PDF herunterladen
Synthesis 2009(1): 79-84  
DOI: 10.1055/s-0028-1083260
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Functionalized Oligophenylenes and Oligoarylenes Bearing Heteroaryl Groups

Ivonne Wallmanna, Gregor Schnakenburgb, Arne Lützen*a
a Kekulé-Institute of Organic Chemistry and Biochemistry, University of Bonn, Gerhard-Domagk-Str. 1, 53121 Bonn, Germany
Fax: +49(228)739608; e-Mail: arne.luetzen@uni-bonn.de;
b Institute of Inorganic Chemistry, University of Bonn, Gerhard-Domagk-Str. 1, 53121 Bonn, Germany
Weitere Informationen

Publikationsverlauf

Received 20 October 2008
Publikationsdatum:
12. Dezember 2008 (online)

    Lizenzen und Reprints Alle Artikel dieser Rubrik

Abstract

Oligo-p-phenylenes have proven to be versatile building blocks for the generation of self-assembled nanoaggregates via vapour deposition on solid supports whose optical properties and morphologies can be influenced by the introduction of functional groups. These aggregates show strong polarized luminescence and they have been demonstrated to have wave-guiding, lasing and even non-linear optical properties (e.g., frequency doubling) when the molecular building blocks are suitably functionalized. Thus, there is a demand for the synthesis of further functionalised p-phenylenes because similar properties can be expected from derivatives incorporating heteroaryl groups in the oligoarylene scaffold such as thiophenes, pyridines or carbazole units. The synthesis of such derivatives using a reliable Suzuki cross-coupling strategy is presented here.

Key words

π-conjugated molecules - oligo-p-phenylenes - thiophenes - carbazoles - Suzuki cross-coupling

    References

  • 1a Schwab PFH. Levin MD. Michl J. Chem. Rev.  2005,  105:  1197 
    Google Scholar
  • 1b Schwab PFH. Michl J. Smith JR. Chem. Rev.  2005,  105:  1197 
    Google Scholar
  • Some recent books:
  • 2a Müllen K. Wegner G. Electronic Materials: The Oligomer Approach   Wiley-VCH; Weinheim: 1998. 
    Google Scholar
  • 2b Fichou D. Handbook of Oligo- and Polythiophenes   Wiley-VCH; Weinheim: 1999. 
    Google Scholar
  • 2c Nalva HS. Handbook of Advanced Electronic and Photonic Materials and Devices   Academic Press; San Diego: 2000. 
    Google Scholar
  • 2d Müllen K. Scherf U. Organic Light Emitting Devices - Synthesis, Properties and Applications   Wiley-VCH; Weinheim: 2006. 
    Google Scholar
  • 2e Klauk H. Organic Electronics - An Industrial Perspective   Wiley-VCH; Weinheim: 2006. 
    Google Scholar
  • 2f Müller TJJ. Bunz UHF. Functional Organic Materials   Wiley-VCH; Weinheim: 2007. 
    Google Scholar
  • 3 Organic Nanostructures for Next Generation Devices   Al-Shamery K. Rubahn H.-G. Sitter H. Springer; Berlin: 2008. 
    Google Scholar
  • 4a Schiek M. Balzer F. Al-Shamery K. Brewer J. Lützen A. Rubahn H.-G. Small  2008,  4:  176 
    Google Scholar
  • 4b Schiek M. Balzer F. Al-Shamery K. Lützen A. Rubahn H.-G. Soft Matter  2008,  4:  277 
    Google Scholar
  • 5a Schiek M. Al-Shamery K. Lützen A. Synthesis  2007,  613 
    Google Scholar
  • 5b Wallmann I. Schiek M. Koch R. Lützen A. Synthesis  2008,  2446 
    Google Scholar
  • 6 Khlobystov AN. Brett MT. Blake AJ. Champness NR. Gill PMW. O’Neill DP. Teat SJ. Wilson C. Schröder M. J. Am. Chem. Soc.  2003,  125:  6753 
    CrossrefGoogle Scholar
  • 7 Frohn HJ. Klose A. J. Fluorine Chem.  1993,  64:  201 
    CrossrefGoogle Scholar
  • 8 Korenga T. Kosaki T. Fukumura R. Ema T. Sakai T. Org. Lett.  2005,  7:  4915 
    CrossrefGoogle Scholar
  • 9a Freeman AW. Urvoy M. Criswell ME. J. Org. Chem.  2005,  70:  5014 
    Google Scholar
  • 9b Moon K.-S. Kim H.-J. Lee M. Angew. Chem. Int. Ed.  2007,  46:  6807 
    Google Scholar
  • 10 Simpson E. Daup H. Hayes FN. J. Org. Chem.  1973,  38:  4428 
    CrossrefGoogle Scholar
  • 11 Otwinowski Z. Minor W. Methods Enzymol.  1997,  276:  307 
    Google Scholar
  • 12 Otwinowski Z. Borek D. Majewski W. Minor W. Acta Crystallogr., Sect. A  2003,  59:  228 
    CrossrefPubMedGoogle Scholar
  • 13a Sheldrick GM. Acta Crystallogr., Sect. A  1990,  46:  467 
    Google Scholar
  • 13b Sheldrick GM. SHELXL-97 Program for Crystal Structure Analysis   University of Göttingen; Germany: 1997. 
    Google Scholar