Kenneth J. SheaProfessor, Chemistry |
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Research Interests |
Synthetic Organic, Polymer and Materials Chemistry | |
| URL | Shea Research Group | |
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Academic Distinctions |
Regents Faculty Fellow School of Physical Sciences Distinguished Teaching Award NIH Senior International Fellow Winston Churchill College Overseas Fellow, Cambridge University Fellow of the American Association for the Advancement of Science Arthur C. Cope Scholar Award |
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| Appointments |
Postdoctoral Fellow, California Institute of Technology |
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Research Abstract |
Organic Synthesis Organic synthesis is the enabling science for many new technologies. We are developing new methods and strategies for synthesizing carbon-carbon bonds. Projects include the use of pericyclic reactions to achieve control of stereochemistry, regiochemistry, and absolute configuration of complex polycyclic skeletons. Novel bridged bicyclics, such as anti-Bredt olefins, frequently serve as key intermediates. Synthetic targets, which include both biologically important natural products and highly strained compounds of theoretical interest, serve to highlight the utility of these new strategies. Currently we are developing new approaches for synthesizing complex heterocycles.  Polymer Chemistry - Materials Science Molecular Imprinting - Molecular imprinting is a general protocol for creating receptor and/or catalytic sites in cross-linked network polymers. We are using molecular imprinting to prepare materials that function as synthetic biological receptors and as artificial cell membranes that mediate the selective transport of complex organic molecules. Imprinted polymers are being developed for their use as surrogates for drug receptors, catalysts, separation media and as the recognition element for chemical sensors. Additional topics include microfabrication of imprinted polymers and the design of imprinted polymers for binding small peptides. The program interfaces polymer and synthetic organic chemistry, as well as materials science and bioorganic chemistry.  Polymer and Material Synthesis - Carbon backbone polymers are the worlds most widely used synthetic materials. We are developing new reactions for the synthesis of carbon backbone polymers. Unlike the traditional methods of polymer synthesis that involve the polymerization of olefins, our method assembles the carbon backbone one carbon at a time. These new living polymerization reactions are being used to synthesize functional carbon backbone polymers, and to create novel polymer topologies such as huge macrocyclic rings.   Material Synthesis - Bridged polysilsesquioxanes are hybrid organic-inorganic materials that are prepared by sol-gel polymerization from monomers that contain a variable organic bridging group and an inorganic oxide precursor. The resulting xerogels and aerogels have physical and mechanical properties that are strongly influenced by the organic bridging group. We are interested in studying the relationship between bulk properties of the material and the molecular building block. Physical properties such as porosity, thermal stability, refractive index, optical clarity, chemical resistance, hydrophobicity, and dielectric constant can be controlled at the molecular level of design. The materials are being evaluated in such diverse applications as "super absorbents" for wastewater remediation, and as processable materials for fabrication of non-linear optical devices. 
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| Publications | "Polymethylene-block-Poly(dimethylsiloxane)-block-Polymethylene Nanoaggregates in Toluene at Room Temperature," Jiandong Wang, J. Hugh Horton, Guojun Liu and Kenneth J. Shea, submitted for publication. | |
| "Functionalized Coumarin Dimers and Their Use as Photoresponsive Building Blocks for Bridged Polysilsesquioxanes," Lihua Zhao, Douglas A. Loy, Kenneth J. Shea, submitted for publication. | ||
