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Ladder Polymers of High Stability With Macrocyclic Metal Complexes as Subunits

Published online by Cambridge University Press:  10 February 2011

M. Hanack ,
B. Hauschel ,
P. Stihler ,
M. Rack  and
T. Linßen
M. Hanack
Affiliation:
Institut für Organische Chemie, Universität Tübingen, D-72076 Tübingen, Germany
B. Hauschel
Affiliation:
Institut für Organische Chemie, Universität Tübingen, D-72076 Tübingen, Germany
P. Stihler
Affiliation:
Institut für Organische Chemie, Universität Tübingen, D-72076 Tübingen, Germany
M. Rack
Affiliation:
Institut für Organische Chemie, Universität Tübingen, D-72076 Tübingen, Germany
T. Linßen
Affiliation:
Institut für Organische Chemie, Universität Tübingen, D-72076 Tübingen, Germany
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Abstract

Macrocyclic bis-dienes and a diendienophile were prepared in Diels-Alder reactions starting from the bis-dienophilic (hemiporphyrazinato)nickel complex 1. 1 was reacted either with the tetraene 2 or with tetraphenylcyclopentadienone (4). By combination of macrocyclic bisdienes and bis-dienophiles, ladder-type oligomers were synthesized. They are precursors to the corresponding conjugated molecules, which are of interest as potential organic conductors. Monofunctional and bifunctional dienophilic macrocycles were also allowed to react with [60]fullerene to give the corresponding mono- and bis-fullerene adducts.

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References

Literature

1. U. Scherf and K. Müllen, Synthesis 1992, 23, and references therein; Goldfinger, M. B. and Swager, T. B., J. Am. Chem. Soc. 116, 7895 (1994); B. Schlicke, H. Schirmer and A.-D. Schlüter, Adv. Mater. 7, 544 (1995).Google Scholar
2. Tessler, M. M., J. Polym. Sci., Part A–1 1960, 2521.Google Scholar
3. Christophel, W. and Miller, L. C., J. Org. Chem. 51, 4160 (1986); M. Wagner, W. Wohlfarth and K. Mtillen, Chimia 42, 377 (1988); A.-D. Schliiter, Adv. Mater. 3, 282 (1991).Google Scholar
4. Rack, M. and Hanack, M., Angew. Chem. 106, 1712 (1994); Angew. Chem. Int. Ed. Engl. 33, 1646 (1994).Google Scholar
5. Hanack, M. and Lang, M., Adv. Mater. 6, 819 (1994).Google Scholar
6. Gomez-Romero, P., Lee, Y.-S. and Kertesz, M., Inorg. Chem. 27, 3672 (1988).Google Scholar
7. Linßen, T. G. and Hanack, M., Chem. Ber. 127, 2051 (1994).Google Scholar
8. Hanack, M., Schmid, G. and Sommerauer, M., Angew. Chem. 105, 1540 (1993); Angew. Chem. Int. Ed. Engl. 32, 1422 (1993).Google Scholar
9. Elvidge, J. A. and Linstead, R. P., J. Chem. Soc. 1952, 5008; M. Rack, B. Hauschel and M. Hanack, Chem. Ber., in press.Google Scholar
10. Chollet, A., Wismer, M. and Vogel, P., Tetrahedron Lett. 47, 4271 (1976); R. Gabioud and P. Vogel, Tetrahedron 36, 149 (1980).Google Scholar
11. Hauschel, B., Ruff, D. and Hanack, M., J. Chem. Soc., Chem. Commun., in press.Google Scholar
12. Fieser, L. F. and Haddadin, M. J., Can. J. Chem. 43, 1599 (1965); J. Luo and H. Hart, J. Org. Chem. 53, 1341 (1988).Google Scholar
13. Linssen, T. G., Dürr, K., Hanack, M. and Hirsch, A., J. Chem. Soc., Chem. Commun. 1995, 103.Google Scholar
14. Fiedler, S., PhD thesis, Universität Tübingen, 1995.Google Scholar