Research with Dr. O'Brien

Teaching Philosophy

My teaching philosophy is three-fold:

1) the use of problem solving and critical thinking in the laboratory,
2) the development of a sense of ownership for one's work through accountability and not through entitlement, and
3) fairness and timeliness with the students. 

The first element of my teaching philosophy focuses on providing opportunities for the students to use their brains to critically think about the objectives of each experiment and to be thought of as problem solvers.  Once they graduate from school, their careers will focus on solving problems in whatever field they chose.  The second element involves the student taking ownership for their work in the laboratory and the fact that they have to earn their grade through performance of the said tasks within the experiment.  The students must be held accountable for their actions and the sense of entitlement must be removed.  The third element of my teaching philosophy applies to fairness and timeliness with regard to interactions with the students.  As mentioned in the second element, I'm accountable to the student as an instructor with regard to fairness in grading of the lab reports and how I interact with each student during the course of the experiment.  I try to communicate realistic and achievable expectations during the experiment.  The goal is to prepare the student for the classroom and beyond.

Research

Our research efforts, in collaboration with Dr. Davis’s group, have focused on the development of novel classes of ionic liquids utilizing the thiol-ene and thiol-yne photochemical reactions.  These new molecules incorporate the sulfur atom into the alkyl side chain of the imidazolium, ammonium, and pyridinium cationic frameworks.  The incorporation of the sulfur atom has profound effects upon the melting points of these ionic liquids as compared with their saturated and unsaturated counterparts. In addition, a variety of functional groups and branching may be incorporated into the side chains of these ionic liquids employing the thiol-ene and thiol-yne reactions as a synthetic tool. These new ionic liquids are attractive as advanced materials for lubricants, phase transfer reagents, freezing points depressants, heat transfer fluids, and materials for separations.

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Recent Publications & Collaborations

Mirjafari, A., O’Brien, R.A, West, K.N., Davis, Jr., James, “Solvent Effect on the Pathway and Regioselectivity of Thiol-ene Click Reaction: Novel Synthesis of Branched Lipid-Inspired Ionic Liquids.” (Manuscript in preparation)

O’Brien, R.A., Hamade, F.A., Mirjafari, A., West, K.N., & Davis, Jr., J.H. Thiol-ene Chemistry with Vinylphosphonic Acids: A new strategy for the Synthesis of Substituted Phosphonic Acids and their Derivatives. Poster presented at the 20th Annual University of South Alabama Research Forum (2013).

O’Brien, R.A., Wheeler-West, C., Hollingsworth, B.E., Mirjafari, A., Mobarrez, N., West, K.N., & Davis, Jr. J.H. Synthesis of Novel Tetraalkylammonium Bromides and their Derivatives as a new class of Phase Transfer Catalysts. Poster presented at the 20th Annual University of South Alabama Research Forum (2013).

O’Brien,R.A., Wheeler West, C., Hollingsworth, B.E.,  Stenson, A.C., Henderson, B.,  Mirjafari, A., Mobarrez, N., West, K.N.  Mattson, K.M., Salter, E.A., Wierzbicki, A., Davis, Jr., J.H. “A Simple and Rapid Route to Novel Tetra(4-thiaalkyl)ammonium Bromides”, RSC Adv., 2013, 3, 24612.

Cassity, C.G., Mirjafari, A., Mobarrez, N., Strickland, K.J., O'Brien, R.A., Davis, Jr., J.H. "Ionic liquids of superior thermal stability" Chem. Commun. 2013, 49, 7590. (Cited in Chemical & Engineering News, August 12, 2013, Volume 91, Number 32, page 27, “Ionic Liquids at High Temps”)

O’Brien, R.A., Mirjafari, A., Murray, S. M., Mattson, K. M., Stenson, A. C., West, K. N., Davis, Jr., J. H.  "Sulfur as an unsaturation ‘effect isostere’ in lipidic materials: Tm lowering in lipid- inspired ionic liquids" (Manuscript in preparation)

Murray, S., Zimlich, T., Mirjafari, A., O'Brien, R.A., Davis, Jr., J. H., West, K. "Thermophysical Properties of Imidazolium-based Lipidic Ionic Liquids." Journal of Chemistry and Engineering Data 2013, 58(6), 1516.

Kwan, M-L, Mirjafari, A., McCabe, J.R., O'Brien, R.A., Essi IV, D.F., Baum, L., West, K.N., Davis, Jr., J.H. "Synthesis and thermophysical properties of ionic liquids: Cyclopropyl moieties versus olefins as Tm-reducing elements in lipid-inspired ionic liquids" Tetrahedron Lett. 2012, 54, 12-14.

