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Haoran Sun

Haoran Sun



Pardee Estee Laboratory 315

Phone: (605) 658-6740



Teaching Interests:

Advanced Organic Chemistry, Electrochemistry, Fluorine Chemistry, Organic Chemistry, Spectroscopic Analysis

Research Interests:

The goal of our 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 tools for improving materials properties and function. We welcome talents at all levels--undergraduates, graduates, postdocs, and visiting scholars--to join us in solving energy and medicinal problems faced by our society. Our research program provides comprehensive training for students in the fields of organic, fluorine, and materials chemistries. Aiming to their future success, students working in our group will gain practical experience in multi-step synthesis, separation and characterization techniques for organic compounds, air-sensitive techniques, and modern electrochemistry and computational chemistry techniques. You will find more information about our research on our group webpage at Please feel free to email me if you have any questions.


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


  • MRI: Acquisition of a Dual-Source Single-Crystal X-ray Diffractomter, National Science Foundation. Grant Role: Co-Principal. (2019 - 2022)
  • REU Site: Undergraduate Research in Fluorine Chemistry, NSF. Grant Role: Co-Principal. (2018 - 2021)
  • Center for Fluorinated Functional Materials: from Discovery to Commercialization, SD GOED. Grant Role: Principal. (2017 - 2022)
  • Fluorinated non-flammable electrolytes for high energy-density rechargeable batteries: a key research initiative for NASA's human mission, NASA South Dakota EPSCoR. Grant Role: Principal. (2015 - 2016)
  • CAREER: Rational Design of Perfluoroalkylated N- and S-Containing Heteroaromatics for Engineering High Performance Air-stable OFET Materials with Lamellar pi-pi Stacked Structure, NSF. Grant Role: Principal. (2014 - 2019)
  • High Performance and Durable Lithium-ion Battery for NASA Space Applications, NASA-EPSCoR. Grant Role: Co-Principal. (2014 - 2017)
  • R&D Innovation Proposal: Acquisition of a UV-Vis-NIR Microspectrophotometer for High-Resolution Visualization and Characterization of Advanced Materials, South Dakota Board of Regents. Grant Role: Supporting. (2013 - 2014)
  • Fluorinated Materials for Reliable Energy Conversion, Northern Plain Undergraduate Resenrch Center seed grant. Grant Role: Principal. (2011 - 2011)
  • Spectroelectrochemical and Computational Studies on Interfacial Electron Transfer in Dye-sensitized Solar Cells: renewal, DOE PNNL EMSL. Grant Role: Principal. (2010 - 2011)
  • Perfluoroalkyl- and Perfluoropolyether-based Non-flammable Materials for Reliable Energy Conversion, NPURC (THE NORTHERN PLAINS UNDERGRADUATE RESEARCH CENTER). Grant Role: Principal. (2010 - 2011)
  • Fluorinated Materials for Air-stable and Moisture-resistant Flexible Optoelectronics, DOD Army Research Office. Grant Role: Principal. (2009 - 2013)


Citations listed below are presented in a standardized, modified format for display purposes only. They do not necessarily reflect the preferred style and conventions of the faculty member or discipline.

