Oligophenylene rods: A repetitive approach

Liebigs Annales

Volumn , Issue 7, 1996, Pages 1037-1040

  Liess, Petra ^a   Hensel, Volker ^a   Schlüter, A Dieter ^a  

^a FREIE UNIVERSITÄT BERLIN   (Germany)

Author keywords

Exponential growth; Molecular rods; Oligophenylenes; Repetitive synthesis; Telechelics

Indexed keywords

EID: 33749126520     PISSN: 09473440     EISSN: None     Source Type: Journal    
DOI: 10.1002/jlac.199619960703     Document Type: Article

References (19)

1. E. Igner, O. I. Paynter, D. J. Simmonds, M. C. Whiting, J. Chem. Soc., Perkin Trans. 1 1987, 2447.
2. J. S. Moore, J. Zhang, Angew. Chem. Int. Ed. Engl. 1992, 31, 922;
3. Angew. Chem. 1992, 104, 873.
4. J. S. Schumm, D. L. Pearson, J. M. Tour, Angew. Chem. Int. Ed. Engl. 1994, 33, 1360;
5. Angew. Chem. 1994, 106, 1445.
6. A.-D. Schlüter, G. Wegner, Acta Polym. 1993, 59, 44.
7. For other oligophenylene syntheses, see: H. A. Staab, F. Binnig, Chem. Ber. 1967, 100, 293;
8. Y. Fujioka, Bull. Chem. Soc. Jpn. 1984, 57, 3494;
9. D. J. Cram, T. Kaneda, R. C. Helgeson, S. B. Brown, C. B. Knobler, E. Maverick, K. N. Trueblood, J. Am. Chem. Soc. 1985, 107, 3645-3657.
10. P. Kaszynski, A. C. Riedli, J. Michl, J. Am. Chem. Soc. 1992, 114, 601.
11. [6] in which modules are used (like the sticks and connectors in a set of children's tinkertoys) to construct objects, the building blocks correspond to the module tick and the coupling chemistry to the module connector. The coupling results in an object that may be used to construct larger objects (e.g., a long rod) in which case it acts as a module.
12. See, for example: B. C. Harris, G. H. Hovakeenian, Y.-H. Lai, H. Mestdagh, K. P. C. Vollhardt, J. Am. Chem. Soc. 1985, 107, 5670.
13. W. P. Weber, Silicon Reagents for Organic Synthesis, Springer, Berlin, 1983.
14. See, for example: M. Rehahn, A.-D. Schlüter, G. Wegner, W. J. Feast, Polymer, 1989, 30, 1060.
15. N. Miyaura, T. Yanagi, A. Suzuki, Synth. Commun. 1981, 11, 513;
16. N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457.
17. G. W. Gray, M. Hird, D. Lacey, K. J. Toyne, J. Chem. Soc., Perkin Trans. 2 1989, 2041.
18. Compound 1(2) was prepared from 2,5-dihexyl-4-bromoiodobenzene and 4-TMS-benzene boronic acid by using the Suzuki reaction on the 30-g scale.
19. For the synthesis of oligophenylene rods with up to 15 benzene rings by using an excess approach, see: P. Galda, M. Rehahn, Synthesis 1996, in press.