Two-level self-assembly from nanowires to microrods based on a heterotriangulene derivative

Compound 1 was synthesized by a palladium-catalyzed Sonogashira cross-coupling reaction of heterotriangulene derivative 3 with three equiv. of 1-dodecyloxy-4-ethynylbenzene 2 in good yield. After the dichloromethane solution of 1 was mixed with methanol, two-level self-assembly from nanowires to microrods based on 1 was obtained and characterized with scanning electron microscopy (SEM), transmission electron microscopy (TEM) and X-ray diffraction (XRD). The driving force of the two-level self-assembly is attributed to the strong π–π stacking interactions of heterotriangulene cores and the hydrophobic interactions of alkyl chains with solvent molecules.