164991-12-2Relevant articles and documents
A Novel "Double-Coupling" Strategy for Iterative Oligothiophene Synthesis Using Orthogonal Si/Ge Protection
Spivey, Alan C.,Turner, David J.,Turner, Michael L.,Yeates, Stephen
, p. 1899 - 1902 (2002)
(Matrix Presented) A new iterative synthesis of regioregular oligothiophenes has been developed in which "double-coupling" after each iteration minimizes deletion sequences. The method exploits the susceptibility of α-silyl- but not α-germyl-substituted thiophene derivatives toward nucleophilic ipso-protodemetalation and features an unusual "base-free" Suzuki-type cross-coupling protocol. The strategy has been designed for the solid-phase synthesis of high purity oligothiophenes using a germanium-based linker.
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.