Synthesis of novel low-bandgap organic semiconductors: Azulene-1,3-diyl-vinylene oligomers
A. Strachotaa,b*, V. Cimrováa, E. Thorn-Csányib
a Institute of Macromolecular Chemistry, Academy of Sciences of the Czech Republic, Heyrovského nám. 2, CZ-162 06 Praha 6, Czech Republic
b Institute for Technical and Macromolecular Chemistry, University of Hamburg, Bundesstrasse 45, D-20146 Hamburg, Germany
The synthesis and characterization of azulene-1,3-diyl-vinylene oligomers is described. The oligomers were synthesized by olefin metathesis polymerization of 1,3-diprop-1-enylazulene. Monodisperse azulenediyl-vinylene oligomers were isolated by column chromatography. The products were characterized by 1H-NMR and UV/Vis spectroscopy.
The development of an optimal 1,3-diprop-1-enylazulene (monomer) synthesis is also discussed, as well as an alternative azulenediyl-vinylene oligomer synthesis using the McMurry reaction.
Fig.: Synthesis of azulene-1,3-diyl-vinylene oligomers
The authors thank the University of Hamburg and the Ministry of Education, Youth and Sports of the Czech Republic (grant No.1M06031) for the financial support of this work.