Molecular Design

DATB (1,3-Dioxa-5-Aza-2,4,6-TriBorinane), a peculiar six-membered heterocyclic entity without any carbon atoms designed by our group, strongly catalyzes amide bond-forming reactions from carboxylic acids and amines. In contrast to reagent-driven amidation reactions that produce reagent-derived waste, water is the sole by-product in the environmentally sustainable DATB catalysis, which will find its utility in the large-scale production of amide-containing therapeutics. DATB is a thermally stable solid and is now commercially available on a world-wide basis. We aim to further explore DATB catalysis and design/development of novel heterocyclic entities for as-yet unknown molecular functions.

TriQuinoline (TQ) is a head-to-tail quinoline trimer with a pseudo-planar architecture, bearing a one-atomic size defect at the very center of the molecule. TQ strongly holds a proton at the defect to be a charged species, acquiring water-solubility despite its expected lipophilicity. TQ forms supramolecular complexes with other aromatic compounds via both π-π（face to face）and CH-π（edge to face）interactions, allowing for inhibitory effects on cancer cell proliferation and modulation of lipid-lipid phase separation in live cells. The flexible derivatization capability of TQ will be leveraged to identify a new class of functional and bioactive azole-type molecules. Current works are focused on the design and synthesis of a larger three-dimensional architecture to expand the potential of these azole-based molecular entities.

We have identified a new class of fluorescent molecules named C4N4 with a diaminopyrimidine core composed of four carbon and nitrogen atoms. C4N4 fluorescent molecules can be synthesized from commercially available chemicals in a modular fashion, producing strongly luminescent molecules with a large Stokes shift and a solid state emission capability applicable to live-cell bioimaging. We are currently pursuing strategic structural modifications to develop a more sophisticated fluorescent host composed of C4N4 units able to sense specific guest molecules for application as novel CPL molecules.