Self-assembly of o-phenylene ethynylene macrocycles

POLY 673

Jing Jiang, jjiang@polysci.umass.edu1, Sang Hyuk Seo, polyman9@snu.ac.kr2, Ji Young Chang, jichang@snu.ac.kr2, and Gregory Tew, tew@mail.pse.umass.edu3. (1) Department of polymer science and Engineering, University of Massachusetts, Amherst, amherst, MA 01003, (2) School of materials science and engineering, Seoul National University, San 56-1 Sinlim-Dong Kwanak-Gu, Seoul, 151-744, South Korea, (3) Department of Polymer Science and Engineering, University of Massachusetts, 120 Governors Drive, Amherst, MA 01003
A novel ethylene oxide substituted triangular ortho-phenylene ethynylene macrocycle was successfully synthesized. The vesicular morphologies of this amphiphilic macrocycle were studied by atomic force microscopy (AFM), transmission electron microscopy (TEM) and dynamic light scattering (DLS). AFM and TEM showed the macrocycle can self-assemble from aqueous chloroform into vesicles with a bilayer wall thickness of about 3 nm and average diameter of around 500 nm, which was in excellent agreement with the DLS results. The assembled vesicles are robust enough to be dried onto a carbon surface and examined by AFM without collapse. The vesicles collapsed following exposure to the high vacuum of TEM, as confirmed by AFM, but otherwise the morphology remains unchanged. This is the first example of a vesicle formed from an amphiphilic discotic macrocycle.