Thymine-functionalised siloxanes: Model compounds and polymers

•Organosiloxanes functionalised with thymine have been prepared using a novel, efficient method.•Condensation of α-amino-ω-alkylsilanes or amino-functionalised siloxanes with thymine aldehydes gave high molecular weight polymers.•Variation in thymine loading led to a range of material properties from highly viscous fluids to brittle solids.

A novel, efficient synthetic method for the production of organosiloxane polymers functionalised with pendant DNA bases, typified by thymine, is reported. A condensation reaction between an α-amino-ω-alkylsilane or an amino-functionalised siloxane with aldehyde-functionalised thymine gave polymers in higher overall yields than the methods previously reported. Variation in the loading of thymine led to a range of material properties from a highly viscous fluid at 0.2% functionalization to a hard, brittle solid at 20% loading due to hydrogen bonding interactions.

Graphical abstractOrganosiloxane polymers functionalised with a pendant DNA base, thymine, have been prepared in high yield by condensation of amino-functionalised siloxanes with aldehyde-functionalised thymine.Figure optionsDownload full-size imageDownload as PowerPoint slide