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The synthesis and study of fluorescent dendritic molecules

El-Betany, Alaa 2010. The synthesis and study of fluorescent dendritic molecules. PhD Thesis, Cardiff University.

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The research described in this thesis had the aim of preparing and investigating a new series of polyamidoamine (PAMAM) dendrons with a fluorescent core for use in biological applications (e.g. labelling and imaging). Potential fluorophore cores based on N-alkylamino, N-arylamino or imidazole naphthalimide derivatives were screened and derivatives of 7H-benz[de]benzimidazo[2,1-a]isoquinoline-7-one were selected. Using this core several new water soluble fluorescent PAMAM dendrons were prepared and their photochemical and physicochemical properties studied. The dendrons are all fluorescent due to the core but in some cases this is modulated by interactions with the amine units in the dendritic structure. For all dendrons the fluorescence is linearly correlated with concentration and the pH of the aqueous solvent has a significant effect for both UV absorbance (ground state) and fluorescent emission (excited state). The strongest fluorescent emission of all carboxylate-terminated dendrons was pH 6. Physiochemical studies indicate that the self-diffusion coefficient and hydrodynamic radii are unaffected by concentration suggesting that there is no aggregation.  The confirmed properties (i.e. water solubility, high fluorescence at near neutral pH, and no aggregation) indicate that these new dendrons are promising for applications in biological studies. For example, initial studies suggest that the permeability of fluorescent core PAMAM dendrons across cell monolayers appear to be a function of the size of the dendrons. Preliminary studies also show that the fluorescent core binds to DNA, presumably by interaction of the aromatic core.

Item Type: Thesis (PhD)
Status: Unpublished
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Date of First Compliant Deposit: 30 March 2016
Last Modified: 14 Oct 2019 13:43

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