| "Synthetic Protein Receptors Based Upon Peptide Epitope Molecular Imprinting," Y. Cao, H. Nishino, C.-S. Huang, and Kenneth J. Shea, submitted for publication. | ||
| "Screening of 5-HT1A Receptor Antagonists using Molecularly Imprinted Polymers," Naphtali A. OConnor, David A. Paisner, Kenneth J. Shea, J. Amer. Chem. Soc, 2006, in press. | ||
| "The BH3-Catalyzed Oligomerization of Ethyl Diazoacetate. The Role of C-Boron Enolates," Jie Bai, Lonnie D. Burke and Kenneth J. Shea, J. Amer. Chem. Soc. 2006, 128, XXXX. | ||
| "A Synthesis of the Welwistatin Core", Ryan Lauchli and Kenneth J. Shea, Organic Letters, 2006, 8, ASAP. | ||
| "Copolymers from a Single Monomer: Synthesis of Poly(methylidene-co- trimethylsilylmethylidene)," Jie Bai and Kenneth J. Shea, Macromolecules, 2006, 39, 7196-7198. | ||
| "Repetitive sp3-sp3 Carbon-Carbon Bond Forming Co-Polymerizations of Primary and Tertiary Ylides. The Synthesis of Substituted Carbon Backbone Polymers. Poly-(cyclopropylidine-co- methylidine)", Robert Sulc, Xian-Zhi Zhou, Kenneth J. Shea. Macromolecules, 2006, 39, 4948-4952. | ||
| "Hybrid Polyelectrolyte Materials for Fuel Cell Applications: Design, Synthesis and Evaluation of Proton-Conducting Bridged Polysilsesquioxanes," Maria Khiterer, Doug Loy, Christopher J. Cornelius, Cy H. Fujimoto, James H. Small, Theresa M. McIntire, Kenneth J. Shea, Chem. Mater. 2006, 18, 3665-3673. | ||
| "Chemically Modified Dansyl Probes. A Fluorescent Diagnostic for Ion and Proton Detection in Solution and in Polymers," N.A. O'Connor, S. T. Sakata, H. Zhu and K. J. Shea, Organic Letters, 2006, 8, 1581-1584. | ||
| "The Reaction of Boranes with TMS diazomethane and Dimethylsulfoxonium Methylide. The Synthesis of Poly(methylene-co-trimethylsilylmethylene) Random Copolymers" by Jie Bai and Kenneth J. Shea, Macrom. Rapid Commun. 2006, 27, 1223-1228. | ||
| "Photo-deformable Spherical Hybrid Nanoparticles," Lihua Zhao, Douglas A. Loy, Kenneth J. Shea. J. Am. Chem. Soc. 2006, 128. 14251-14251. | ||
| "Selective Protein Capture by Epitope Imprinting," Hidekazu Nishino, Chin-Shiou Huang, and Kenneth J. Shea, Angew. Chem. Int. Ed. 2006, 45, 2392-2396. | ||
| "Alternating Droplet Generation And Controlled Dynamic Droplet Fusion in a Microfluidic Device for Cds Nanoparticle Synthesis," L. H. Hung, K.M. Choi, W.Y. Tseng, Y. C. Tan, K. J. Shea, and A. P. Lee , Lab on a Chip, 2006, 6, 174-178. | ||
| "Formulation and Performance of Novel Energetic Nanocomposites and Gas generators Prepared by Sol-Gel Methods." B. J. Clapsaddle, L. Zhao, D. Prentice, M.L. Pantoya, A. E. Gash, J. H. Satcher Jr., K. J. Shea, R. L. Simpson, Proceedings of the 36th Annual Conference of ITC, Karlsruhe, Germany, June 2005. | ||
| "Strategies for the Generation of Molecularly Imprinted Polymeric Nitroxide Catalysts," Christopher D. Anderson, Kenneth J. Shea and Scott D. Rychnovsky, Organic Letters. 2005, 7, 4879-4882. | ||
| "Synthesis and Chemistry of Bridgehead Allylsilanes. Stereoselective Reactions with Aldehydes," Ryan Lauchli, John M. Whitney, Liang Zhu, and Kenneth J. Shea, Organic Letters. 2005, 7, 3913-3916. | ||
| "The Polyhomologation of Triallylborane: Synthesis of a-Vinyl-ω-Functional-Polymethylene by a Living Polymerization," Carl E. Wagner, Andrew Rodriguez, and Kenneth J. Shea, Macromolecules, 2005, 38, 7286-7291. | ||
| "Dual Function Catalysts. Dehydrogenation and Intramolecular Diels-Alder Cycloaddition of N-Hydroxy Formate Esters and Hydroxamic Acids. Evidence for a Ruthenium-Acylnitroso Intermediate," Chun P. Chow and Kenneth J. Shea, J. Am. Chem. Soc. 2005, 127 , 3678-3679. | ||
| "Controlled droplet fusion in microfluidic devices," L.H. Hung, W.Y. Tseng, K.M. Choi, Y.C. Tan, K. J. Shea, A.P. Lee, Micro TAS 2004, Conference Proceedings, Sweden. | ||
| "Molecularly Imprinted Polymers," B. Hart and K.J. Shea in Encyclopedia of Smart Materials, John Wiley & Sons, New York, 2004. | ||
| "Integrated Chemical Systems: The Simultaneous Formation of Hybrid Nanocomposites of Iron Oxide and Organo Silsesquioxanes," Li Zhao, B. J. Clapsaddle, J. H. Satcher, Jr., D.W. Schaefer, K. J. Shea, Chem. Mater., 2005, 17, 1358-1366. | ||
