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New Directions in the Chemistry of Azo-compounds

Rasheed, Omer Khayyam

[Thesis]. Manchester, UK: The University of Manchester; 2011.

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Abstract

The synthesis and chemical reactivity of azo-dyes is reviewed and their application to the field of molecular sensors is outlined. The main body of the thesis is concerned with the development of synthetic strategies for the construction of sensing agents which are of potential value in the diagnosis of metal-dependent neurodegenerative diseases. The functionalisation of readily available azo-dyes is described including the use of Heck, Stille reactions and the application of a novel benzannulation reaction to the synthesis of benzo-fused azo-dyes. During these investigations an unprecedented redox-cyclisation reaction of naphthol-derived azo dyes was discovered, leading to the synthesis of the previously unknown 2,3-dihydro-1H-naphtho[1,2-e][1,3,4]oxadiazine ring system. These novel heterocycles were fully characterised by spectroscopic and X-ray diffraction techniques. The development of an Ullmann-type displacement reaction of halo substituted azo-dyes is also reported. This process will enable the conjugation of azo-dyes to macrocyclic systems and provides a modular approach to the synthesis of macrocycles capable of sensing heavy metals in biological systems.

Bibliographic metadata

Type of resource:
Content type:
Form of thesis:
Type of submission:
Degree type:
Master of Philosophy
Degree programme:
MPhil Chemistry
Publication date:
Location:
Manchester, UK
Total pages:
186
Abstract:
The synthesis and chemical reactivity of azo-dyes is reviewed and their application to the field of molecular sensors is outlined. The main body of the thesis is concerned with the development of synthetic strategies for the construction of sensing agents which are of potential value in the diagnosis of metal-dependent neurodegenerative diseases. The functionalisation of readily available azo-dyes is described including the use of Heck, Stille reactions and the application of a novel benzannulation reaction to the synthesis of benzo-fused azo-dyes. During these investigations an unprecedented redox-cyclisation reaction of naphthol-derived azo dyes was discovered, leading to the synthesis of the previously unknown 2,3-dihydro-1H-naphtho[1,2-e][1,3,4]oxadiazine ring system. These novel heterocycles were fully characterised by spectroscopic and X-ray diffraction techniques. The development of an Ullmann-type displacement reaction of halo substituted azo-dyes is also reported. This process will enable the conjugation of azo-dyes to macrocyclic systems and provides a modular approach to the synthesis of macrocycles capable of sensing heavy metals in biological systems.
Thesis main supervisor(s):
Language:
en

Institutional metadata

University researcher(s):

Record metadata

Manchester eScholar ID:
uk-ac-man-scw:129192
Created by:
Rasheed, Omer
Created:
18th August, 2011, 17:44:32
Last modified by:
Rasheed, Omer
Last modified:
2nd November, 2011, 15:19:35

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