Thesis

Investigation into the use of phenyl azides for the photoimmobilisation of DNA

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Awarding institution
  • University of Strathclyde
Date of award
  • 2010
Thesis identifier
  • T12598
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Abstract
  • This thesis details the research into the use of phenyl azides for the photoimmobilisation of DNA, with particular focus on characterising their photochemistry and the design of a library of novel phenyl azides for the functionalisation of a variety of substrates. Three phenyl azides containing a para carboxylic acid have been prepared with their photochemical activation rates characterised. Upon illumination at 365 nm with and without the presence of a primary amine first order rate kinetic were observed. As a result from an investigation into further modification of the three synthesised phenyl azides, 2-(4-azidophenyl)acetic acid [3] was selected for the core structure for future applications. The photochemistry of the chosen phenyl azide was verified by 1H NMR, by illumination at 365 nm in the presence of a primary amine. The photoimmobilisation of DNA was successfully achieved on quartz, epoxide polymer and gold via the functionalisation with the chosen phenyl azide 2-(4- azidophenyl)acetic acid [3]. Characteristic fluorescence and surface enhanced resonance Raman spectroscopy (SERRS) spectra observed of the dye labelled DNA upon the quartz substrate and resonance Raman spectroscopy (RRS) and SERRS StreamLine™ maps prepared depicting the site of photoimmobilisations on the epoxide polymer and gold substrate respectively. Two novel photoactive dip-pen nanolithography (DPN) inks were also prepared containing the chosen phenyl azide 2-(4-azidophenyl)acetic acid [3] with diffusion coefficients obtained. The diffusion coefficient for the thioctic acid based ink for the gold substrate was 10 times larger than that of the silane based ink for the silicon dioxide substrate. The novel inks were prepared with the intention to photoimmobilise DNA in a similar manner to that previously described.
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DOI
Date Created
  • 2010
Former identifier
  • 814432

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