Fluorescent Halogen Bonding Arylethynyl Scaffolds For Anion Recognition


­The synthesis of new molecules designed to bind or sense and report the presence of a particular substrate is an area of chemistry that is attracting attention. There exists a general lack of ligand-specific host molecules, such as specific hosts for toxic ions and small molecules of interest. There also is a dearth of specific hosts that report binding events, for example by exhibiting a spectral shift upon binding, such as an altered fluorescent response. In fact, structures of fluorescent coordination complexes are generally poorly understood, which makes the rational design of functional hosts and sensors a challenging undertaking.

Interest in supramolecular sensors for the detection of analytes has received considerable attention over the past two decades. Such systems exploit non-covalent interactions between a guest molecule and a host molecule to induce a change in the host (e.g. NMR shift, color, fluorescence, electrochemical behavior etc.). These systems are advantageous when compared to chemodosimeters because these non-covalent interactions are reversible, which allows one to monitor an analyte dynamically. Arguably the most powerful of these sensors exploit a fluorescence/colorimetric change due to their inherent sensitivity.

The detection of ionic species, in particular the selective detection of a particular ionic species in the presence of another is difficult. The detection of anionic species is a particular challenge, as anions are difficult to bind and are generally larger than cations leading to a smaller charge-to-radius ratio.

In addition, preorganization is a central tenet of supramolecular chemistry that facilitates precise molecular function and higher order self-assembly. Preorganized biomolecular structures rely on noncovalent interactions for their critical role in natural processes (e.g. catalysis, ion channels, signaling, nutrient transport, and antibodies).

US Patent #11,021,447

Patent Information:
For Information, Contact:
Jim Deane
University of Oregon
Darren Johnson
Michael Haley
Jessica Lohrman