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Synthesis and characterization of novel ferrocene ester Central Fan

Author: GaoBo
Tutor: YangBingQin
School: Northwestern University
Course: Organic Chemistry
Keywords: Supramolecular ester ferrocenophanes synthesis characterization crystal structure
CLC: O627.81
Type: Master's thesis
Year: 2009
Downloads: 131
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Abstract


Supramolecular chemistry as an important domain has been developed rapidly in recent years.Supramolecular chemistry,which represents the next level of complexity of the material following elementary particles,nuclei,atoms and molecules,is the chemistry beyond molecules.Supramolecular species are represented by its components,the building space with super-structure,and the nature of non-covalent among bonds among inter-moleculars which putting components together.Supramolecular which is formed through inter-molecular recognition and self-assembly is closely related to life science, materials science and information science,and also has great development prospects.Molecular recognition is one of the core research domain of supramoledular chemistry.The so-called molecular recognition is the process of selective binding between the main(or receptor) and the object(or substrate).Cyclophanes is a kind of orbicular compounds which can be the host in supramoledular chemistry,and it is divided into macrocycle and circlet.The trait of circlet cyclophanes are theirπ-electrons delocalizing among rings,so there is much dissimilarity of physics and chemistry between circlet cyclophanes benzene rings.In these ferrocenophanes,many of the important properties of the parent ferrocene are retained,such as high electron density,aromaticity,thermal stability,favourable reaction activity and reversible redox characteristics.These ferrocenophanes are expected to show unique chemical properties owing to the functionality of the sidearm.Not only ferrocenophanes which combine ferrocene having aromaticity with cyclic structure have thermodynamic stability and chemical stability,but also many of the important properties of the parent ferrocene are retained.So it can enhance the application performance of bridging structure,and the wide range of applications can be shown.There are many reports about the use of ferrocenophanes,such as the basic materials of the new types of steady opto-electronics materials,the procursors of special polymer through ROP reaction,as well as the simulation of biological enzymes.This dissertation reviewed the status、significance、development、research status of cyclophanes in supramolecular chemistry.Through analysis of the structural characteristics and application prospect of many ferrocenophanes,we designed five novel circlet ferrocenophanes.Through a series of reactions,we obtained 1,1’-diacetylferrocene, 1,1 ’-ferrocene dicarboxylic,1,1’-Ferrocene-di(carbonylchloride).Then by esterification of 1,1’-ferrocene-di(carbonyl chloride) with kinds of dihydroxy-ethyl aniline under a high dilute condition,we synthesized:1,9-dicarbonyl-2,8-dioxo-5-phenyl -N-[9]ester ferrocenophane a,1,9-dicarbonyl-2,8-dioxo-5-(4-fluoro)phenyl-N-[9]ester ferrocenophane b,1,9-dicarbonyl-2,8-dioxo-5-(4-methyl)phenyl-N-[9]ester ferr -ocenophane c,1,9-dicar-bonyl-2,8-dioxo-5-(4-methoxy)phenyl-N-[9]ester ferrocenoph -ane d,1,9-dicarbonyl-2,8-dioxo-5-(4-nitro)phenyl-N-[9]ester ferrocenophane e.And the ester ferrocenophanes were characterized by UV,~1H NMR,IR,elemental analysis and MS.We analyzed their syntheses conditions and molecture structures.Suitable crystals of ester ferrocenophane a and b were obtained,and their crystal structures were determined by X-ray single crystal diffraction.

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CLC: > Mathematical sciences and chemical > Chemistry > Organic Chemistry > Elements in organic compounds > Ⅷ of group elements, organic compounds > Iron organic compounds
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