Synthesis and properties of Novel 4,5-Diaminonaphthalimides
Synthesis and properties of Novel 4,5-Diaminonaphthalimides
This thesis presents work carried out into the synthesis and properties of novel 4,5-diaminonaphthalimides. Previous work had identified that these compounds could be synthesised through a short reaction sequence but a very limited number of examples had been produced.
With some modifications, the structure of 4,5-diaminonaphthalimides suggests a number of applications. The diamine functionality suggests the formation of complexes and if chiral amines were used asymmetric synthesis as a possibility. Naphthalimides are known to intercalate into DNA and so compounds of this nature may have interesting anti-cancer activity. Finally diaminonaphthalimides are strongly fluorescent and this in combination with the chelation potential of the diamine functionality may afford ion and molecular sensors. The first section of this thesis reviews these areas of research and demonstrates how diaminonaphthalimides might contribute to these areas.
The second section describes the synthesis of 4,5-diaminonaphthalimides and illustrates the variety of compounds that may be synthesised. In addition this section explores the applications to fluorescence sensing and asymmetric synthesis. 4,5-Diaminonaphthalimides are shown to undergo chelation enhanced quenching (HEQ) and chelation enhanced fluorescence (CHEF) with various transition metal ions. The precise features are shown to be dependent on the metal ion present. The mass spectroscopic results discussed in this section show 4,5-diaminonaphthalimides to be a new class of supramolecular compound as they show pre-assembly around alkali earth metal ions. 4,5-Diaminonaphthalmines were also used as catalysts in asymmetric reactions where they show some catalytic activity in the addition of diethylzinc to benzaldehyde.
University of Southampton
Morris, Ian Patrick
05bbf47c-d2de-459a-80b9-c1f3a1142dd0
1999
Morris, Ian Patrick
05bbf47c-d2de-459a-80b9-c1f3a1142dd0
Morris, Ian Patrick
(1999)
Synthesis and properties of Novel 4,5-Diaminonaphthalimides.
University of Southampton, Doctoral Thesis.
Record type:
Thesis
(Doctoral)
Abstract
This thesis presents work carried out into the synthesis and properties of novel 4,5-diaminonaphthalimides. Previous work had identified that these compounds could be synthesised through a short reaction sequence but a very limited number of examples had been produced.
With some modifications, the structure of 4,5-diaminonaphthalimides suggests a number of applications. The diamine functionality suggests the formation of complexes and if chiral amines were used asymmetric synthesis as a possibility. Naphthalimides are known to intercalate into DNA and so compounds of this nature may have interesting anti-cancer activity. Finally diaminonaphthalimides are strongly fluorescent and this in combination with the chelation potential of the diamine functionality may afford ion and molecular sensors. The first section of this thesis reviews these areas of research and demonstrates how diaminonaphthalimides might contribute to these areas.
The second section describes the synthesis of 4,5-diaminonaphthalimides and illustrates the variety of compounds that may be synthesised. In addition this section explores the applications to fluorescence sensing and asymmetric synthesis. 4,5-Diaminonaphthalimides are shown to undergo chelation enhanced quenching (HEQ) and chelation enhanced fluorescence (CHEF) with various transition metal ions. The precise features are shown to be dependent on the metal ion present. The mass spectroscopic results discussed in this section show 4,5-diaminonaphthalimides to be a new class of supramolecular compound as they show pre-assembly around alkali earth metal ions. 4,5-Diaminonaphthalmines were also used as catalysts in asymmetric reactions where they show some catalytic activity in the addition of diethylzinc to benzaldehyde.
This record has no associated files available for download.
More information
Published date: 1999
Identifiers
Local EPrints ID: 463742
URI: http://eprints.soton.ac.uk/id/eprint/463742
PURE UUID: 808df976-7b59-4d44-9856-870cee615084
Catalogue record
Date deposited: 04 Jul 2022 20:56
Last modified: 23 Jul 2022 02:15
Export record
Contributors
Author:
Ian Patrick Morris
Download statistics
Downloads from ePrints over the past year. Other digital versions may also be available to download e.g. from the publisher's website.
View more statistics