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Supramolecular porphyrin arrays on DNA and SWNT scaffolds

Supramolecular porphyrin arrays on DNA and SWNT scaffolds
Supramolecular porphyrin arrays on DNA and SWNT scaffolds
A variety of supramolecular porphyrin arrays on DNA or single walled carbon nanotube scaffolds are presented herein. A novel porphyrin modified nucleoside with multiple degrees of freedom about the linking moiety has been synthesised. Oligonucleotide strands containing the novel ‘flexible’ porphyrin modified nucleoside or a previously published ‘rigid’ linked porphyrin modified nucleoside were synthesised. The resulting systems were analysed by photospectrometric techniques. Stable B form duplexes were observed in all cases, with the porphyrin modifications imparting a stabilising effect on the duplexes, the degree of stabilisation the novel porphryin monomer provides is of a similar level to that of the rigid linked monomer. Excitonic coupling of the porphyrins is observed; the different monomers incorporated into DNA show different effects in the circular dichroism spectra, which may be explained through the increased conformational freedom of the ‘flexible’ linker. The synthesis of a novel anthraquinone modified nucleoside is presented. Modified DNA strands containing both porphyrin modifications and anthraquinone modifications were synthesised and analysed electrochemically. Cyclic voltammetry has shown that the inclusion of multiple porphyrin modifications increase the electron transfer rate to the anthraquinone redox marker. The synthesese of a novel ferrocenyl modified nucleotide, a novel naphthalene diimide modified nucleotide and an alternative synthesis route for a ruthenium tris-bipyridyl nucleoside are presented. Homo- and hetero-porphyrin single walled carbon nanotube adducts have been prepared with neutral, tetra-anionic and tetra-cationic porphyrins. Significantly elevated loading levels have been observed for the mixed charge species which forms a 1:1 salt on the nanotube surfaces
Brewer, Ashley
d10b9ab3-b920-498b-8a3c-b4b5d16106e5
Brewer, Ashley
d10b9ab3-b920-498b-8a3c-b4b5d16106e5
Stulz, Eugen
9a6c04cf-32ca-442b-9281-bbf3d23c622d

Brewer, Ashley (2011) Supramolecular porphyrin arrays on DNA and SWNT scaffolds. University of Southampton, Chemistry, Doctoral Thesis, 269pp.

Record type: Thesis (Doctoral)

Abstract

A variety of supramolecular porphyrin arrays on DNA or single walled carbon nanotube scaffolds are presented herein. A novel porphyrin modified nucleoside with multiple degrees of freedom about the linking moiety has been synthesised. Oligonucleotide strands containing the novel ‘flexible’ porphyrin modified nucleoside or a previously published ‘rigid’ linked porphyrin modified nucleoside were synthesised. The resulting systems were analysed by photospectrometric techniques. Stable B form duplexes were observed in all cases, with the porphyrin modifications imparting a stabilising effect on the duplexes, the degree of stabilisation the novel porphryin monomer provides is of a similar level to that of the rigid linked monomer. Excitonic coupling of the porphyrins is observed; the different monomers incorporated into DNA show different effects in the circular dichroism spectra, which may be explained through the increased conformational freedom of the ‘flexible’ linker. The synthesis of a novel anthraquinone modified nucleoside is presented. Modified DNA strands containing both porphyrin modifications and anthraquinone modifications were synthesised and analysed electrochemically. Cyclic voltammetry has shown that the inclusion of multiple porphyrin modifications increase the electron transfer rate to the anthraquinone redox marker. The synthesese of a novel ferrocenyl modified nucleotide, a novel naphthalene diimide modified nucleotide and an alternative synthesis route for a ruthenium tris-bipyridyl nucleoside are presented. Homo- and hetero-porphyrin single walled carbon nanotube adducts have been prepared with neutral, tetra-anionic and tetra-cationic porphyrins. Significantly elevated loading levels have been observed for the mixed charge species which forms a 1:1 salt on the nanotube surfaces

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Published date: 30 April 2011
Organisations: University of Southampton, Chemistry

Identifiers

Local EPrints ID: 202885
URI: https://eprints.soton.ac.uk/id/eprint/202885
PURE UUID: ad065634-cb73-4cc8-be3a-8b351806946f
ORCID for Eugen Stulz: ORCID iD orcid.org/0000-0002-5302-2276

Catalogue record

Date deposited: 10 Nov 2011 10:12
Last modified: 06 Jun 2018 12:40

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