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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
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Publication History

Received 20 October 2008
Publication Date:
12 December 2008 (online)

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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 
    Search in Google Scholar
  • 1b Schwab PFH. Michl J. Smith JR. Chem. Rev.  2005,  105:  1197 
    Search in Google Scholar
  • Some recent books:
  • 2a Müllen K. Wegner G. Electronic Materials: The Oligomer Approach   Wiley-VCH; Weinheim: 1998. 
  • 2b Fichou D. Handbook of Oligo- and Polythiophenes   Wiley-VCH; Weinheim: 1999. 
  • 2c Nalva HS. Handbook of Advanced Electronic and Photonic Materials and Devices   Academic Press; San Diego: 2000. 
  • 2d Müllen K. Scherf U. Organic Light Emitting Devices - Synthesis, Properties and Applications   Wiley-VCH; Weinheim: 2006. 
  • 2e Klauk H. Organic Electronics - An Industrial Perspective   Wiley-VCH; Weinheim: 2006. 
  • 2f Müller TJJ. Bunz UHF. Functional Organic Materials   Wiley-VCH; Weinheim: 2007. 
  • 3 Organic Nanostructures for Next Generation Devices   Al-Shamery K. Rubahn H.-G. Sitter H. Springer; Berlin: 2008. 
  • 4a Schiek M. Balzer F. Al-Shamery K. Brewer J. Lützen A. Rubahn H.-G. Small  2008,  4:  176 
    Search in Google Scholar
  • 4b Schiek M. Balzer F. Al-Shamery K. Lützen A. Rubahn H.-G. Soft Matter  2008,  4:  277 
    Search in Google Scholar
  • 5a Schiek M. Al-Shamery K. Lützen A. Synthesis  2007,  613 
  • 5b Wallmann I. Schiek M. Koch R. Lützen A. Synthesis  2008,  2446 
  • 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 
    CrossrefSearch in Google Scholar
  • 7 Frohn HJ. Klose A. J. Fluorine Chem.  1993,  64:  201 
    CrossrefSearch in Google Scholar
  • 8 Korenga T. Kosaki T. Fukumura R. Ema T. Sakai T. Org. Lett.  2005,  7:  4915 
    CrossrefSearch in Google Scholar
  • 9a Freeman AW. Urvoy M. Criswell ME. J. Org. Chem.  2005,  70:  5014 
    Search in Google Scholar
  • 9b Moon K.-S. Kim H.-J. Lee M. Angew. Chem. Int. Ed.  2007,  46:  6807 
    Search in Google Scholar
  • 10 Simpson E. Daup H. Hayes FN. J. Org. Chem.  1973,  38:  4428 
    CrossrefSearch in Google Scholar
  • 11 Otwinowski Z. Minor W. Methods Enzymol.  1997,  276:  307 
    Search in Google Scholar
  • 12 Otwinowski Z. Borek D. Majewski W. Minor W. Acta Crystallogr., Sect. A  2003,  59:  228 
    CrossrefPubMedSearch in Google Scholar
  • 13a Sheldrick GM. Acta Crystallogr., Sect. A  1990,  46:  467 
    Search in Google Scholar
  • 13b Sheldrick GM. SHELXL-97 Program for Crystal Structure Analysis   University of Göttingen; Germany: 1997.