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Thermodynamically controlled synthesis of covalent nanocapsules
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Title
Thermodynamically controlled synthesis of covalent nanocapsules
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Liu
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Xuejun
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Xuejun Liu
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Advisory Committee
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Ralf Warmuth
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Romsted
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Laurence
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Laurence Romsted
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Seidel
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Daniel
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Daniel Seidel
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Piotrowiak
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Advisory Committee
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Piotr Piotrowiak
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Rutgers University
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Graduate School - New Brunswick
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theses
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2008
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2008-10
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English
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electronic
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xxiii, 215 pages
Abstract
Chapter 1 gives a general overview about molecular container compounds.
In Chapter 2, a new method for the room temperature stabilization of fluorophenoxycarbene is described. In this approach, photolysis of incarcerated fluorophenoxydiazirine generated fluorophenoxycarbene in the inner phase of a hemicarcerand, which protected the carbene from dimerization. As a result of its high stability, 1H, 13C and 19F NMR spectroscopic properties of this carbene were obtained at room temperature. The reaction of the incarcerated carbene with bulk phase water and its inner phase conformation were explored.
The synthesis of covalent nanocapsules is challenging and current multi-step syntheses give nanocapsules only in relatively low overall yield. In Chapter 3 and 4, a dynamic covalent chemistry approach has been developed to prepare nanocapsules in high yield in a single step from multiple small building blocks. Nanometersized molecular capsules of this type have potential for applications in drug, pesticide and RNA delivery and as nanoreactors. In Chapter 3, three different nanocapsules, whose structures resemble a distorted tetrahedron, octahedron, or square antiprism, are described. These capsules are prepared by condensation reactions between 4, 6, and 8 tetraformyl cavitands 40 and 8, 12, and 16 ethylenediamines 43, respectively. They have cavity volumes of 450-3000 Å3. In Chapter 4, synthesis of a series of distorted tetrahedral nanocapsules through reaction of 40 with rigid linear diamines 48a-c is described. These capsules form 1:1 and 1:2 complexes with tetraalkylammonium salts of appropriate size, in which the tetraalkylammonium guests are encapsulated in the cavity of the nanocapsule.
In Chapter 5, dynamic combinatorial libraries (DCL) of polyimino nanocapsules are constructed by reacting 40 with a combination of 2 or 3 different diamine linkers 41, 44d, 48a, and 48b.
In Chapter 6, the syntheses of water-soluble nanocapsules are described. They are prepared by attaching hydrophilic functional groups and charged groups to the nanocapsules. Binding studies in water revealed that these nanocapsules encapsulate negatively charged organic compounds. The water soluble nanocapsules possess large portals and a roomy inner cavity and potentially may serve as devices for drug delivery and controlled release applications.
In Chapter 2, a new method for the room temperature stabilization of fluorophenoxycarbene is described. In this approach, photolysis of incarcerated fluorophenoxydiazirine generated fluorophenoxycarbene in the inner phase of a hemicarcerand, which protected the carbene from dimerization. As a result of its high stability, 1H, 13C and 19F NMR spectroscopic properties of this carbene were obtained at room temperature. The reaction of the incarcerated carbene with bulk phase water and its inner phase conformation were explored.
The synthesis of covalent nanocapsules is challenging and current multi-step syntheses give nanocapsules only in relatively low overall yield. In Chapter 3 and 4, a dynamic covalent chemistry approach has been developed to prepare nanocapsules in high yield in a single step from multiple small building blocks. Nanometersized molecular capsules of this type have potential for applications in drug, pesticide and RNA delivery and as nanoreactors. In Chapter 3, three different nanocapsules, whose structures resemble a distorted tetrahedron, octahedron, or square antiprism, are described. These capsules are prepared by condensation reactions between 4, 6, and 8 tetraformyl cavitands 40 and 8, 12, and 16 ethylenediamines 43, respectively. They have cavity volumes of 450-3000 Å3. In Chapter 4, synthesis of a series of distorted tetrahedral nanocapsules through reaction of 40 with rigid linear diamines 48a-c is described. These capsules form 1:1 and 1:2 complexes with tetraalkylammonium salts of appropriate size, in which the tetraalkylammonium guests are encapsulated in the cavity of the nanocapsule.
In Chapter 5, dynamic combinatorial libraries (DCL) of polyimino nanocapsules are constructed by reacting 40 with a combination of 2 or 3 different diamine linkers 41, 44d, 48a, and 48b.
In Chapter 6, the syntheses of water-soluble nanocapsules are described. They are prepared by attaching hydrophilic functional groups and charged groups to the nanocapsules. Binding studies in water revealed that these nanocapsules encapsulate negatively charged organic compounds. The water soluble nanocapsules possess large portals and a roomy inner cavity and potentially may serve as devices for drug delivery and controlled release applications.
Note
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Ph.D.
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Includes bibliographical references.
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Chemistry and Chemical Biology
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Nanostructured materials
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Microencapsulation
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Graduate School - New Brunswick Electronic Theses and Dissertations
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ETD doctoral
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Xuejun Liu
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Rutgers University. Graduate School - New Brunswick
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