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Current Activities

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Our research is concerned with the chemistry of both organic and organometallic polyfunctional Lewis acids. While an important component of our work deals with the synthesis of new examples of such polyfunctional Lewis acids, it is our ultimate intent to harness and utilize the cooperative effects occurring in such systems for the discovery of unusual structures, bonding modes, supramolecules and reactivities. Our research efforts present important ramifications in the domain of molecular recognition, supramolecular materials and catalysis.

Synthesis: Organic and organometallic synthesis lies at the focal point of our program. We strive to discover high yield synthetic routes for the preparation of both organic and organometallic polyfunctional Lewis acids. These efforts have allowed us to prepare a variety of bidentate and tridentate Lewis acids in which the electrophilic sites are simple carbocations or main-group elements such as mercury(II) and boron(III).

Bonding: In an effort to broaden our fundamental understanding of bonding interactions, we study atypical bonding situations that might arise in the chemistry of polyfunctional Lewis acids. While we have been interested in the formation of radicals featuring one-electron s-bonds, some of our current efforts are devoted to the synthesis of fluoronium ions.

Molecular recognition: Some of these polyfunctional Lewis acids act as polytopic receptors for anions. The significance of this research relates to the discovery of new molecular recognition units for sensory application. For example, we have recently demonstrated that boron-based bidentate Lewis acids can be used as selective colorimetric sensors for fluoride ions. Taking into account the importance of fluoride in the treatment of osteoporosis and in dental care, such sensors may find biomedical applications.

Supramolecular materials: In addition to discovering receptors for small organic molecules including diazines, ketones, aldehydes, oxiranes, and phosphonates, we have also found that trimeric perfluoro-ortho-phenylene mercury, a tridentate Lewis acid, is able to complex many arenes including benzene, naphthalene, biphenyl and pyrene. The resulting adducts form unusual supramolecular binary stacks. In addition, these adducts display unique luminescent properties which make them useful materials for organic light emitting diodes (OLED). Some of these adducts form microporous solids used for gas storage.

Neutral and Cationic Lewis acids in molecular and supramolecular chemistry.

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Selected Publications

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C. R. Wade, F. P. Gabbaï "Two-electron redox chemistry and reversible umpolung of a gold-antimony bond" Angew. Chem. Int. Ed. 2011, in press.

C. R. Wade, T.-P. Lin, R. C. Nelson, E. A. Marder, J. T. Miller, F. P. Gabbaï "Synthesis, structure and properties of a T-shaped 14-electron stiboranyl-gold complex" J. Am. Chem. Soc. 2011, 133, 8948-8955.

H. Zhao, F. P. Gabbaï "A bidentate Lewis acid with a telluronium ion as an anion-binding site" Nature Chem. 2010, 2, 984-990.

T. P. Lin, C. R. Wade, L. M. Pérez , F. P. Gabbaï "A mercury antimony interaction" Angew. Chem. Int. Ed. 2010, 49, 6357-6360.

P. Gualco, T.-P. Lin, M. Sircoglou, M. Mercy, S. Ladeira, G. Bouhadir, L. M. Pérez, A. Amgoune, L. Maron, F. P. Gabbaï, D. Bourissou "Gold->Silane and Gold->Stannane Complexes: Coordination of Saturated Molecules as sigma-Acceptor Ligands" Angew. Chem. Int. Ed. 2009,49, 9892-9895.

Y. Kim, H. Zhao, F. P. Gabbaï "Sulfonium Boranes for the Selective Complexation of Cyanide Ions in Water" Angew. Chem. Int. Ed. 2009, 49, 4957-4960.

Y. Kim, F. P. Gabbaï "Cationic boranes for the complexation of fluoride ions in water below the 4 ppm maximum contaminant level" J. Am. Chem. Soc. 2009, 131, 3363-3369.

C.-W. Chiu, Y. Kim, F. P. Gabbaï "Lewis Acidity Enhancement of Triarylboranes via Peripheral Decoration with Cationic Groups" J. Am. Chem. Soc. 2009, 131, 60-61.

T. W. Hudnall, Y. Kim, M. W. P. Bebbington, D. Bourissou, F. P. Gabbaï "Fluoride Ion Chelation By a Bidentate Phosphonium/Borane Lewis Acid" J. Am. Chem. Soc. 2008, 130, 10890-10891.

M. Kim, T. J. Taylor, F. P. Gabbaï "Hg(II)---Pd(II) Metallophilic Interactions" J. Am. Chem. Soc. 2008, 130, 6332-6333.

T. W. Hudnall, F. P. Gabbaï "Ammonium boranes for the selective complexation of cyanide or fluoride ions in water" J. Am. Chem. Soc. 2007, 129, 11978-11986.

C.-W. Chiu, F. P. Gabbaï "Structural changes accompanying the stepwise population of a B-C pi-bond" Angew. Chem. Int. Ed., 2007, 46 6878-6881.

C.-W. Chiu, F. P. Gabbaï "A 9-borylated acridinyl radical" Angew. Chem. Int. Ed. 2007, 46, 1723-1725.