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Synthesis 1993; 1993(6): 634-642
DOI: 10.1055/s-1993-25916
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Synthesis of Precursor Molecules for Low Band Gap Polymers

Michael Hanack* , Ulrich Schmid, Stefan Echinger, Frank Teichert, Jürgen Hieber
  • *Institut für Organische Chemie der Universität Tübingen, Auf der Morgenstelle 18, D-7400 Tübingen, Germany
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Publication Date:
17 September 2002 (online)

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The synthesis and characterization of precursors for polyarene- and hetarenemethylenes (PAM) of structure 3, which are predicted to be low band gap polymers are described. The precursor molecules 4 are synthesized from the corresponding 2-thiophene- and 2-pyrrole- carbaldehydes 6a and 6b by Knoevenagel condensation with 2,5-dibydrothiophene 1-oxide (9) and / or the analogous benzo- and naphtho-annulated sulfoxides 9. The sulfoxide groups in 9 are easily reduced with formation of the sulfides 11. The synthesis of the precursor molecules 20-22 containing two directly linked quinoid structures is also described. To increase the solubility of the 1,3-bis(2-thienylmethylene)-1,3-dihydroisothianaphthene systems 4 e.g. alkoxy substituents are introduced into the annulated benzene ring of 4.