DOI QR코드

DOI QR Code

Synthesis of Dendrimers from Alkyne-focal Dendrons by Oxidative Homo-coupling of Terminal Acetylene

  • Received : 2011.07.31
  • Accepted : 2011.09.05
  • Published : 2011.11.20

Abstract

General, fast, and efficient fusion methods for the synthesis of dendrimers with 1,3-diynes at a core were developed. The synthetic strategy was employed the oxidative homo-coupling of terminal alkyne. The oxidative homo-coupling reaction of the alkyne-functionalized Frechet-type dendrons 1-Dm was allowed to provide first through fourth generation dendrimers 2-Gm with 1,3-diynes at core. The fusion of the propargylfunctionalized PAMAM dendrons 3-Dm by homo-coupling of terminal alkyne lead to the formation of symmetric PAMAM dendrimers 4-Gm. Their structure of dendrimers was confirmed by $^1H$ and $^{13}C$ NMR spectroscopy, IR spectroscopy, mass spectrometry, and GPC analysis.

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.; F. Vogtle, Dendrimers and Dendrons: Concepts, Synthesis, Applications; Wiley-VCH: Weinheim, 2001.
  4. Frechet, 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. Tornoe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057. https://doi.org/10.1021/jo011148j
  7. Lee, J. W.; Kim, B. K. Bull. Korean Chem. Soc. 2005, 26, 658. https://doi.org/10.5012/bkcs.2005.26.4.658
  8. 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
  9. 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
  10. Lee, J. W.; Kim, B. K. Synthesis 2006, 615.
  11. 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
  12. 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
  13. Lee, J. W.; Kim, J. H.; Kim, B. K. Tetrahedron Lett. 2006, 47, 2683. https://doi.org/10.1016/j.tetlet.2006.02.081
  14. 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
  15. 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
  16. 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
  17. 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
  18. 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
  19. 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
  20. 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
  21. 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
  22. 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.
  23. Lee, J. W.; Lee, U. Y.; Han, S. C.; Kim, J. H.; Jin, S. H. Polymer (Korea) 2009, 33, 67.
  24. 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
  25. 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
  26. Negishi, E.; Anastasia, L. Chem. Rev. 2003, 103, 1979. https://doi.org/10.1021/cr020377i
  27. Zhang, W.; Moore, J. S. Angew. Chem. Int. Ed. 2006, 45, 4416. https://doi.org/10.1002/anie.200503988
  28. Siemsen, P.; Livingston, R. C.; Diederich, F. Angew. Chem. Int. Ed. 2000, 39, 2632. https://doi.org/10.1002/1521-3773(20000804)39:15<2632::AID-ANIE2632>3.0.CO;2-F
  29. Moreno-Manas, M.; Pleixats, R. Acc. Chem. Res. 2003, 36, 638. https://doi.org/10.1021/ar020267y
  30. Dieck, H. A.; Heck, R. F. J. Organomet. Chem. 1975, 93, 259. https://doi.org/10.1016/S0022-328X(00)94049-X
  31. Cassar, I. J. Organomet. Chem. 1975, 93, 253. https://doi.org/10.1016/S0022-328X(00)94048-8
  32. Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 16, 4467. https://doi.org/10.1016/S0040-4039(00)91094-3
  33. Bunz, U. H. F. Chem. Rev. 2000, 100, 1605. https://doi.org/10.1021/cr990257j
  34. Chinchilla, R.; Najera, C. Chem. Rev. 2007, 107, 874. https://doi.org/10.1021/cr050992x
  35. Lee, J. W.; Han, S. C.; Lee, U. Y.; Kim, B.-K.; Kim, J. H. Bull. Korean Chem. Soc. 2009, 30, 1925. https://doi.org/10.5012/bkcs.2009.30.9.1925
  36. 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
  37. Wong, C.-H.; Chow, H.-F.; Hui, S.- K.; Sze, K.-H. Org. Lett. 2006, 8, 1811. https://doi.org/10.1021/ol0603716
  38. Sun, H.; Kaifer, A. E. Org. Lett. 2005, 7, 3845. https://doi.org/10.1021/ol051398c

Cited by

  1. Synthesis of Fréchet-type Dendrimer Using Glaser-type Coupling Reaction of the Terminal Alkyne-focal Dendrons vol.597, pp.1, 2011, https://doi.org/10.1080/15421406.2014.932233
  2. Efficient polymer dimerization method based on self-accelerating click reaction vol.10, pp.12, 2020, https://doi.org/10.1039/c9ra09919k
  3. Synthesis of Chromophore Core Fréchet-Type Dendrimer by Oxidative Homo-Coupling of Terminal Alkyne vol.29, pp.6, 2011, https://doi.org/10.1007/s13233-021-9051-2