Quaternary ammonium salts as chiral ionic liquids and as antimicrobial surfaces.
Item
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Title
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Quaternary ammonium salts as chiral ionic liquids and as antimicrobial surfaces.
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Identifier
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AAI3284414
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identifier
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3284414
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Creator
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Thomas, Marie F.
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Contributor
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Adviser: Robert R. Engel
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Date
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2007
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Language
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English
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Publisher
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City University of New York.
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Subject
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Chemistry, Organic
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Abstract
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The focus of this research has been the preparation and characterization of a variety of new monocationic and polycationic ammonium organic salts that can be used as ionic liquids and as agents that can be used to generate antimicrobial surfaces.;Ionic liquids are anhydrous salts that have melting points below 100°C and are usually liquid at room temperature. These materials have little vapor pressure at standard temperature and pressure, are non-flammable, and are thermally stable. The focus is on the synthesis of chiral ionic liquids. Such liquids may give selectivity in asymmetric synthesis, chiral separations and electrochemical processes. The ionic liquids that have been developed are based on the racemic and chiral forms of 3-chloro-1, 2-propane diol. Development work has been done with the racemic alkyl halide and these efforts have been extended to the more expensive chiral species. A series of racemic and chiral ionic liquids have been successfully synthesized. These materials may be useful catalysts and/or solvents for organic reactions which exhibit enhanced reaction rates and/or selectivity in polar solvents.;In addition to making chiral ionic liquids, we have taken advantage of the antimicrobial property of quaternary ammonium salts and developed different methods for applying them to surfaces (porous and non-porous) rendering them antimicrobial. The cationic lipophilic salts used in this study were based on DABCO (diazabicyclo [2.2.2] octane). Carbohydrate-based polycationic salts were developed that can gel water and alcohols. The resulting gels exhibited significant biological activity against the Gram (+) bacterium S. aureus. Mannose functionalized PAMAM dendrimers and polyester fabrics were successfully modified with the DABCO salts. These materials have been shown to exhibit antibacterial activity against Gram (+) and Gram (-) bacteria. Patents are pending for some of these procedures.
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Type
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dissertation
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Source
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PQT Legacy CUNY.xlsx
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degree
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Ph.D.
