A sulfur-containing hetero-octulene: synthesis, host-guest properties, and transistor applications.

A heterocycloarene derivative (S-Octulene) possessing two sulfur atoms was conveniently synthesized through Bi(OTf)3-catalyzed cyclization from a macrocyclic tetramethoxyethenylated precursor. The physical properties of S-Octulene and its supramolecular host-guest interaction with C60 and C70 were investigated by fluorescence titration and 1H NMR. The solution-processed organic field-effect transistor (OFET) measurements demonstrated that S-Octulene behaved as a p-type semiconductor with a hole mobility exceeding 0.01 cm2 V-1 s-1. Our findings pave a new path to design novel heterocycloarenes for the development of host-guest chemistry and organic semiconductors.