  • Mao, Siyu, Kramer, Jordan H., and Sun, Haoran. Deoxyfluorination of Carboxylic Acids with KF and Highly Electron-Deficient Fluoroarenes, 6066-6074. Vol. 86, Iss. 9. J. Org. Chem., 2021. (DOI: 10.1021/acs.joc.0c02491)
  • Guiton, Beth S., Stefik, Morgan, Augustyn, Veronica, Banerjee, Sarbajit, Bardeen, Christopher J., Bartlett, Bart M., Li, Jun, López-Mejías, Vilmalí, MacGillivray, Leonard R., Morris, Amanda, Rodriguez, Efrain E., Samia, Anna C., Sun, Haoran, Sutter, Peter, and Talham, Daniel R.. Frontiers in hybrid and interfacial materials chemistry research, 951-964. Vol. 45, Iss. 11. MRS Bulletin, 2020. (DOI: 10.1557/mrs.2020.271)
  • Putta, Anjaneyulu Putta, Sykes, Andrew G., and Sun, Haoran. Perfluoroalkylated anthracene endoperoxide: Synthesis, characterization, crystal structure analysis, and computational insights. Vol. 235. J. Fluorine Chem., 2020. (DOI:
  • Sun, Haoran, and DiMagno, Stephen G.. TBAF Fluorination for Preparing Alkyl Fluorides. In Synthetic Organofluorine Chemistry. Fluorination, edited by Jinbo Hu and Teruo Umemoto . Springer, 2018. (DOI: 10.1007/978-981-10-1855-8_14-1)
  • Sun, Haoran, and Kramer, Jordan. Perfluoroalkylated PAH n-type semiconductors: theory and experiment. In New Forms of Fluorinated Carbons: Fundamentals and Applications: Progress in Fluorine Science Series, 1e, edited by Olga V. Boltalina Tsuyoshi Nakajima. Vol. 2, Iss. 1st Ed.. Elsevier , 2016.
  • Sun, Haoran, BaniKhaled, Mohammad O., Becker, John D., and Koppang, Miles. Perfluoroalkylation of square-planar transition metal complexes: a strategy assemble them into solid state materials with pi - pi stacked lamellar structure, 1869-1878. Vol. 16, Iss. 4. Crystal Growth & Design, 2016. (DOI: 10.1021/acs.cgd.5b01291)
  • Erk, Adam, Mottishaw, Jeff, Kramer, Jordan, Sun, Haoran, and Koppang, Miles. Using ESP Maps to visualize chemical reactivity in Sanger's reagent, 1846-1852. Vol. 92, Iss. 11. Journal of Chemical Education, 2015. (DOI: 10.1021/ed5006344)
  • BaniKhaled, Mohammad ., Mottishaw, Jeffery D., and Sun, Haoran. Steering Power of Perfluoroalkyl Substituents in Crystal Engineering: Tuning the ?-? Distance While Maintaining the Lamellar Packing Motif for Aromatics with Various Sizes of ?-Conjugation, 2235-2242. Vol. 15, Iss. 5 . Cryst. Growth Des., 2015. (DOI: 10.1021/cg501894u)
  • DiMagno, Stephen G., Biffinger, Justin C., and Sun, Haoran. Fluorinated Porphyrins and Corroles: Synthesis, Electrochemistry, and Applications. In Fluorine in Heterocyclic Chemistry, edited by Valentine Nenajdenko, 589-620. Vol. 1.. (DOI: 10.1007/978-3-319-04346-3_14)
  • Mottishaw, Jefferey, Cheng, Hai-Ping, Karasiev, Valentin, Fan, Qi-Hua, Sun, Haoran, and Kilin, Dmitri. Elucidating the role of non-radiative processes in charge transfer of model core-shell Si:SiO2 nanoparticles. In Molecular Physics, 422-429. Vol. 112, Iss. 03-04. London: Molecular Physics, 2014. (DOI: 10.1080/00268976.2013.836606)
  • Putta, Anjaneyulu, Mottishaw, Jeffery D., Wang, Zhihua, and Sun, Haoran. Rational Design of Lamellar ?-? Stacked Organic Crystalline Materials with Short Interplanar Distance, 350-356. Vol. 14, Iss. 1. Crystal Growth & Design, 2014. (DOI: 10.1021/cg401637a)
  • Mottishaw, Jeffery D., Sun, Haoran, and . Effects of Aromatic Trifluoromethylation, Fluorination, and Methylation on Intermolecular ?-? Interactions, 7970-7979. Vol. 117. J. Phys. Chme. A, 2013. (DOI: 10.1021/jp403679x)
