I spent two years conducting undergraduate research and learning the art of organic synthesis in the gorgeous Molecular Foundry at Lawrence Berkeley National Laboratory in Dr. Yi Liu’s Group. The highlights of my first research experience are described below.
Multistate Molecular Switches. My first undergraduate research project entailed the synthesis of catenanes containing four different aromatic stations that are all electrochemically active. Some of the catenanes exhibited reversible electrochemical switching between six different states (J. Am. Chem. Soc. 2010, 132, 1110).
Dynamic Covalent Chemistry. I worked with another undergraduate student, Gayane Koshkarayan, to demonstrate that a linear dumbbell-shaped bipyridinium molecule can template cage formation around itself through sixfold imine bond formation to give an interlocked rotaxane as the single product (Angew. Chem. Int. Ed. 2009, 48, 4185). This highly efficient [2+3] clipping occurs despite the symmetry mismatch between the template and the formed macrobicycle. An analogous [2+2] clipping reaction can be employed to synthesize dynamic catenanes (Org. Lett. 2010, 12, 1528).
Discotic Molecules. My final project involved the synthesis and purification of tris(aroyleneimidazole) derivatives. I was able to isolate pure compound during my last week in Berkeley. These molecules exhibit desirable bandgaps, broad absorptions, high thermal stabilities, and tend to self-assemble into fibers (Chem. Commun. 2011, 47, 3454).