Dr. Karelle Aiken
- B. S. Williams College (2000)
- Ph.D. University of New Hampshire (2005)
In my lab, all research assistants are trained to carry out air-sensitive, microscale reactions; use analytical instruments; interpret spectroscopic data and to properly record their findings and observations in laboratory notebooks. They optimize procedures, provided samples for analysis with High Resolution Mass Spectrometry (HRMS), acquire and interpret 1D and 2D NMR spectra for structure determination. In addition, the undergraduate research assistants are taught to use databases such as SciFinder and Web of Science to search for relevant literature, the school’s interlibrary loan system and, they are given many opportunities to refine their scientific communication skills with presentations during group meetings, at on-campus research symposia and, at national and regional conferences. Two projects are currently underway:
I. The Electrophilic Activation of Alkynes for Nucleophilic Attack in the Synthesis of Furanylidene Building Blocks
This project is focused on generating furanylidene building blocks from unique substrates1 via furanylidenes 2. There are number of promising molecules with furanylidene (and furan) cores, for example compounds with antiplasmodial, antibacterial and cytotoxic activity, eg. Nodulisporacid and 5H-furan-2-one from Aporium caryae. There is therefore the potential for our alkynylated furanylidenes 2 to be used in the synthesis of pharmaceutically important compounds and their analogues. We could further derivatize/expand on 2 at at-least three positions, the alkyne, enol-ether and carbonyl moieties.
Figure 1: Examples of biologically active compounds with furanylidene cores
II. Synthesis of Polyaryls via Aryl-Aryl coupling reactions
This project will create new oligomeric, organic semiconductors, i.e., triaryl and tetraryl lactones (figure 2). The polyaryl lactones, ladder-type oligomers, targeted in this study consist of three or more aromatic ring systems joined by axial bonds and lactone linkages along the length of the molecules. Conjugated oligomers are attractive replacements for the more conventional inorganic semiconducting materials. The extended p-systems of the oligomers give rise to their semiconductive properties and the ability to “tweak” the chemical structure of oligomers provides great control over the conductive, thermal, oxidative and mechanical properties of the materials. We will utilize palladium-mediated intramolecular, aryl-aryl coupling to create the axial bonds in the molecules.
Figure 2: Triaryl and Tetraryl targets
- CHEM 3341 Organic Chemistry I
- CHEM 3342 Organic Chemistry II
- CHEM 4331 Advanced Organic Chemistry I
- Truran, George A.; Aiken, Karelle S.; Fleming, Thomas R.; Webb, Peter J.; Markgraf, J. Hodge, Solid phase organic synthesis and combinatorial chemistry: A laboratory preparation of oligopeptides J. Chem. Ed. 2002, 79(1), 85-86.
Last updated: 7/1/2013