An oligo(p-phenylenevinylene) (OPV)-substituted hexaarylbenzene has been synthesized and fully characterized. Recycling gel permeation chromatography appeared to be a powerful technique to obtain the OPV molecules in a very pure form. X-ray analysis and polarization optical microscopy revealed that the OPV molecule is plastic crystalline at room temperature with an ordered columnar superstructure. In apolar solvents, the molecules self-assemble via a highly cooperative fashion into right-handed chiral superstructures, which are stable even at high temperatures and low concentration. Atomic force microscopy revealed right-handed fibers with a diameter of 6 nm, indicating π-stacked aggregates; on a silicon oxide substrate, supercoiled chiral structures were observed. STM studies on a liquid−solid interface showed that the star-shaped OPV molecule forms an organized monolayer having a chiral hexagonal lattice.
Tomovic, Z., Van Dongen, J., George, S. J., Xu, H., Pisula, W., Leclère, P. E. L. G., Smulders, M. M. J., Feyter, de, S., Meijer, E. W., & Schenning, A. P. H. J. (2007). Star-shaped oligo(p-phenylenevinylene) substituted hexaarylbenzene: Purity, stability, and chiral self-assembly. Journal of the American Chemical Society, 129(51), 16190-16196. https://doi.org/10.1021/ja0765417