; Aida, T. J. Am. Chem. Soc. 2005, 127, 7700. https://doi.org/10.1021/ja0513335
  44. Shanahan, C. S.; McGrath, D. V. J. Org. Chem. 2005, 70, 1054. https://doi.org/10.1021/jo0483419
  45. Lee, J. W.; Kim, B. K.; Jin, S. H. Bull. Korean Chem. Soc. 2005, 26, 715. https://doi.org/10.5012/bkcs.2005.26.5.715
  46. Stewart, G. M.; Fox, M. A. J. Am. Chem. Soc. 1996, 118, 4354. https://doi.org/10.1021/ja954021i
  47. Fresneda, P. M.; Molina, P. Synlett 2004, 1.
  48. 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
  49. Wong, C.-H.; Chow, H.-F.; Hui, S.- K.; Sze, K.-H. Org. Lett. 2006, 8, 1811. https://doi.org/10.1021/ol0603716
  50. Sun, H.; Kaifer, A. E. Org. Lett. 2005, 7, 3845. https://doi.org/10.1021/ol051245p

Cited by

  1. Synthesis of dendrimers via Staudinger/aza-Wittig reaction of Fréchet-type dendritic benzyl azides and Fréchet-type dendritic benzaldehydes vol.20, pp.10, 2012, https://doi.org/10.1007/s13233-012-0149-4
  2. Synthesis of Fréchet-type Dendrimers with Tripodal Core via Staudinger/Aza-Wittig Reactions vol.38, pp.3, 2014, https://doi.org/10.7317/pk.2014.38.3.386
  3. Dendritic [2]Rotaxanes: Synthesis, Characterization, and Properties vol.79, pp.2, 2014, https://doi.org/10.1021/jo402428y