Perfluorophenyl Polyynes

Significance

Synthesis of perfluorophenyl-containing polyynes presents a challenge due to the electrophilicity of the perfluoro moiety. The authors report straightforward syntheses of both symmetric and asymmetric derivatives ranging from triynes to octaynes. The use of Colvin’s reagent [Me₃SiC(Li)N₂] in the synthesis of 2 is unprecedented in polyyne synthesis. Crystallographic analysis proves the supramolecular packing of all five previously unknown perfluoroaryl polyynes to be consistent with that of shorter derivatives.