View PDF Version
 
DOI: 10.1039/A801269E (Paper) Reference Section for: Chem. Commun., 1998, 1013-1014

Dendritic rods with a poly(triacetylene) backbone: insulated molecular wires

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

Albertus P. H. J. Schenning, Rainer E. Martin, Masato Ito, François Diederich, Albertus P. H. J. Schenning, Rainer E. Martin, Corinne Boudon, Jean-Paul Gisselbrecht and Maurice Gross

Abstract

Multinanometer long phenylacetylene-end-capped poly(triacetylene) (PTA) oligomers with dendritic side chains of generation one to three have been prepared; UV–VIS measurements indicate that there is no loss of π-electron conjugation along the PTA backbone in the higher generation compounds despite distortion from planarity due to the bulky dendritic wedges.

References

  1. (a) J. Anthony, C. Boudon, F. Diederich, J.-P. Gisselbrecht, V. Gramlich, M. Gross, M. Hobi and P. Seiler, Angew. Chem., Int. Ed. Engl., 1994, 33, 763 CrossRef ; (b) R. E. Martin, U. Gubler, C. Boudon, V. Gramlich, C. Bosshard, J.-P. Gisselbrecht, P. Günter, M. Gross and F. Diederich, Chem. Eur. J., 1997, 3, 1505 CrossRef CAS .
  2. J.-F. Nierengarten, D. Guillon, B. Heinrich and J.-F. Nicoud, Chem. Commun., 1997, 1233 RSC .
  3. G. R. Newkome, C. N. Moorefield and F. Vögtle, Dendritic Molecules: Concepts, Synthesis, Perspectives, VCH, Weinheim, New York, 1996 Search PubMed ; D. A. Tomalia, A. M. Naylor and W. A. Goddard, Angew. Chem., Int. Ed. Engl., 1990, 29, 138 Search PubMed ; J. M. J. Fréchet, Science, 1994, 263, 1710 CrossRef .
  4. R. Klopsch, P. Franke and A.-D. Schlüter, Chem. Eur. J., 1996, 2, 1330 CAS ; B. Karakaya, W. Claussen, K. Gessler, W. Saenger and A.-D. Schlüter, J. Am. Chem. Soc., 1997, 119, 3296 CrossRef CAS .
  5. C. J. Hawker and J. M. J. Fréchet, J. Chem. Soc., Chem. Commun., 1990, 1010 RSC ; C. J. Hawker and J. M. J. Fréchet, J. Am. Chem. Soc., 1990, 112, 7638 CrossRef CAS .
  6. T. Tsunoda, Y. Yamamiya, Y. Kawamura and S. Ito, Tetrahedron Lett., 1995, 36, 2529 CrossRef CAS ; O. Mitsunobu, Synthesis, 1981, 1 CrossRef CAS .
  7. A. S. Hay, J. Org. Chem., 1962, 27, 3320 CrossRef CAS .
  8. H. Tanaka, M. Thakur, M. A. Gomez and A. E. Tonelli, Polymer, 1991, 32, 1834 CrossRef CAS .
  9. K. P. C. Vollhardt, Organic Chemistry, Freeman, New York, 1987, p. 519 Search PubMed .
  10. For a discussion of the bonding in buta-1,3-diyne, see: D. A. Plattner, Y. Li and K. N. Houk, in Modern Acetylene Chemistry, ed. P. J. Stang and F. Diederich, VCH, Weinheim, 1995, p. 1 Search PubMed .
  11. C. B. Gorman, Adv. Mater., 1997, 9, 1117 CrossRef CAS ; P. J. Dandliker, F. Diederich, A. Zingg, J.-P. Gisselbrecht, M. Gross, A. Louati and E. Sanford, Helv. Chim. Acta, 1997, 80, 1773 CrossRef CAS .
  12. M. Schreiber, Doctoral Dissertation, ETH Zürich, No. 11904, 1996 .
Click here to see how this site uses Cookies. View our privacy policy here.