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Shih-Yuan Liu

Assistant Professor — Organic, Organometallic & Inorganic Chemistry

1st Diploma, Vienna University of Technology, 1997. Ph.D., Massachusetts Institute of Technology, 2003 (Gregory C. Fu). Postdoctoral: Massachusetts Institute of Technology, 2003-06 (Daniel G. Nocera). At Oregon since 2006.

Research Interests:

We are engaged in synthetic organic/organometallic chemistry with emphasis on developing molecules of importance in biomedical research and materials science.

1) We are interested in the development of B–N-containing heterocycles, namely 1,2-dihydro-1,2-azaborines. These are structures that are isoelectronic and isostructural to benzene. Benzene, the epitome of aromatic compounds, has played a pivotal role in our fundamental understanding of the concept of aromaticity. In addition to this educational value, the chemistry and applications of benzene derivatives have become ubiquitous in our daily lives (e.g., plastics, drugs, etc.).

We aim to exploit the unique properties of 1,2-dihydro-1,2-azaborines and investigate their potential as benzene surrogates in materials and biomedical research. Our approach combines the broad utility of arenes with the unique elemental features of boron. Areas of exploration include organic synthesis, optoelectronic materials, catalysis, drug discovery, and cancer therapy. One particular focus of our research is the development of these BN-containing heterocycles as efficient hydrogen storage materials.

2) We are investigating rearrangement-based methodologies for the synthesis of arene and carbocyclic nucleoside derivatives. These classes of molecules play important roles in organic and pharmaceutical chemistry. The salient feature of our method is that both families of molecules can be generated from a single common structural motif depending on the judicious choice of reaction parameters. Our studies have unraveled the dichotomy of this interesting rearrangement process, and we are pursuing the application of our methodology to the synthesis biologically active molecules.

We are skilled in a variety of experimental techniques commonly applied in synthetic organic/organometallic chemistry, e.g., air-free Schlenk line and glovebox techniques for the preparation of our compounds, and X-Ray, NMR, MS, IR, UV-vis, HPLC, GC, electrochemistry for their characterization.

Publications:

8. Tanjaroon, C.; Daly, A.; Marwitz, A. J. V.; Liu, S.-Y.; Kukolich, S. G. “Microwave measurements and ab-initio calculations of structural and electronic properties of N-Et-1,2-azaborine” J. Chem. Phys., accepted.

7. Marwitz, A. J. V.; McClintock, S. P.; Zakharov, L. N.; Liu, S.-Y. “BN benzonitrile: an electron-deficient 1,2-dihydro-1,2-azaborine featuring linkage isomerism” Chem. Commun. 2010, 46, DOI:10.1039/B919632C.

6. Liu, L.; Marwitz, A. J. V.; Matthews, B. W.; Liu, S.-Y. “Boron Mimics: 1,2-Dihydro-1,2-azaborines Bind inside a Non-polar Cavity of T4 Lysozyme” Angew. Chem. Int. Ed. 2009, 48, 6817-6819.

5. Lamm, A. N.; Liu, S.-Y. “How Stable Are 1,2-Dihydro-1,2-azaborines toward water and oxygen?” Mol. Biosyst. 2009, 5, 1303-1305.

4. Marwitz, A. J. V.; Matus, M. H.; Zakharov, L. N.; Dixon, D. A.; Liu, S.-Y. “A Hybrid Organic/Inorganic Benzene” Angew. Chem. Int. Ed. 2009, 48, 973-977. Selected by the editors as a “Hot Paper”. Highlighted in Chemical & Engineering News (C&EN) (2009, January 5, page 11), and in Nature 2009, 457, 239.

3. Glass, A. C.; Morris, B. B.; Zakharov, L. N.; Liu, S.-Y. “Synthesis of Substituted Naphthalenes via a Catalytic Ring-Expansion Rearrangement” Org. Lett. 2008, 10, 4855-4857.

2. Abbey, E. R.; Zakharov, L. N.; Liu, S.-Y. “Crystal Clear Structural Evidence for Electron Delocalization in 1,2-Dihydro-1,2-azaborines” J. Am. Chem. Soc. 2008, 130, 7250-7252. Highlighted in Chemical & Engineering News (C&EN) (2008, June 16, page 12).

1. Marwitz, A. J. V.; Abbey, E. R.; Jenkins, J. T. ; Zakharov, L. N.; Liu, S.-Y. “Diversity through Isosterism: The Case of Boron-Substituted 1,2-Dihydro-1,2-azaborines” Org. Lett. 2007, 9, 4905-4908.

To Contact Dr. Liu:
lsy@uoregon.edu

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