University of South Dakota

Organic Chemistry, Advanced Organic Chemistry, Electrochemistry, Spectroscopic Analysis

My research is focused on the synthesis of two classes of molecules: functional organic materials with special optical and electronic properties, and biologically relevant small organic molecules. The aim of my research is to provide tools for, and insights into two technologically important problems: energy conversion and drug development. One of our strategies is to utilize the unique properties of organofluorine compounds as a toolbox for organic synthesis and to prepare probes of biological function. A unique element to my research will be the development and utilization of new fluoroorganic chemistry. The research program provides training for students in the fields of synthetic organic chemistry, fluorine chemistry, optical and electronic materials chemistry, and bioorganic chemistry. A student/postdoc working in my research group will gain practical experience in multi-step synthesis, modern separation and characterization techniques, air-sensitive techniques, modern electrochemical techniques including digital simulation and spectroelectrochemistry, and computational methods (e.g., ab initio, DFT, MP2).

• Ph D, Chemistry, Jilin University, 1996
• BS, Chemistry, Jilin University, 1990

• Sun, H., Wei, Q., Polyfluorinated Electrolyte Solutions and Additives for High Voltage Non-Flammable Lithium Batteries, ECS Transaction, p. Accepted.
• Biffinger, J., Sun, H., DiMagno, S. G., Fluorinated Porphyrins and Corroles: Synthesis, Electrochemistry, and Applications, Fluorine in Heterocyclic Chemistry, p. Accepted.
• Sun, H., Putta, A., Billion, M., (2012), Arene Trifluoromethylation: An Effective Strategy to Obtain Air-Stable n-Type Organic Semiconductors with Tunable Optoelectronic and Electron Transfer Properties, J. Phys. Chem. A , vol. 116, pp. 8015-8022 .
• Sun, H., Tottempudi, U. K., Mottishaw, J. D., Basa, . N., Putta, A., Sykes, A., (2012), Strengthening p-p Interactions While Suppressing Csp2-H•••p (T-Shaped) Interactions via Perfluoroalkylation: A Crystallographic and Computational Study That Supports the Beneficial Formation of 1-D p-p Stacked Aromatic Materials, Cryst. Growth Des. , vol. 12, pp. 5655-5662.
• Sun, H., Putta, A., Kloster, J. P., Tottempudi, U. K., (2012), Unexpected photostability improvement of aromatics in polyfluorinated solvents. , Chem. Commun. (Cambridge, U. K.), vol. 48, pp. 12085-12087.
• Sun, H., (2011), Fluorinated Aromatic Compounds and Their Preparation and Use in Optoelectronics, PCT Int. Appl., WO 2011022678 A1 20110224..
• Biffinger, J. C., Uppaluri, S., Sun, H., DiMagno, S. G., (2011), Ligand Fluorination to Optimize Preferential Oxidation of Carbon Monoxide by Water-Soluble Rhodium Porphyrins , ACS Catalysis , vol. 1, iss. 7, pp. 764-771.
• Sun, H., Koch, A. ., DiMagno, S. G., (2009), Rapid Preparation of Fluorinated Aromatic Heterocycles, ACS symposium series, ACS symposium series, vol. 1003, pp. 85-104 .
• Sun, H., Wang, B., DiMagno, S. G., (2008), A method for detecting water in organic solvents, Org. Lett. , vol. 10, pp. 4413-4416.
• Sun, H., DiMagno, S. G., (2007), Fluoride relay: a new concept for rapid preparation of anhydrous nucleophilic fluoride salts from KF, Chem. Commun. , p. 528–529.
• Sun, H., DiMagno, S. G., (2006), Room-Temperature Nucleophilic Aromatic Fluorination: Experimental and Theoretical Studies, Angew. Chem. Int. Ed. , vol. 45, p. 2720–2725.
• Sun, H., DiMagno, S. G., (2005), Anhydrous Tetrabutylammonium Fluoride, J. Am. Chem. Soc. , vol. 127, p. 2050–2051.
• Sun, H., Smirnov , V. V., DiMagno, S. G., (2003), Slow Electron Transfer Rates for Fluorinated Cobalt Porphyrins: Electronic and Conformational Factors Modulating Metalloporphyrin ET, Inorg. Chem. , vol. 42, p. 6032–6040.

• Sun, H. (2013, January). Perfluoroalkylation strengthening lamellar p–p stacked structure in n-type organic semiconductor materials: Coherent enhancement of p–p and Csp3-FF-Csp3 interactions. Presented at the 21th winter fluorine conference.
• Sun, H., Wei, Q. (2012, October). Polyfluorinated electrolyte solutions and additives for high voltage non-flammable lithium batteries. Presented at the 222th ECS national meeting.
• Hoefelmeyer, J., Shende, R., Smirnova, A., Puszynski, J., Fong, H., Ahrenkiel, P., Koodali, R., Sereda, G., Kilin, D., Sun, H., Wang, Z., He, H. (2012, April). South Dakota Catalysis Group 12-80. Presented at the 97th Annual Meeting of the South Dakota Academy of Science, Vermillion, SD.
• Sun, H. (2011, August). Effects of direct ring fluorination and perfluoroalkylation on optical and electronic properties of aromatics . Presented at the 242nd ACS National Meeting, Denver, CO, United States.
• Sun, H., Tottempudi, U. K., Yang, C. (2011, August). Synthesis, characterization, and proton affinity of electron deficient phenanthrolines . Presented at the 242nd ACS National Meeting, Denver, CO, United States.
• Sun, H., Putta, A., Kloster, J., Billion, M., Mottishaw, J. (2011, January). Improve photostability of organic semiconductor materials via perfluoroalkylation. Presented at the 20th Winter Fluorine Conference, St. Pete Beach, FL, United States.
• Sun, H., Billion, M. (2010, August). Tuning optical and electronic properties of arene-based organic semiconductors via perfluoroalkylation. Presented at the 240th ACS National Meeting, Boston, MA, United States, August 22-26, 2010 (2010).
• Sun, H., Putta, A., Kloster, J. (2010, August). Synthesis of air-stable, moisture-resistant, and tunable perfluoroalkylated arenes for optoelectronics. Presented at the 240th ACS National Meeting, , Boston, MA, United States.