Spherical polyphenylene dendrimers via Diels–Alder reactions: the first example of an A4B building block in dendrimer chemistry

(Note: The full text of this document is currently only available in the PDF Version )

Frank Morgenroth


Abstract

The [2+4]cycloaddition of the novel A4B building block 2,3,4,5-tetrakis(4-triisopropylsilylethynylphenyl)cyclopenta-2,4-dienone 3 with 3,3’,5,5’-tetraethynylbiphenyl 1 allows the rapid synthesis of a spherical polyphenylene nanoparticle with 102 benzene rings.


References

  1. G. R. Newkome, C. N. Moorefield and F. Vögtle, Dendritic Molecules, VCH Verlag, Weinheim, 1996 Search PubMed.
  2. J. M. J. Fréchet and C. J. Hawker, in Comprehensive Polymer Science, 2. Supl., ed. G. Allen, S. L. Aggarwal and S. Russo, Elsevier, Oxford, 1996, S. 70–129 Search PubMed.
  3. F. Morgenroth, E. Reuther and K. Müllen, Angew. Chem., 1997, 109, 647 CrossRef; Angew. Chem., Int. Ed. Engl., 1997, 36, 631 Search PubMed.
  4. F. Morgenroth, C. Kübel and K. Müllen, J. Mater. Chem., 1997, 7, 1207 RSC.
  5. It ought to be mentioned in this context that Fréchet and Otha have recently described the synthesis of an end-reactive AB4 dendron (made from two different AB2 building blocks) for the accelerated synthesis of dendritic polymers: M. Ohta and J. M. J. Fréchet, J. Macromol. Sci., Pure Appl. Chem., 1997, A34, 2025 Search PubMed.
  6. F. Morgenroth and K. Müllen, Tetrahedron, 1997, 53, 15 349 CrossRef CAS and references cited therein.
  7. S. Takahashi, Y. Kuroyama, K. Sonogashira and N. Hagihara, Synthesis, 1980, 627 CrossRef CAS.
  8. CERIUS2, Molecular Simulations Inc., Waltham, MA, USA. For more details see ref. 4. Additional data are to be published.
  9. M. Maciejewski, J. Macromol. Sci. Chem., 1982, A17, 689 Search PubMed.
  10. P.-G. de Gennes and H. Hervet, J. Phys. Lett., 1983, 44, L-351 Search PubMed.
  11. D. A. Tomalia and H. D. Durst, Top. Curr. Chem., 1993, 165, 193 CAS.
  12. T. M. Miller, T. X. Neenan, R. Zayas and H. E. Bair, J. Am. Chem. Soc., 1992, 114, 1018 CrossRef CAS.
  13. Y. H. Kim and O. W. Webster, J. Am. Chem. Soc., 1990, 112, 4592 CrossRef CAS.
Click here to see how this site uses Cookies. View our privacy policy here.