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Study on the Synthesis and Molecular Recognition of Aromatic Ring Supramolecular Compounds

Author: ShenWeiLi
Tutor: ShuangShaoMin
School: Shanxi University
Course: Analytical Chemistry
Keywords: CTV derivatives Point Fan - E Synthesis Molecular recognition Molecular spectroscopy
CLC: O621.2
Type: Master's thesis
Year: 2009
Downloads: 51
Quote: 0
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Abstract


The first chapter CTV compounds and hole Fan compounds belong to the same aromatic ring class supramolecular compounds through hydrogen bonding, hydrophobic, pi-pi and inclusion role and neutral molecules to form inclusion complexes are an important class of supramolecular host compounds. This chapter provides a brief overview of the CTV compound and the structural characteristics of the hole Fan compounds, described in detail the methods for their synthesis, molecular recognition feature and Research. The second chapter of vanillin as a raw material, respectively, with dimethyl sulfate, diethyl sulfate, and n-propyl bromide reaction, the resulting product is then reduced with sodium borohydride to resveratrol, and finally with 2 the trimerization condensation reaction method , 3,7,8,12,13 - hexamethoxyflavone -10,15 - dihydro - three benzene ring nonane (CTV), the 2,7,12 - triethoxyethane -3,8,13 - Trimethoxybenzaldehyde based -10,15 - dihydro - benzene ring nonane (including ethoxylated CTV), 2,7,12 - Sanbing--3,8,13 - trimethoxy -10,15 - dihydro - three benzene ring nonane (containing propoxy CTV) the three CTV Compounds, respectively, three CTV classes compound with anhydrous aluminum trichloride demethylation reaction generates 2,7,12 - trihydroxy -3 8,13 - trimethoxyphenyl -10,15 - dihydro - 3 benzene ring nonane (hydroxyl group-containing CTV), and compare them to a yield of 78%, 55%, 10%, respectively, the results show that with the CTV raw materials demethylation to generate the highest yield of hydroxyl-containing CTV. The structures of the compounds were characterized by nuclear magnetic resonance and infrared spectroscopy, and the effects of UV and fluorescence spectral characteristics of these compounds in organic solvents of different polarity. The third chapter vanillin as a raw material, dried over anhydrous ethanol as solvent and 1,3 - dibromopropane the reaction of 1,3 - bis (4 of - formyloxy -2 - methoxy-phenyl) propane, and then sodium borohydride, the reduction reaction is generated 1,3 - dibromopropane by the reaction of 1,3 - bis (4 - (hydroxymethyl) -2 - methoxyphenyl) propane, and finally, condensation in highly dilute acidic catalytic conditions with secondary trimerization synthesis cave Fan-E product isolated and purified by silica gel column using NMR structure of the characterization, and the effects of various organic solvents, UV and fluorescence characteristics were screened out for the hole Fan-E small molecular recognition of ethyl acetate, dioxane, acetonitrile solvent has good solubility in these solvents hole Fan-E spectral signal. Chapter UV fluorescence spectrometry research in ethyl acetate, dioxane, acetonitrile solvent points Fan-E the neutral molecular CH 2 the Cl 2 , CHCl 3 interaction. The results show that: Fan-E in the hole with a solvent of chloroform strong ability to identify, the formation of a 1:1 host-guest inclusion inclusion, double reciprocal curve and non-linear fitting method to calculate inclusion constants. In ethyl acetate hole Fan-E the best effect of inclusion of the chloroform, followed by dioxane and acetonitrile, instructions the solvent hole Fan-E inclusion ability to have a certain impact. Computer simulation of molecular mechanics and space matching principle further confirmed that the cave Fan-E and chloroform to form a stable host-guest inclusion complexes. The study also found that the hole Fan-E and the role of the methylene chloride is weak, non-linear fitting method to calculate the resulting binding constants show that the hole Fan-E and methylene chloride the weak packet cooperation with, may be due to methylene chloride the volume is relatively small in size does not match with the the points fan-E cavity.

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