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Novel triazine cyclophane Synthesis and Application of its intermediates

Author: LvGuoHua
Tutor: HuaChengWen
School: Northwestern University
Course: Organic Chemistry
Keywords: Supramolecular Chemistry Triazine cyclophane Crystal structure Biological testing Molecular Recognition
CLC: O626
Type: Master's thesis
Year: 2010
Downloads: 88
Quote: 0
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Abstract


In recent years the macrocyclic chemistry in the field of supramolecular chemistry has developed rapidly, the design, synthesis and applications of organic compounds with molecular recognition ability supramolecular chemistry and organic chemistry research hot spots. Cyclophane as host - guest chemistry field is very representative of the main compound has made remarkable achievements in many fields. In this thesis, the synthesis of novel aza-cyclophane target, three major new class of cyclophane compounds synthesized under relatively mild conditions through the use of cyanuric chloride and some other simple compounds. Text is divided into five parts, the main contents and conclusions are as follows: The first part is a brief introduction of host compounds in supramolecular chemistry crown ether cyclodextrin, calixarene, cyclophane CUCURBITURIL porphyrin and phthalocyanine cyclic peptide such as the basic concepts and their progress. A more detailed description of the cyclophane five Synthesis its applied research. Second part cyanuric chloride, p-nitrophenol, phenol, sodium methoxide, 4,4 '- diamino diphenyl methane and triethylamine synthesized monocyclic cyclophane 1-5a ,1-5b ,2-3a ,2-3b ,2-4 ,2-5a ,2-5b. The results show that: the synthetic cyclophane 1-5a and 1-5b, a nitro group reduction of the critical steps;, secondary acid generator in the synthesis of 2-3a ,2-3b ,2-4 ,2-5a ,2-5b The choice is very important. In addition, all ring-forming steps are required in the highly diluted otherwise obtained is a chain polymer. The third part of cyanuric chloride, 4,4 '- diaminodiphenylmethane, o-phenylenediamine, and 1,6' - hexamethylene diamine for the synthesis of bicyclic cyclophane 3-3 and 3-5. Flight mass spectrometry showed that the desired product peak, proved indeed synthesize the compound, but due bicyclic cyclophane very insoluble and its separation and purification can not lead to the elemental analysis and theoretical values ??larger difference. How can we improve the bicyclic cyclophane solubility is a follow-up to the important and difficult work. The fourth part in view of the previously synthesized cyclophane solubility than the poor characteristics, the focus of this section is to improve the solubility of cyclophane, the introduction of reactive groups to cyclophane successfully synthesized soluble cyclophane 4-3 4-5,4-6,4-7. Crystal growth hydrothermal method they obtained crystals of 4-3 and 4-6, and their structures were characterized by X-ray single crystal diffraction. Fifth part cyclophane intermediate three bacteria Bacillus subtilis, Staphylococcus aureus, Escherichia coli, and other biological testing laboratories was made for bioassay intermediates were sterilized or inhibitory effect, its effect the number of the chlorine atoms contained in the molecule, with the reduction in the number of the chlorine atom in the molecule, its bactericidal or bacteriostatic effect are also gradually becomes weak; also synthesized soluble cyclophane 4-3 and 4 - 6 recognition experiment, the UV absorption spectrum of the metal cation shows a different group of the metal ions can be identified, only some of the ions of the transition metals.

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CLC: > Mathematical sciences and chemical > Chemistry > Organic Chemistry > Heterocyclic compounds
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