  • Wang, Zhihua, Putta, Anjaneyulu, Mottishaw, Jeffery D., Wei, Qiang, Wang, Hua, Sun, Haoran, and . Molecular Origin of Isomerization Effects on Solid State Structures and Optoelectronic Properties: A Comparative Case Study of Isomerically Pure Dicyanomethylene Substituted Fused Dithiophenes, 16759-16768. Vol. 117. J. Phys. Chem. C, 2013. (DOI: 10.1021/jp4033029)
  • Sun, Haoran, and Wei, Qiang. Polyfluorinated Electrolyte Solutions and Additives for High Voltage Non-Flammable Lithium Batteries, 349-354. Vol. 50, Iss. 26. ECS Transaction, 2013.
  • Sun, Haoran, Putta, Anjaneyulu, and Billion, Michael. Arene Trifluoromethylation: An Effective Strategy to Obtain Air-Stable n-Type Organic Semiconductors with Tunable Optoelectronic and Electron Transfer Properties, 8015-8022 . Vol. 116. J. Phys. Chem. A , 2012.
  • Sun, Haoran, Tottempudi, Usha K., Mottishaw, Jeffery D., Basa, Prem N., Putta, Anjaneyulu, and Sykes, Andrew. Strengthening ?-? Interactions While Suppressing Csp2-H•••? (T-Shaped) Interactions via Perfluoroalkylation: A Crystallographic and Computational Study That Supports the Beneficial Formation of 1-D ?-? Stacked Aromatic Materials, 5655-5662. Vol. 12. Cryst. Growth Des. , 2012.
  • Hoefelmeyer, James, Shende, Rajesh, Smirnova, Alevtina, Puszynski, Jan, Fong, Hao, Ahrenkiel, Phil, Koodali, Ranjit T., Sereda, Grigoriy, Kilin, Dmitri, Sun, Haoran, and others. THE SOUTH DAKOTA CATALYSIS GROUP, 194. Vol. 91. Published by the South Dakota Academy of Science, 2012.
  • Sun, Haoran, Putta, Anjaneyulu, Kloster, Justin P., and Tottempudi, Usha K.. Unexpected photostability improvement of aromatics in polyfluorinated solvents., 12085-12087. Vol. 48. Chem. Commun. (Cambridge, U. K.), 2012.
  • Sun, Haoran. Fluorinated Aromatic Compounds and Their Preparation and Use in Optoelectronics. PCT Int. Appl., WO 2011022678 A1 20110224., 2011.
  • Biffinger, Justin C., Uppaluri, ShriHarsha, Sun, Haoran, and DiMagno, Stephen G.. Ligand Fluorination to Optimize Preferential Oxidation of Carbon Monoxide by Water-Soluble Rhodium Porphyrins, 764-771. Vol. 1, Iss. 7. ACS Catalysis , 2011.
  • Sun, Haoran, Koch, A ., and DiMagno, S G.. Rapid Preparation of Fluorinated Aromatic Heterocycles, ACS symposium series, 85-104 . Vol. 1003. ACS symposium series, 2009.
  • Sun, Haoran, Wang, B, and DiMagno, S G.. A method for detecting water in organic solvents, 4413-4416. Vol. 10. Org. Lett. , 2008.
  • Sun, Haoran, and DiMagno, S G.. Fluoride relay: a new concept for rapid preparation of anhydrous nucleophilic fluoride salts from KF, 528-529. Chem. Commun. , 2007.
  • Sun, Haoran, and DiMagno, S G.. Room-Temperature Nucleophilic Aromatic Fluorination: Experimental and Theoretical Studies, 2720-2725. Vol. 45. Angew. Chem. Int. Ed. , 2006.
  • Sun, Haoran, and DiMagno, S G.. Anhydrous Tetrabutylammonium Fluoride, 2050-2051. Vol. 127. J. Am. Chem. Soc. , 2005.
  • Sun, Haoran, Smirnov, V V., and DiMagno, S G.. Slow Electron Transfer Rates for Fluorinated Cobalt Porphyrins: Electronic and Conformational Factors Modulating Metalloporphyrin ET, 6032-6040. Vol. 42. Inorg. Chem. , 2003.
  • Sun, Haoran, Mao, Siyu, and Kramer, Jordan H.. Redox-active fluoropolymer. In Progress in Fluorine Science, edited by Bruno Ameduri and Sergei Fomin.. (DOI:

