Acetylenic scaffolding on solid support: poly(triacetylene)-derived oligomers by Sonogashira and Cadiot-Chodkiewicz-type cross-coupling reactions.

We report the first synthesis of poly(triacetylene)-derived oligomers by Pd(0)-catalysed Sonogashira and Cadiot-Chodkiewicz-type cross-coupling reactions on solid support. Oligo(phenylene triacetylene)s, members of a new class of linearly pi-conjugated oligomers with all-carbon backbones, feature very high fluorescence intensities.

Novel extended tetrathiafulvalenes based on acetylenic spacers: synthesis and electronic properties.

A selection of mono- and diacetylenic dithiafulvalenes was synthesized and employed for the construction of extended tetrathiafulvalenes (TTFs) with hexa-2,4-diyne-1,6-diylidene or deca-2,4,6,8-tetrayne-1,10-diylidene spacers between the two 1,3-dithiole rings. By stepwise acetylenic scaffolding using (E)-1,2-diethynylethene (DEE) building blocks, an extended TTF containing a total of 18 C(sp) and C(sp(2)) atoms in the spacer was prepared. The versatility of the acetylenic dithiafulvene modules was also established by the efficient synthesis of a thiophene-spaced TTF, employing a palladium-catalyzed cross-coupling reaction.