Download PDF
Synthesis 2001(14): 2143-2155
DOI: 10.1055/s-2001-18066
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Pyrene Containing Building Blocks for Dendrimer Synthesis

Claudia Modrakowski, Silvia Camacho Flores, Matthias Beinhoff, A. Dieter Schlüter*
Freie Universität Berlin, Institut für Chemie, Takustr. 3, 14195 Berlin, Germany
Fax: +49(30)838 53357; e-Mail: adschlue@chemie.fu-berlin.de;
Further Information

Publication History

Received 26 June 2001
Publication Date:
09 August 2004 (online)

    Permissions and Reprints All articles of this category

Abstract

Efficient syntheses of the novel, pyrene containing branched building blocks 10, 13, 22, 25 and of a pyrene based core molecule 16 for the construction of dendrimers are reported. The main tool is a Suzuki cross-coupling. The functional groups for further growth are amines and carboxylic acids, which were used in an orthogonally protected fashion. It was proven that the building blocks could be assembled to a low generation dendrimer 17.

Key words

arenas - dendrimers - cross-coupling - pyrenes - protecting groups

    References

  • For general information about dendrimers see for example:
  • 1a Newkome GR. Moorefield CN. Vögtle F. Dendritic Molecules - Concepts, Syntheses, Perspectives   VCH; Weinheim: 1996. 
    CrossrefGoogle Scholar
  • 1b Zeng F. Zimmerman SC. Chem Rev.  1997,  97:  1681 
    CrossrefGoogle Scholar
  • 1c Bosman AW. Janssen HM. Meijer EW. Chem Rev.  1999,  99:  1665 
    CrossrefGoogle Scholar
  • 1d Fischer M. Vögtle F. Angew. Chem. Int. Ed.  1999,  38:  885 
    CrossrefGoogle Scholar
  • 1e Schlü-ter AD. Rabe JP. Angew. Chem. Int. Ed.  2000,  39:  864 
    CrossrefGoogle Scholar
  • 2 For an elegant study on electron transfer in a dendrimer from a porphyrine core through a Fréchet-type shell, see: Jiang D.-L. Aida T. J. Am. Chem. Soc.  1998,  120:  10895 
    CrossrefGoogle Scholar
  • For the related antenna effect in dendrimers and a comprehensive survey of methods with which the interior of dendrimers have been investigated, see:
  • 3a Hecht S. Fréchet JMJ. Angew. Chem. Int. Ed.  2001,  40:  74 ; and references therein
    Google Scholar
  • 3b Gust D. Moore TA. Adv. Photochem.  1992,  16:  1 
    Google Scholar
  • 3c Burrell AK. Wasieleski MR. J. Porphyr. Phthalocya.  2000,  4:  401 
    Google Scholar
  • 4 Beinhoff M. Modrakowski C. Weigel W. Rettig W. Schlüter AD. Mater. Sci. Engin.  2001,  84:  751 
    Google Scholar
  • For example, see:
  • 6a Voit B. Wolf D. Tetrahedron  1997,  53:  15535 
    CrossrefGoogle Scholar
  • 6b Mulders SJE. Brouwer AJ. van der Meer PGJ. Liskamp RMJ. Tetrahedron Lett.  1997,  38:  631 
    CrossrefGoogle Scholar
  • 6c Mulders SJE. Brouwer AJ. Liskamp RMJ. Tetrahedron Lett.  1997,  38:  3085 
    CrossrefGoogle Scholar
  • 6d Neubert I. Schlüter AD. Macromolecules  1998,  31:  9372 
    CrossrefGoogle Scholar
  • 6e Yamakawa Y. Ueda M. Takeuchi K. Asai M. Macromolecules  1999,  32:  8363 
    CrossrefGoogle Scholar
  • 6f Appelhans D. Komber H. Voigt D. Häussler L. Voit B. Macromolecules  2000,  33:  9494 
    CrossrefGoogle Scholar
  • 6g Shu L. Schäfer A. Schlüter AD. Macromolecules  2000,  33:  4321 
    CrossrefGoogle Scholar
  • 6h Shu L. Schlüter AD. Macromol. Chem. Phys.  2000,  201:  239 
    CrossrefGoogle Scholar
  • 6i Brouwer AJ. Mulders SJE. Liskamp RMJ. Eur. J. Org. Chem.  2001,  1903 
    CrossrefGoogle Scholar
  • 6j Vetter S. Koch S. Schlüter AD. J. Polym. Sci., Polym. Chem.  2001,  39:  1940 
    CrossrefGoogle Scholar
  • 8 Hensel V. Schlüter AD. Chem. - Eur. J.  1999,  5:  421 ; and references cited therein
    Google Scholar
  • 9 Suzuki A. J. Organomet. Chem.  1999,  576:  147 
    Google Scholar
  • 10 Achira JN. Astik RR. Thaller KA. J. Inst. Chem.  1975,  47:  247 
    Google Scholar
  • 11 Ueda Y, Hattori H, Yamamoto J, and Hashimoto K. inventors; Brit. UK Pat Appl., CODEN: Baxxon GB 2207 683, A1  19890208. 
  • 12 Schlüter AD. J. Polym. Sci., Polym. Chem.  2001,  39:  1533 
    CrossrefGoogle Scholar
  • 13 Miyaura N. Ishiyamo T. Ishikawa M. Suzuki A. Tetrahedron Lett.  1986,  27:  6369 
    Google Scholar
  • 15a Houben-Weyl, Methoden der Organischen Chemie   4th ed., Vol. XV:  Wünsch E. Thieme; Stuttgart: 1974.  p.103ff 
    Google Scholar
  • 15b Houben-Weyl, Methoden der Organischen Chemie   4th ed., Vol. II:  Wünsch E. Thieme; Stuttgart: 1974.  p.326ff 
    Google Scholar
  • 16 Hensel V. Schlüter AD. Lieb. Ann./Recueil  1997,  303 
    Google Scholar
  • 17a Stille JK. Angew. Chem.  1986,  98:  504 
    Google Scholar
  • 17b Ogino K. Iwashima S. Inokuchi H. Harada Y. Bull. Chem. Soc. Jpn.  1965,  38:  474 
    Google Scholar
  • 18 For example, see: Langhals H. Demmig S. Potrawa T. J. Prakt. Chem.  1991,  333:  733 
    CrossrefGoogle Scholar
  • 19 For a synthesis which was not used here, see: Blight MM. Coppen JJW. Grove JF. J. Chem. Soc. (C)  1969,  552 
    Google Scholar
  • 20 Beer MS. J. Med. Chem.  1993,  36:  1529 
    CrossrefPubMedGoogle Scholar
  • 21 Vollmann H. Becker H. Corell M. Streeck H. Langbein G. Lieb. Ann. Chem.  1937,  531:  1 
    Google Scholar
  • 22 Takuwa A. Kanaue T. Yamashita K. Nishigaishi Y. J. Chem. Soc., Perkin Trans.(1)  1998,  1309 
    CrossrefGoogle Scholar
5

Beinhoff, M.; Weigel, W.; Jurczok, M.; Rettig, W.; Modrakowski, C.; Brüdgam, I.; Hartl, H.; Schlüter, A. D. Eur. J. Org. Chem. submitted.

7

We consider a dummy a non-fluorescent fragment of virtually the same space demand as the fluorescent probe.

14

For example, see: Vetter, S.; Zhang, A.; Koch, S.; Schlüter, A. D. Macromol. Chem. Phys. submitted.