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Kenneth J. Shea

Professor, Chemistry
School of Physical Sciences

PH.D., Pennsylvania State University, 1973


B.S. 1968, University of Toledo

Phone: (949) 824-5844
Fax: (949) 824-2210
Email: kjshea@uci.edu

University of California, Irvine
5042D Frederick Reines Hall
Mail Code: 2025
Irvine, CA 92697

picture of Kenneth J. Shea

Research
Interests
Synthetic Organic, Polymer and Materials Chemistry
   
URL Shea Research Group
   
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
   
Appointments Postdoctoral Fellow, California Institute of
Technology
   
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.

   
Available Technologies
Publications 2010


  • "Synthetic Polymer Nanoparticles with Antibody-Like Affinity for a Hydrophilic Peptide"  Zhiyang Zeng, Yu Hoshino, Andy Rodriguez, Hoseong Yoo, and Kenneth J. Shea, ACS Nano, 2010, 4, 199-204.

  • "As Synthesized" Nanoparticles Recognize, Neutralize and Remove a Toxic Peptide in vivo", Yu Hoshino, Hiroyuki Koide, Takeo Urakami, Hiroaki Kanawaza, Takashi Kodama, Zhiyang Zeng, Naoto Oku, and Kenneth J. Shea, J. Am. Chem. Soc. 2010, 132, 6644-6645.

  • "The Living Polymerization of Ylides". a Chapter in "Complex Macromolecular Architectures: Synthesis, Characterization, and Self-Assembly", Jun Luo and Kenneth J. Shea, John Wiley & Sons, 2010.

  • "Deciphering the Chemical Basis of Nestmate Recognition" Ellen van Wilgenburg, Robert Sulc, Kenneth J. Shea, Miriam Brandt, and Neil D.Tsutsui. Journal of Chemical Ecology, 2010, 36, in press.

  • "Polyhomologation; A Living C1 Polymerization" Jun Luo and Kenneth J. Shea, Accounts of Chemical Research, 2010, 43, in press.

  • "Uniform, Spherical Bridged Polysilsesquioxane Nano- and Microparticles",  Li-Chih Hu, Mariya Khiterer, Shing-Jong Huang, Jerry Chun Chung Chan, Joe Davey, and  Kenneth J. Shea, Chemistry of Materials, 2010, 22, in press.

   
  2009

  • "New Architectures in Hydrogen Bond Catalysis", A. A. Rodriguez, H. Yoo, J. W. Ziller, K. J. Shea, Tetrahedron Letters, 2009, 50, 6830-6833.

  • "Synthesis of the Bicyclic Welwitindolinone Core via an Alkylation/Cyclization Cascade Reaction", J. A. Brailsford, R. Lauchli, K. J. Shea, Organic Letters, 2009, 11, 5330-5333.

  • "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.

  • "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, 1562– 1568.

  • "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, 71.

  • "Asymmeric bis-Boranes as Bidentate Catalysts for Carbonyl Substrates" Andrew A. Rodriguez, Carrie Zhao, and Kenneth J. Shea, Organic Letters, 2009, 11, 713-715.

  • "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.

  • "Squeezing of Ionic Liquids Through Nanopores", Matthew Davenport, Andrew Rodriguez, Ken Shea, Zuzanna S. Siwy, Nano Letters, 2009, 9, 2125-2128.
   
  2008

  • "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.

  • "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/.

  • "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.

  • "Photoresponsive Hybrid Materials: Synthesis and Characterization of Coumarin-Dimer-Bridged Polysilsesquioxanes", Lihua Zhao,  Douglas A. Loy,  Kenneth J. Shea, Chem. Mater. 2008, 20, 1870–1876.

   
  2007

  • "Screening of 5-HT1A Receptor Antagonists using Molecularly Imprinted Polymers", Naphtali A. O’Connor, David A. Paisner, Donna Huryn and Kenneth J. Shea, J. Am. Chem. Soc. 2007, 128, 1680-1689.

  • "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.

  • "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.

  • "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.

   
  2006

  • "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. 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 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.

  • "Selective Protein Capture by Epitope Imprinting", Hidekazu Nishino, Chin-Shiou Huang, and Kenneth J. Shea, Angew. Chem. Int. Ed. 2006, 45, 2392-2396.

  • "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.

  • "Photo-deformable Spherical Hybrid Nanoparticles" Lihua Zhao, Douglas A. Loy, Kenneth J. Shea. J. Am. Chem. Soc. 2006, 128, 14250-14251.

   
  2005

  • "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.

  • "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-?-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.

   
  2004

  • "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.

  • "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.

  • "Bridged Polysilsesquioxanes.  Molecular – Engineering Nanostructured Hybrid Organic-Inorganic Materials."  Kenneth J. Shea, J. Moreau, Doug A. Loy, R.J.P. Corriu, B. Bour, a chapter in "Functional Hybrid Materials", 2004, 50-85 Wiley Interscience, New York.

  • "Molecularly Imprinted Polymers," B. Hart and K. J. Shea in Encyclopedia of Polymer Science and Technology, John Wiley & Sons, New York,  2004

  • "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.

  • "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.

  • "Thermal Stability and Kinetics of Ylide-Borane Complexes", Jonathan M. Stoddard and Kenneth J. Shea, Thermochimica Acta, 2004, 424, 149-155.

  • "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.

  • "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.

   
   
Link to this profile http://www.faculty.uci.edu/profile.cfm?faculty_id=2971
   
Last updated 08/11/2010