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Study Of The Preparation And Photo-Activity Of The Substituted Diphenylamine And Diphenylether Cyclopentadienyliron Complexes

Posted on:2011-12-03Degree:MasterType:Thesis
Country:ChinaCandidate:G C ZhangFull Text:PDF
GTID:2121360305484966Subject:Organic Chemistry
Abstract/Summary:PDF Full Text Request
In order to study the reactivity of the chlorobenzene cyclopentadienyliron complex in the aromatic nucleophilic substitution reaction (SNAr) and the effect of the substituent on nucleophilic reagent, the SNAr of several aniline derivatives and phenol derivatives with the chlorobenzene cyclopentadienyliron complex was investigated. The results showed that the substituted groups on the phenol and aniline greatly affected the SNAr reaction and the electron-withdrawing group on aniline and the electron-donating group on phenol made the SNAr easier.Several asymmetric diphenylamine and diphenylether cyclopentadienyliron complexes were synthesized via the SNAr, including 4-chloro-3-nitrodiphenylamine cyclopentadienyliron complex, 4-bromodiphenylamine cyclopentadienyliron complex, 2,4,6-tribromo diphenylamine cyclopentadienyliron complex,4-nitrodiphenylamine cyclopentadienyliron complex,2-nitrodiphenylamine cyclopentadienyliron complex, diphenylether cyclopentadienyliron complex, 4-methoxyldiphenylether cyclopentadienyliron complex, 4-chlorodiphenylether cyclopentadienyliron complex, 4-chloro-3-methyldiphenylether cyclopentadienyliron complex, 3-methyldiphenylether cyclopentadienyliron complex,2-ethoxyldiphenylether cyclopentadienyliron complex,3-methoxyldiphenylether cyclopentadienyliron complex. Except diphenylether cyclopentadienyliron complex, all the compounds were not reported before. The structure of the complexes were identified by IR, LC-MC and 1HNMR.The UV-Vis absorption of the complexes were studied. The absorption above 300nm caused by d-d transition of the complexes make them suitable with the halogen lamp which is usually used in the visible light-curing. From the fluorescence spectra and emission spectra of the complexes, the results showed that all the complexes possess fluorenscence emission, and the fluorescence intensity of the substituted diphenylether cyclopentadienyliron complexes were stronger than that of the substituted diphenylamine cyclopentadienyliron complexes. Using the complexes synthesized as photoinitiators, epoxide E-44 as oligomer, the efficiencies of the complexes in the cationic polymerizations were evaluated by NIR spectroscopy.
Keywords/Search Tags:nucleophilic aromatic substitution reaction (S_NAr), cyclopentadienyliron complex, cationicphotopolymerization, UV-Vis absorption, fluorescence spectra, photoinitiating activity
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