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Design and Synthesis of Calixarene Molecules Containing Functional Group

Author: XieDeXun
Tutor: AnDeLie
School: Hunan University
Course: Organic Chemistry
Keywords: Calixarene Self-Assembled Monolayers(SAMs) nanocluster Sonogashira reaction
CLC: O621.25
Type: Master's thesis
Year: 2009
Downloads: 146
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Abstract


Calixarene molecule possesses a unique framework. While carrying out chemical modification in the location of its upper rim, lower rim, methylene, benzene ring skeleton and so on,We can obtain derivatives with specific functions. The applications of calixarene involve life sciences, catalysis, analytical separation, ion carriers, environmental chemistry and so on. Sulfur compounds, especially sulfhydryl(-SH) compounds have a strong coordination ability, it can form monomolecular film in the surface of many precious metals. Therefore, these substances enjoy high favor among the chemical workers and material workers in the self-assembled monolayer (Self-Assembled Monolayers, SAMs) research. This laboratory has previously designed and synthesized multi-functional sulfur aryl methyl sulfide acetylene molecule with diverse shape andπconjugated system. It is of significant importance to get some functional molecules with good assemble effect, especially those that can control cluster patterns and cluster scales.The purpose of the thesis is to design and synthesize some new calixarene derivatives of different sizes and distinguished functions; to observe its unique performance in the assembled and disassembled cluster and the control of the size and scale systematically, looking forward to discovering certain peculiar qualities and functions. RS? base has a medium coordination capacity, its sulfhydryl-bit can be broken if it is added some strong assemblies cluster. In addition, different molecules attached to the surface of metals may play different parts in the approcahing way of particles and the gathered numbers, so as to regulate the assembly effect of the nanoclusters and scale. The study is carried out not only to enrich the content of synthetic chemistry, but also have an important theoretical and practical significance in micro-self-assembly of molecular devices, as well as efficient catalysts for the creation of metal clusters.We discuss the different designs and synthesises of the two new series of calixarene derivatives from Chapter II to Chapter III. Through the protection and control of blocking group, Sonogashira coupling reaction, coupling methylthio -containing functional groups of the terminal block calixarene molecules with two precursor coupling elements, the target compounds were synthesized. Some intermediate compounds and the structures of target molecules were confirmed through 1H NMR, 13C NMR and MS. Some chemical compounds are undergoing performance testing in New York State University, hoped to form self-assembled monolayer and apply in areas such as molecular recognition in biological and molecular identification of the sensor electrode; the multi-functional group of Calixarene Derivatives are also looked forward to the new applications of the assembly of nano-cluster studies.

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CLC: > Mathematical sciences and chemical > Chemistry > Organic Chemistry > Organic Chemistry general issues > Properties of organic compounds > Chemical properties of organic reactions
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