691006-33-4Relevant academic research and scientific papers
A Tuneable Ge-based Linker that Enables Application-led Solid Phase Synthesis Optimisation - Towards a Robust Iterative Synthesis of Oligothiophenes
Spivey, Alan C.,Turner, David J.,Turner, Michael L.,Yeates, Stephen
, p. 111 - 115 (2004)
A convenient synthesis of a new dichlorogermanium-based linker-precursor for solid phase synthesis is described that allows facile introduction of a range of 'spectator' substituents (R) onto germanium. Variation of these R groups allows modulation of the stability of the key germanium-carbon bond between the linker and the aryl library. The tuning process is exemplified by application to the optimisation of a linker for the iterative solid-phase synthesis (SPS) of oligothiophenes.
Towards a general solid phase approach for the iterative synthesis of conjugated oligomers using a germanium based linker - First solid phase synthesis of an oligo-(triarylamine)
Turner, David J.,Anemian, Remi,MacKie, Philip R.,Cupertino, Domenico C.,Yeates, Stephen G.,Turner, Michael L.,Spivey, Alan C.
, p. 1752 - 1763 (2008/02/10)
The development of a germanium-based linker system for the solid phase synthesis (SPS) of 3-(n-hexyl)thiophene oligomers and the first SPS of triarylamine oligomers via iterative chain extension is described. The efficiency of the key steps in the oligomer syntheses and their compatibility with the germanium linker are demonstrated by the SPS of bi-[3-(n-hexyl) thiophene] 19 and ter-(triarylamine) 50. The use of a germanium-based linker in combination with appropriately selected silicon-based blocking/protecting groups allows double coupling to drive the key cross coupling steps to completion hence minimising deletion sequences and also allows for traceless and potentially functionalisative cleavage from the resin. The latter feature has yet to be fully explored but towards this end the first ipso-borodegermylation reaction of a 2-germyl-3-(n-hexyl)thiophene is presented. The Royal Society of Chemistry.
