Exploring intramolecular π-π interactions in conjugated polymers

ORGN 99

Anne J. McNeil, amcneil@mit.edu, Peter Mueller, and Timothy M. Swager. Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Ave, Cambridge, MA 02139
We are exploring co-facial π-π interactions to modulate the electronic and photophysical properties of π-conjugated materials. We have synthesized a series of rigid molecular scaffolds with co-facial π-π interactions and incorporated them into poly(p-phenylene butadiynylene)s (e.g., 1 and 2). The monomers are prepared using highly selective and high yielding Diels–Alder cycloadditions between anthracene and substituted anhydrides. Monomer x-ray crystal structures show close arene-arene distances (3.0-3.8 Å). High molecular weight poly(p-phenylene butadiynylene)s were prepared via Pd/Cu(I)/benzoquinone oxidative coupling of the diacetylene monomers. The electronic and photophysical properties of these unique conjugated polymers will also be discussed.