Dendritic and hyperbranched polyphenylenes via a simple Diels-Alder route

Tetrahedron

Volumn 53, Issue 45, 1997, Pages 15349-15366

  Morgenroth, Frank ^a   Müllen, Klaus ^a  

^a MAX PLANCK INSTITUTE FOR POLYMER RESEARCH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE DERIVATIVE; BIPHENYL; ORGANIC COMPOUND; TETRAPHENYLCYCLOPENTADIENONE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; PRIORITY JOURNAL; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

BETULACEAE;

EID: 17044456499     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00967-8     Document Type: Article

References (43)

1. Diels, O.; Alder, K., Liebigs Ann. Chem. 1928, 460, 98-122.
2. Sauer, J.; Sustmann, R., Angew. Chem. Int. Ed. Engl. 1980, 19, 779.
3. Wetzel, P., Nachr. Chem. Techn. Lab. 1983, 31, 979-983.
4. Woodward, R. B.; Sondheimer, F.; Taub, D.; Heusler, K.; McLamore, W. M., J. Am. Chem. Soc. 1951, 73, 2403-2404.
5. Stork, G.; van Tamelen, E. F.; Friedman, L. J.; Burgstahler, A. W., J. Am. Chem. Soc. 1951, 73, 4501.
6. Stille, J. K., Die Makromolekulare Chemie 1972, 154, 49-61.
7. Kumar, U.; Neenan, T. X., Macromolecules 1995, 28, 124-130.
8. Horn, T.; Wegener, S.; Müllen, K., Macromol. Chem. Phys. 1995, 196, 2463-2474; Müller, A.; Stadler, R., Macromol. Chem. Phys. 1996, 197, 1373-1385.
9. Horn, T.; Wegener, S.; Müllen, K., Macromol. Chem. Phys. 1995, 196, 2463-2474; Müller, A.; Stadler, R., Macromol. Chem. Phys. 1996, 197, 1373-1385.
10. Schlüter, A. D., Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 1995, 36, 592-593; Löffler, M.; Schlicke, B.; Schirmer, H.; Schlüter, A. D., Macromol. Symp. 1994, 87, 5-9.
11. Schlüter, A. D., Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 1995, 36, 592-593; Löffler, M.; Schlicke, B.; Schirmer, H.; Schlüter, A. D., Macromol. Symp. 1994, 87, 5-9.
12. Kirchhoff, R. A.; Bruza, K. J., Adv. Polym. Sci 1994, 117, 66-69; Kirchhoff, R. A.; Hahn, S. F., Dow Chemical, US Pat. 1989, 4687823 A; Kirchhoff, R. A.; Schrock, A. K.; Hahn, S. F., Dow Chemical, US Pat. 1989, 8705303 A1.
13. Kirchhoff, R. A.; Bruza, K. J., Adv. Polym. Sci 1994, 117, 66-69; Kirchhoff, R. A.; Hahn, S. F., Dow Chemical, US Pat. 1989, 4687823 A; Kirchhoff, R. A.; Schrock, A. K.; Hahn, S. F., Dow Chemical, US Pat. 1989, 8705303 A1.
14. Kirchhoff, R. A.; Bruza, K. J., Adv. Polym. Sci 1994, 117, 66-69; Kirchhoff, R. A.; Hahn, S. F., Dow Chemical, US Pat. 1989, 4687823 A; Kirchhoff, R. A.; Schrock, A. K.; Hahn, S. F., Dow Chemical, US Pat. 1989, 8705303 A1.
15. nd Suppl., (eds.: Allen, G.; Aggarwal, S. L.; Russo, S.), Elsevier, Oxford, 1996, pp.70-129.
16. a) Tour, J. M., Adv. Mater. 1994, 6, 190-198;
17. b) Frey, H.; Lorenz, K.; Lach, C., Chemie in unserer Zeit 1996, 2, 75-85;
18. c) Kim, Y. H., US Pat., 1989, 4857630;
19. d) Kim, Y. H.; Webster, O. W., J. Am. Chem. Soc. 1990, 112, 4592-4593;
20. e) Liess, P.; Hensel, V.; Schlüter, A. D., Liebigs Ann. 1996, 1037-1040.
