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Connecting Curable Siloxanes to Luminescent Organic Semiconductors - Monomers for Functional Hybrid Materials

Published online by Cambridge University Press:  01 February 2011

Heiner Detert
Affiliation:
detert@mail.uni-mainz.de, Johannes Gutenberg-Universität Mainz, Institut für Organische Chemie, Duesbergweg 10 - 14, Mainz, Rheinland-Pfalz, 55099, Germany, ++49-6131-3922111
Erli Sugiono
Affiliation:
e.sugiono@chemie.uni-frankfurt.de, Johann Wolfgang Goethe-Universität Frankfurt, Frankfurt/Main, N/A, 60444, Germany
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Abstract

Luminescent stilbenoid chromophores with two alkoxysilane end groups are prepared via hydrosilylation or condensation / reduction of substituted 5-ring OPVs with hydro- and aminopropylsilanes. Chromophore and curable units are connected via flexible spacers. To obtain compounds with a rigid connection between silane and π-system, iodo- or bromo-OPVs were coupled to alkoxysilanes carrying vinyl- or p-vinylphenyl moieties under Heck conditions. This approach allowed a combined connection of the chromophore to the silane moiety with an extension of the π-system. Hydrolysis of the alkoxysilanes yields silanols condensing to curable three-dimensional networks, thus allowing the transformation of small molecules to transparent and fluorescent films with well-defined chromophores.

Type
Research Article
Copyright
Copyright © Materials Research Society 2006

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