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. Organic synthesis is the enabling science for many new technologies. We are developing new methods and strategies for the formation of 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 include biologically important natural products that include N-methyl welwistatin and (-)-stenine. We are also developing new bis-Lewis acids as potent catalysts for a variety of synthetic transformations.  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 | "Synthesis of the Bicyclic Welwitindolinone Core via an Alkylation/Cyclization Cascade Reaction", J. A. Brailsford, R. Lauchli, K. J. Shea, Organic Letters, 2009, 11, XXXX. | |
| "The Scent of Supercolonies: The Discovery, Synthesis and Behavioral Verification of Ant Colony Recognition Cues", Miriam Brandt, Ellen van Wilgenburg, Robert Sulc, Kenneth J. Shea and Neil D.Tsutsui, Submitted for Publication. | ||
| "Squeezing of Ionic Liquids Through Nanopores", Matthew Davenport, Andrew Rodriguez, K. Shea, Z. S. Siwy, Nano Letters, 2009, 9, 2125-2128. | ||
| "High Contrast Solid-State Electrochromic Devices of Viologen-bridged Polysilsesquioxane Nanoparticles Fabricated by Layer-by-Layer Assembly" Vaibhav Jain, Mariya Khiterer, Reza Montazami, Hank Yochum, Kenneth Shea, Randy Heflin, Applied Materials & Interfaces, 2009, 1, 83-89. | ||
| "Asymmeric bis-Boranes as Bidentate Catalysts for Carbonyl Substrates" Andrew A. Rodriguez, Carrie Zhao, and Kenneth J. Shea, Organic Letters, 2009, 11, 713-715. | ||
| "Optical Glass Effectively Generating a Large Acoustic Wave for Diffraction Beam Modulator Applications." Kyung M. Choi, Kenneth J. Shea, J. Phys. Chem. C, 2008, 112, 18173-18177. | ||
| "Peptide Imprinted Polymer Nanoparticles: A Plastic Antibody", Yu Hoshino, Takashi Kodama, Yoshio Okahata, and Kenneth J. Shea, J. Amer. Chem. Soc. 2008, 130, 15242-15243.(Highlighted in Nature, 2008, 456, 248, (20 November) and Technology Review, http://www.technologyreview.com/biomedicine/21603/. | ||
| "Photoresponsive Hybrid Materials: Synthesis and Characterization of Coumarin-Dimer-Bridged Polysilsesquioxanes", Lihua Zhao, Douglas A. Loy, Kenneth J. Shea, Chem. Mater. 2008, 20, 18701876. | ||
| "Enantioselective Synthesis of Bridged Bicyclic Ring Systems" John A. Brailsford, Liang Zhu, Mandy Loo, and Kenneth J. Shea, J. Org. Chem. 2007, 72, 9402-9405. | ||
| "Type 2 Intramolecular N-acylazo Diels-Alder Reaction: Regio- and Stereoselective Synthesis of Bridgehead Bicyclic 1,2-Diazines", Claudia L. Molina, Chun P. Chow, and Kenneth J. Shea, J. Org. Chem. 2007, 72, 6816-6823. | ||
| "Spherical, Monodisperse, Functional Bridged Polysilsesquioxane Nanoparticles" Mariya Khiterer and Kenneth J. Shea, Nano Letters, 2007, 7, 2684-2687. | ||
| "An Approach to the Synthesis of Stenine", Liang Zhu, Mandy Loo, Ryan Lauchli and Kenneth J. Shea, Organic Letters, 2007, 9, 2269-2271. | ||
| "The BH3-Catalyzed Oligomerization of Ethyl Diazoacetate. The Role of C-Boron Enolates" Jie Bai, Lonnie D. Burke and Kenneth J. Shea, J. Am. Chem. Soc. 2007, 129, 4981-4991. | ||
| "Screening of 5-HT1A Receptor Antagonists using Molecularly Imprinted Polymers", Naphtali A. OConnor, David A. Paisner, Donna Huryn and Kenneth J. Shea,J. Am. Chem. Soc. 2007, 128, 1680-1689. | ||
| "A Synthesis of the Welwistatin Core" Ryan Lauchli and Kenneth J. Shea, Organic Letters, 2006, 8, 5287-5289. | ||
| "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. OConnor, S. T. Sakata, H. Zhu and K. J. Shea, Organic Letters, 2006, 8, 1581-1584. | ||
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"The Reaction of Boranes with TMS diazomethane and imethylsulfoxonium Methylide. The Synthesis of Poly(methylene-co-trimethylsilylmethylene) Random Copolymers" by Jie Bai and Kenneth J. Shea, Macrom. Rapid Commun. 2006, 27, 1223-1228. |
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| Selective Protein Capture by Epitope Imprinting, Hidekazu Nishino, Chin-Shiou Huang, and Kenneth J. Shea, Angew. Chem. Int. Ed. 2006, 45, 2392-2396. | ||
| The Scent of Supercolonies: The Discovery, Synthesis and Behavioral Verification of Ant Colony Recognition Cues, Miriam Brandt, Ellen van Wilgenburg, Robert Sulc, Kenneth J. Shea and Neil D.Tsutsui, Submitted for Publication. | ||
| "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. | ||
| "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. | ||
| "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. | ||
| "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. | ||
| "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. | ||
| "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. | ||
| "The Scent of Supercolonies: The Discovery, Synthesis and Behavioral Verification of Ant Colony Recognition Cues", Miriam Brandt, Ellen van Wilgenburg, Robert Sulc, Kenneth J. Shea and Neil D. Tsutsui, BMC Biology, 2009, 7, XXXX. | ||
| "New Architectures in Hydrogen Bond Catalysis", A. A. Rodriguez, H. Yoo, J. W. Ziller, K. J. Shea, Tetrahedron Letters, 2009, 50, XXXX. | ||
| "Molecularly Imprinted Polymers. Synthetic Receptors for Small Molecules, Peptides and Proteins. The Evolution of a Plastic Antibody", Kenneth J. Shea and Yu Hoshino, Med. Chem. News (Japan), 2009, 19, 12-16. | ||
| "Squeezing of Ionic Liquids Through Nanopores", Matthew Davenport, Andrew Rodriguez, Ken Shea, Zuzanna S. Siwy, Nano Letters, 2009, 9, 2125-2128. | ||
| "Design of Synthetic Polymer Nanoparticles that Capture and Neutralize a Toxic Peptide", Yu Hoshino, Takeo Urakami, Takashi Kodama, Hiroyuki Koide, Naoto Oku, Yoshio Okahata and Kenneth J. Shea, Small, 2009, 5, 15621568. | ||
| "Novel endcaps and resins for high-temperature composites" Thomas K. Tsotsis, Kenneth J. Shea, Xiguang Li, Hyman R. Lubowitz, Norman R. Byrd, SAMPE Conference Proceedings, 2008, 53, 145/1-145/11. | ||
| "Polymethylene-block-poly(dimethylsiloxane)-block-polymethylene. Nanoaggregates in Toluene at Room Temperature", Jiandong Wang, J. Hugh Horton, Guojun Liu, Sun-Yeol Lee, Kenneth J. Shea,Polymer, 2007, 48, 4123-4129. | ||
| "Photo-deformable Spherical Hybrid Nanoparticles" Lihua Zhao, Douglas A. Loy, Kenneth J. Shea. J. Am. Chem. Soc. 2006, 128, 14250-14251. | ||
| Link to this profile | http://www.faculty.uci.edu/profile.cfm?faculty_id=2971 | |
| Last updated | 10/10/2009 | |