Mirjafari, A., O'Brien, R.A., Murray, S. M., Mattson, K. M., Mobarrez, N., West, K. N., & Davis, Jr., J. H. "Lipid-Inspired Ionic Liquids Containing Long-Chain Appendages: Novel Class of Biomaterials with Attractive Properties and Applications." American Chemical Society Ionic Liquids: Science and Applications 2012, 199-216.

Mirjafari, A., Murray, S. M., O’Brien, R.A., Stenson, A. C., West, K. N., Davis, Jr., J. H. "Cation structure and low Tm in lipidic ionic liquids: What can commercial transfection agents teach us?"Chem. Commun. 2012, 48, 7522.

Mirjafari, A., Murray, S. M., O'Brien, R.A., West, K. N., & Davis, J. H. Jr. (2012) Cationic lipids (transfection) as design tutors: insights into structure-property relationships in lipidic ionic liquids. Poster presented at the 243rd ACS National Meeting Division of Industrial and Engineering Chemistry I&EC, March 25-29, 2012, San Diego, CA.

Mirjafari, A., Reynolds, R. A., Mobarrez, N., O'Brien, R.A., West, K. N. & Davis, Jr., J. H. (2012) Functionalized sucrose esters of fatty acids: Synthesis of novel biobased compounds using SEFOSE® by oxymercuration-demercuration reactions. Poster presented at the 243rd ACS National Meeting, Division of Cellulose and Renewable Materials (CELL) and Sci-Mix, March 25-29, 2012, San Diego, CA.

Mirjafari, A., O'Brien, R.A., Murray, S. M., Thigpen, A. S., West, K. N., & Davis, Jr., J. H. (2012) Thiol-ene click reactions as an efficient approach to synthesize structurally diverse pyridinium-based ionic liquids. Poster presented at the 243rd ACS National Meeting Division of Industrial and Engineering Chemistry I&EC, March 25-29, 2012, San Diego, CA.

O'Brien, R.A., Mirjafari, A., Mattson, K. M., Murray, S. M., West, K. N., & Davis, Jr., J. H. (2012) Sulfur as an unsaturation ‘effect isostere’ in lipidic materials: Tm lowering in lipid-inspired ionic liquids and fatty acids. Poster presented at the 243rd ACS National Meeting Division of Industrial and Engineering Chemistry I&EC, March 25-29, 2012, San Diego, CA.

West, K.N., Al-Hashem, A., O’Brien, R.A., Mirjafari, A., Davis, Jr., J.H. (2012) Thermophysical Characterization of Lipidic Ionic Liquids. Paper presented at the 12th AIChE Annual Meeting, Minneapolis, MN.

West, C.W., O’Brien, R.A., Davis, Jr., J.H., Mirjafari, A. (2012) Kinetic Evaluation of Novel Ammonium Phase Transfer Catalysts. Paper presented at the 12th AIChE Annual Meeting, Minneapolis, MN.

O'Brien, R.A., Mirjafari, A., Mobarrez, N., Murray, S.M., Salter, E.A., Weirzbicki, A., West, K.N. & Davis Jr., J.H. Sulfur as an unsaturation 'effect isostere' in lipidic materials: Tm lowering in lipid-inspired ionic liquids and fatty acids. Poster presented at the 19th Annual University of South Alabama Research Forum (2012).

Mirjafari, A., O'Brien, R.A., Mobarrez, N., Murray, S.M., Thigpen, A.S., West, K.N. & Davis Jr., J.H. Thiol-ene "click" reactions as an efficient approach to synthesize structurally diverse pyridinium-based ionic liquids. Poster presented at the 19th Annual University of South Alabama Research Forum (2012).

Mobarrez, N., Mirjafari, A., O'Brien, R.A., West, K.N. & Davis Jr., J.H. Thiol-yne coupling reactions as a green protocol to synthesize structurally diverse ionic liquids. Poster presented at the 19th Annual University of South Alabama Research Forum (2012).

O'Brien, R.A., Mattson, K.M., Mirjafari, A., Murray, S.M., West, K.N. & Davis Jr., J.H. Preparation of Lipid-Inspired Ionic Liquids via Thiol-ene Reaction and the Study of the Sulfur Position in a C18 Alkyl Appendage on the Melting Points. Poster presented at the 4thCongress of Ionic Liquids (2011).

Murray, S.M., Mirjafari, A., O'Brien, R.A., West, K.N. & Davis Jr., J.H. Thermophysical Characterization of Novel Lipid-Inspired Ionic Liquids. Poster presented at the 4th Congress of Ionic Liquids (2011).

