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Issue 39, 2010
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Rapid assembly of explicit, functional silicones

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Abstract

The impressive surface activity of silicones can be enhanced by the incorporation of hydrophilic organic functional groups and polymers. Traditional routes to such compounds, which typically involve platinum-catalyzed hydrosilylation, suffer from incompatibility with certain functional groups. B(C6F5)3-catalyzed condensation of hydrosilanes with alkoxysilanes offers new opportunities to prepare explicit silicone structures. We demonstrate here that conversion of alcohols to silyl ethers competes unproductively with alkoxysilane conversion to disiloxanes. By contrast, a wide range of structurally complex alkyl halide and oligovinyl compounds can be readily made in high yield. Thermal 3+2-cycloadditions and thiol-ene click reactions are used to convert these compounds into surface active materials.

Graphical abstract: Rapid assembly of explicit, functional silicones

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Article information


Submitted
30 Apr 2010
Accepted
17 Jun 2010
First published
16 Aug 2010

Dalton Trans., 2010,39, 9369-9378
Article type
Paper

Rapid assembly of explicit, functional silicones

J. B. Grande, F. Gonzaga and M. A. Brook, Dalton Trans., 2010, 39, 9369
DOI: 10.1039/C0DT00400F

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