Awards and Honors:

  • President's Award for Research Excellence: Early-Mid Career Faculty, University of South Dakota, 2014
  • NSF CAREER Award, National Science Foundation, 2014


  • Sun, Haoran. Fluorine in functional materials: From crystal engineering to energy storage. Presented at the 24th Winter Fluorine Conference, Clearwater, FL. (January 2019)
  • Mao, Siyu, Kramer, Jordan H., Sun, Haoran. Perfluoroalkylated conductive polymers as organic cathode materials for lithium batteries. Presented at the 24th Winter Fluorine Conference, Clearwater Beach, FL, United States. (January 2019)
  • Kramer, Jordan H., Mao, Siyu, Sun, Haoran. Perfluoroalkylated electron-?deficient aromatic systems for charge-?transfer complexes and anion-?? interactions. Presented at the 24th Winter Fluorine Conference, Clearwater Beach, FL, United States. (January 2019)
  • Balasingam, Mithira, Guerrero, Paulina, Becker, John, Sun, Haoran, Koppang, Miles D.. Electrochemical reduction of nitro groups: Strategies for LC-?EC analysis of Sanger-?derivatized analytes. Presented at the 53rd Midwest Regional Meeting of the American Chemical Society, Ames, IA, United States. (October 2018)
  • Goeden, Brock, Smith, Lorenzo, Kramer, Jordan H., Mao, Siyu, Balasingam, Mithira, Koppang, Miles D., Sun, Haoran. Synthesis, characterization, and electrochemical properties of Schiff base polymers. Presented at the 53rd Midwest Regional Meeting of the American Chemical Society, Ames, IA, United States. (October 2018)
  • Guerrero, Paulina, , John B., Sun, Haoran, Koppang, Miles. Electrochemical reduction of aromatic nitro compounds: Strategies for LC-EC analysis of Sanger tagged analytes. Presented at the 251st ACS National Meeting & Exposition, San Diego, CA. (March 2016)
  • Sun, Haoran. Steering molecular orientation and strengthening ?-? intermolecular interaction through perfluoroalkylation: Insights for rational design of functional molecular materials. Presented at the 2015 International Chemical Congress of Pacific Basin Societies, Honolulu, HI, USA. (December 14-20, 2015). (December 14, 2015)
  • Sun, Haoran. Weak non-?covalent intermolecular interactions involving perfluoroalkyl substituents: Insights for rational design of molecular assemblies. Presented at the 250th ACS National Meeting & Exposition, Boston, MA, United States, August 16-20, 2015 (2015), ORGN-279. . (August 16, 2015)
  • Sun, Haoran. Engineering Lamellar pi-pi Stacked Structures in Solid State Functional Materials by Perfluoroalkylation. Presented at the 25th MOSSCS, Purdue University, IN, June 19-20, 2015. (June 19, 2015)
  • Sun, Haoran. Engineering lamellar ?-?? stacked organic crystalline materials through perfluoroalkylation. Presented at the 22nd Winter Fluorine Conference, American Chemical Society, Division of Fluorine Chemistry, St. Pete Beach, FL, United States, January 11-16 (2015), SP Winter Fluorine Conference-89.. (January 11, 2015)
  • Sun, Jingyi, Sun, Haoran, Koppang, Miles, Putta, Anjaneyulu, Wang, Zhihua. Electrochemical polymerization of dithienophenazine derivatives:. Presented at the 248th ACS National Meeting & Exposition, San Francisco, CA. (August 2014)
  • Kramer, Jordan H., Erck, Adam R., Koppang, Miles, Sun, Haoran, Putta, Anji, Mottishaw, Jeff D.. Ferrocene tagging of amines: An alternative approach using haloferrocenes. Presented at the 48th Midwest Regional Meeting of the American Chemical Society, Springfield, MO. (October 16, 2013)
  • Sun, Haoran. Perfluoroalkylated supramolecular synthons. Presented at the 48th Midwest Regional Meeting of the American Chemical Society , Springfield, MO, United States,. (October 2013)
  • Sun, Haoran, Mottishaw, J D., Putta, A. A. Effects of aromatic perfluoroalkylation on weak non-covalent intermolecular interactions: Insight for rational design of high performance n-type organic semiconductor materials. Presented at the 246th ACS National Meeting & Exposition, Indianapolis, IN, United States. (September 2013)
  • Mottishaw, J D., Dubey, M, Kilin, D, Fan, Q H., Sun, Haoran. Calculating electronic properties of the Si:SiO2 interface using density functional theory with periodical boundary condition, 2013; pp1-6. Presented at the 2013 IEEE International Conference on Electro/Information Technology (EIT). (May 2013)
  • Sun, Haoran. Perfluoroalkylation strengthening lamellar ?-? stacked structure in n-type organic semiconductor materials: Coherent enhancement of ?-? and Csp3-FF-Csp3 interactions. Presented at the 21th winter fluorine conference. (January 13, 2013)
  • Sun, Haoran, Wei, QIang. Polyfluorinated electrolyte solutions and additives for high voltage non-flammable lithium batteries. Presented at the 222th ECS national meeting. (October 7, 2012)
  • Sun, Haoran. 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. (August 2011)
  • Sun, Haoran, Tottempudi, Usha K., Yang, Changying. Synthesis, characterization, and proton affinity of electron deficient phenanthrolines. Presented at the 242nd ACS National Meeting, Denver, CO, United States. (August 2011)
  • Sun, Haoran, Putta, Anjaneyulu, Kloster, Justin, Billion, Michael, Mottishaw, Jeffrey. Improve photostability of organic semiconductor materials via perfluoroalkylation. Presented at the 20th Winter Fluorine Conference, St. Pete Beach, FL, United States. (January 13, 2011)
  • Sun, Haoran, Billion, Michael. 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). (August 25, 2010)
  • Sun, Haoran, Putta, Anjaneyulu, Kloster, Justin. Synthesis of air-stable, moisture-resistant, and tunable perfluoroalkylated arenes for optoelectronics. Presented at the 240th ACS National Meeting, , Boston, MA, United States. (August 24, 2010)