Novel Materials for optical storage
Tutor / director / evaluatorHvilsted, Soren
Document typeMaster thesis (pre-Bologna period)
Rights accessRestricted access - confidentiality agreement
A divergent approach to synthesise dendritic aliphatic polyester structure based on 2,2- bis(hydroxymethyl) propionic acid (bis-MPA) which at second generation is tried to attach on its surface 6[4’-(4-cyanophenyl-azo)phenoxy) hexanoic acid to make it a useful material for inscribing holograms, is described. The synthesis developed begins with the compound, 2-methyl-2-phenyl-5-(8- bromooctyl)-m-dioxane, which was prepared in order to obtain 2-(8-azidooctyl) propane- 1,3-diol, which constituted the core of the macromolecule. Dendritic growth occurred by the use of the anhydride of isopropylidene-2,2- bis(hidroxymethyl) propionic acid, which was previously synthesised through selfdehydration, using N,N dicyclohexylcarbodimide (DCC) as a reagent. This acetonide protected groups are easy removed using an ion exchange resin (DOWEX 50W- X2) in methanol as it was done. So repeating the explained procedure different generations of the dendritic structure could be obtained. Once the second generation was obtained, the azobenzene derivative, mentioned previously, was attached to the surface of the dendritic structure but no pure product was obtained. After this reaction not all the dendron reacted and remaining acid was also detected. Furthermore, other compounds appeared due to secondary reactions. Due to the complexity of separating the different compounds in the final product it was concluded that other strategies must be followed in order to attach azobenzene functionality and obtain a pure product. To sum up, the whole process requires seven synthetic and three chromatographic steps to develop the second generation dendron with peripheral azobenzene moieties and azide functionality in the focal point, but last stage of the proposed synthesis does not work.
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