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).

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.

Synthesis, solid state structure and polymerisation of a fully planar cyclopentadithiophene.

The new fully planar cyclopentadithiophene, 4-n-dodecylidene-4H-cyclopenta(2,1-b;3,4-b')dithiophene, shows extensive pi-stacking in the solid state with short intermolecular distances (ca. 3.5 A) between adjacent molecules.