Mirjafari, A., O'Brien, R.A., Murray, S.M., West, K.N. & Davis Jr., J.H. Thiol-ene Coupling Reaction of an Oleyl-based Precursor: Synthesis of Novel Lipid-inspired Ionic Liquids. Poster presented at the 4th Congress of Ionic Liquids (2011).

O'Brien, R.A., Mirjafari, A., West, K.N. & Davis Jr., J.H. Functionalized Ionic Liquids with Highly Polar Polyhydroxylated Appendages and their Rapid Synthesis via Thiol-ene Click Chemistry. Poster presented at the 4th Congress of Ionic Liquids (2011).

O'Brien, R.A., Mattson, K.M., Mirjafari, A., Murray, S.M., West, K.N. & Davis Jr., J.H. Synthesis of Lipidlike Ionic Liquids with Diverse Appendages via the Thiol-ene Reaction. Poster presented at the 4th Congress of Ionic Liquids (2011).

O'Brien, R.A., Mattson, K.M., McDonald, L., Mirjafari, A., Murray, S.M., West, K.N. & Davis Jr., J.H. Thiol-ene Coupling Reactions as a Method to Prepare Functionalized Ionic Liquids. Poster presented at the 4th Congress of Ionic Liquids (2011).

Mirjafari, A., O'Brien, R.A., Murray, S.M., West, K.N. & Davis Jr., J.H. Thiol-yne Coupling Reactions as a Tool to Prepare Structurally Diverse Ionic Liquids. Poster presented at the 4th Congress of Ionic Liquids (2011).

Mirjafari, A., O'Brien, R.A., West, K.N. & Davis Jr., J.H. Transformation of DOTMA and Liposomes into Lipid-based Ionic Liquids. Poster presented at the 4th Congress of Ionic Liquids (2011).

O'Brien, R.A., West, K.N. & Davis Jr., J.H. Functionalized Ionic Liquids with Highly Polar Polyhydroxylated Appendages and their Rapid Synthesis via Thiol-ene Click Chemistry. Presented at the 18th Annual University of South Alabama Research Forum (2011).

Murray, S.M., Mattson, K.M., O'Brien, R.A., West, K.N. & Davis Jr., J.H. Synthesis and Characterization of Lipid-Inspired Ionic Liquids. Poster presented at the 18th Annual University of South Alabama Research Forum (2011).

Dorman, S. C., O'Brien, R.A., Lewis, A., Salter, E. A., Wierzbicki, A., Hixon, P. W., Sykora, R. E., Mirjafari, A., Davis, Jr., J. H. "A new building block for electroactive organic materials? Synthesis, cyclic voltammetry,  single crystal X-ray structure, and DFT treatment of a unique boron-based viologen", Chem. Commun. 2011, 47, 9072.

O'Brien, R.A., Mirjafari, A., Jajam, V., Capley, E. N., Stenson, A. C., West, K. N., Davis, Jr., J. H. "Functionalized ionic liquids with highly polar polyhydroxylated appendages and their rapid synthesis via thiol-ene click chemistry" Tetrahedron Lett. 2011, 52, 5173.

Mirjafari, A., Mobarrez, N., Davis, Jr., J. H., O'Brien, R.A., Noei, J. "Microwave-promoted one-pot conversion of alcohols to oximes using 1-methylimidazolium nitrate, [Hmim][NO3], as a green promoter and medium" C. R. Chimie 2011, 14(12), 1065.

Murray, S. M.; O’Brien, R.A.; Mattson, K. M.; Ceccarelli, C.; Sykora, R. E.; West, K. N.; Davis, Jr., J. H. "The Fluid-Mosaic Model, Homeoviscous Adaptation, and Ionic Liquids: Dramatic Lowering of the Melting Point by Side-Chain Unsaturation” Angew. Chem. Intl., 2010, 49, 2755.  (Cited in Chemical & Engineering News, March 15, 2010, Volume 88, Number 11, page 11, “New Chains for Ionic Liquids”.)

Soutullo, M. D.; O’Brien, R.A.; Gaines, K. E.; Davis, Jr., J. H. “Constitutional Dynamic Systems of Ionic and Molecular Liquids” Chem. Commun. 2009, 2529-2531.

Professional Development
  • 2011 “Top Prof” from the Azalea Chapter of Mortar Board, University of South Alabama
  • Chemistry Department General Education Sub Committee
  • Chemistry Instrumentation Coordinator (NMR, UV-Vis, AA, CEM Microwaves, Fluorescence and Electrochemical)