| "The Use of Metal Coordination for Controlling the Microenvironment of Imprinted Polymers," Peter G. Conrad, II, and Kenneth J. Shea, a chapter in Molecularly Imprinted Materials: Science and Technology, Yan, M and Ramstrom, Eds. Marcel Dekker, 2005, 123-180. | ||
| "Effect of pH on the Gelation Time of Hexylene-Bridged Polysilsesquioxanes," D. A. Loy, B. Mather, A. R. Straumanis, C. Baugher, D. A. Schneider, A. Sanchez, and K. J. Shea, Chem. Mater., 2004, 16, 2041-2043. | ||
| "Structure of Arylene-Bridged Polysilsesquioxane Xerogels and Aerogels," D.W. Schaefer, G. Beaucage, D. A. Loy, K. J. Shea, and J.S. Lin, Chem. Mater., 2004, 16, 1402-1410. | ||
| "The Type 2 Intramolecular N-Acylnitroso Diels-Alder Reaction: Scope and Application to the Synthesis of Medium Ring Lactams", Steven M. Sparks, Chun P. Chow, Liang Zhou and Kenneth J. Shea, J. Org. Chem., 2004, 69, 3025-3035. | ||
| "Thermal Stability and Kinetics of Ylide-Borane Complexes", Jonathan M. Stoddard and Kenneth J. Shea, Thermochimica Acta, 2004, 424, 149-155. | ||
| "On The Relative Migratory Aptitudes of Carbon and Heteroatoms in Borate Complexes A Surprising a-thia Effect", Jonathan Stoddard and Kenneth J. Shea, J. C. S. Chem. Commun., 2004, 830-831. | ||
| "Synthesis and First Molecular Structure of a Bis-2-Spiro-1-Boraaddamantance Derivatives", Carl E. Wagner and Kenneth J. Shea, Organic Letters, 2004, 6, 313-316. | ||
| "Preparation of Perhydroisoquinolines via the Intramolecular Diels-Alder Reaction of N-3,5-Hexadienoyl Ethyl Acrylimidates: A Formal Synthesis of (±)-Reserpine", Steven M.Sparks, Arnold J. Gutierrez, and Kenneth J. Shea, J. Org.Chem. 2003, 68, 5274-5285. | ||
| "Functional Molecularly Imprinted Polymer Microstructures Fabricated Using Microstereolithographic Techniques", P.G. Conrad, II, P.T. Nishimura, D. Aherne, B.J. Schwartz, D. Wu, N. Fang, X. Zhang, J. Roberts, and K.J. Shea, Advanced Materials, 2003, 11, 5274-5285. | ||
| "The Polyhomologation of 1-Boraadamantane-THF," C. E. Wagner, J. S. Kim, K. J. Shea, J. Am. Chem. Soc. 2003, 125, 12179-12195 . | ||
| "Progress Toward the Total Synthesis of (+)-Aldosterone: Synthesis of the A-D Rings," Brian R.Bear, Jason S. Parnes, and Kenneth J. Shea, Organic Letters, 2003, 5, 1613. | ||
| "Combinatorial Chemistry and Molecular Imprinting. A Review," D. Batra and K.J. Shea, Current Opinion in Chemical Biology, 2003, 7, 435-442. | ||
| "Synthesis of 1-Boraadamantane Amine Derivatives for Pharmacology Studies in the Treatmeant of Hepatitis C: Binding Small Molecules to the CD 81 Transmembrane Protein," Carl E. Wagner, M.L. Mohler, G.S. Kang, D.D. Miller, Yu-An Chang, E.B. Fleischer and Kenneth J. Shea, J. Med.Chem., 2003, 46, 2823-2833. | ||
| "Diastereoselective Self-Assembly of a Pentacoordiante Siliconate Tetraanionic Molecular Square. A Mechanistic Investigation," Joshua J. Pak, John Greaves, Dianne J. McCord and Kenneth J. Shea, Organometallics, 2002, 21, 3552-3561. | ||
| "Molecular Imprinting for the Recognition of Small N-Terminal Histidine Peptides in Aqueous Solution," Bradley R. Hart and Kenneth J. Shea, Macromolecules, 2002, 35, 6192-6201. | ||
| "The Boron-Catalyzed Polymerizaton of Dimethylsulfoxonium Methylide. A Living Polymethylene Synthesis." B.B. Busch, M.M. Paz, C.L. Staiger, J.M. Stoddard, J. R. Walker, X.Z. Zhou, H. Zhu and K.J. Shea, J. Am. Chem. Soc., 2002, 124, 3636-3646. | ||
| "Bridged Polysilsesquioxanes. Molecular Engineering of Hybrid Organic-Inorganic Materials," K.J. Shea, D.A. Loy, MRS Bulletin, 2001, 26, 368. | ||
| "A Mechanistic Investigation of Gelation. The Sol-Gel Polymerization of Bridged Silsesquioxane Monomers," K.J. Shea, D.A. Loy, Accts. of Chemical Research, 2001, 34, 707-716. | ||
| "Synthetic Peptide Receptors. Molecularly Imprinted Polymers (MIP's) for the Recognition of Peptides Using Peptide-Metal Interactions," Bradley R. Hart and K.J. Shea, J. Am. Chem. Soc., 2001, 123, 2072. | ||
| "The Type 2 Intramolecular Diels-Alder Reaction' Synthesis and Chemistry of Bridgehead Olefins," B.R. Bear, S.M. Sparks, and K.J. Shea, Angew Chem. Int. Ed. Eng. 2001, 40, 820-849. | ||
| Link to this profile | http://www.faculty.uci.edu/profile.cfm?faculty_id=2971 | |
| Last updated | 04/27/2007 | |