21. Morgenroth, F.; Reuther, E.; Müllen, K., Angew. Chem. Int. Ed. Engl. 1997, 36, 631-634.
22. Morgenroth, F.; Kübel, C.; Müllen, K., J. Mater. Chem., Special Issue on Molecular Assemblies and Nanochemistry 1997, in press.
23. In this context we use the term "dendritic polymer" to describe a regularly branched monodisperse polymer, in which many identical building blocks emanate from a central core to adopt a globular structure when a certain size is reached. For other definitions, see reference [11].
24. Altenbach, H. J. in Organic Synthesis Highlights, (eds.: Mulzer, J.; Altenbach, H. J.; Braun, M.; Krohn, K.; Reissig, H.-U.), VCH, Weinheim, 1991, pp. 181-185.
25. Miller, T. M.; Neenan, T. X.; Zayas, R.; Bair, H. E., J. Am. Chem. Soc. 1992, 114, 1018-1025.
26. Kovacic, P.; Koch, F. W., J. Org. Chem. 1965, 30, 3176-3181.
27. Müller, M.; Mauermann-Düll, H.; Wagner, M.; Enkelmann, V.; Müllen, K., Angew. Chem. Int. Ed. Engl. 1995, 34, 1583-1586;
28. b) Müller, M.; Petersen, J.; Strohmeier, R.; Günther, C.; Karl, N.; Müllen, K., ibid. 1996, 35, 886-888;
29. c) Stabel, A.; Herwig, P.; Müllen, K.; Rabe, J. P., ibid. 1995, 34, 1609-1611;
30. d) Müller, M.; Kübel, C.; Iyer, V. S.; Müllen, K., Angew. Chem. 1997, in press;
31. e) Iyer, V. S.; Wehmeier, M.; Brand, J. D.; Keegstra, M. A.; Müllen, K., Angew. Chem. 1997, in press;
32. f) Müller, M.; Morgenroth, F.; Scherf, U.; Soczka-Guth, T.; Klärner, G.; Müllen, K., Phil. Trans. R. Soc. Lond. 1997, 355 A, 715-725.
33. Dilthey, W.; Schommer, W.; Dierichs, H.; Trösken, O., Ber. 1933, 66, 1627-1628; Dilthey, W.; Hurtig, G., Ber. 1934, 67, 2004-2007.
34. Dilthey, W.; Schommer, W.; Dierichs, H.; Trösken, O., Ber. 1933, 66, 1627-1628; Dilthey, W.; Hurtig, G., Ber. 1934, 67, 2004-2007.
35. Spickermann, J.; Martin, K.; Räder, H. J.; Müllen, K.; Krüger, R. P.; Schlaad, H.; Müller, A. H. E., Eur. Mass Spectrom. 1996, 2, 161; Martin, K.; Spickermann, J.; Räder, H. J.; Müllen, K., Rapid Commun. Mass Spectrom.1996, 10, 1471.
36. Spickermann, J.; Martin, K.; Räder, H. J.; Müllen, K.; Krüger, R. P.; Schlaad, H.; Müller, A. H. E., Eur. Mass Spectrom. 1996, 2, 161; Martin, K.; Spickermann, J.; Räder, H. J.; Müllen, K., Rapid Commun. Mass Spectrom.1996, 10, 1471.
37. In those cases, rearrangement of phenyl rings is observed. For cyclodehydrogenation studies of such "overcrowded" oligophenyls, see reference [19d] .
38. 13C-NMR-Spektroskopie, Georg Thieme, Stuttgart 1984; p. 74.
39. Takahashi, S.; Kuroyama, Y.; Sonogashira, K.; Hagihara, N., Synthesis 1980, 627-630.
40. a) Ogliaruso, M. A.; Romanelli, M. G.; Becker, E. I., Chem. Rev. 1965, 65, 261-367;
41. b) Broser, W.; Reusch, J.; Kurreck, H.; Siegle, P., Chem. Ber. 1969, 702, 1715-1724.
42. For an alternative synthesis of 1e, see : Shifrina Z.; Rusanov, A. L., to be published.
43. van Roosmalen, F. L. W., Recl. Trav. Chim. Pays-Bas 1934, 53, 359-379.