Synthesis and analysis of a new class of hydrogen bonding receptors incorporating phenyl acetylene scaffolds

ORGN 361

Calden Stimpson, cstimpso@uoregon.edu, Orion B. Berryman, oberryma@uoregon.edu, Charles A. Johnson II, cajohnso@uoregon.edu, Darren W. Johnson, dwj@uoregon.edu, and Michael M. Haley, haley@uoregon.edu. Department of Chemistry and Materials Science Institute, University of Oregon, University of Oregon, Eugene, OR 97403
Functionalized phenylacetylene scaffolds have shown broad applicability as rigid, linear subunits in the synthesis of shape-persistent supramolecular coordination complexes. Their planarity and conjugation pathways allow host-guest complexation in these systems to be observed due to the change in electronics (e.g. absorption) upon a binding event, such as in the pyridine system below. Easily substituted arene subunits should lend tunability to the host system via bite angle, cavity size, or hydrogen bonding. Herein we report the synthesis and binding studies of a class of sulfonamide and urea receptor complexes with a series of anions and oxoanions.