St Andrews Research Repository

St Andrews University Home
View Item 
  •   St Andrews Research Repository
  • Chemistry (School of)
  • Chemistry
  • Chemistry Theses
  • View Item
  •   St Andrews Research Repository
  • Chemistry (School of)
  • Chemistry
  • Chemistry Theses
  • View Item
  •   St Andrews Research Repository
  • Chemistry (School of)
  • Chemistry
  • Chemistry Theses
  • View Item
  • Login
JavaScript is disabled for your browser. Some features of this site may not work without it.

Novel derivatives of DPP and related heterocycles

Thumbnail
View/Open
ColinMortonPhDThesis.pdf (31.62Mb)
Date
1999
Author
Morton, Colin J. H.
Supervisor
Smith, D. M.
Metadata
Show full item record
Altmetrics Handle Statistics
Abstract
This thesis discusses the synthesis of new organic, heterocyclic materials for potential application as pigments. Chapter 1 comprises an introduction to the field of pigment and dye chemistry, discussing the rudimentary elements of colour theory, before advancing to a review of the pertinent literature regarding high performance organic pigments. In particular, the development of 1,4-diketopyrrolo[3,4-c]pyrrole (DPP) pigments is described and the central objective of synthesising alkenyl-DPPs is outlined. Chapters 2 and 3 describe synthetic efforts towards alkenyl-DPPs, employing retro Diels-Alder methodology. The reactions involving the furan-acrylonitrile adduct as the nitrile component in the standard DPP synthesis led mainly to aromatisation of the bicyclic system and the cyclopentadiene-acrylonitrile adduct failed to react altogether. The explanation for this failure has been investigated. In the course of this these studies, several DPPs incorporating a secondary alkyl substituent were prepared, not least a novel cyclohexenyl-DPP. Chapter 4 describes the use of α β-unsaturated nitriles in the standard DPP synthesis. These behaved as Michael acceptors and in the case of cinnamonitriles led to a new family of coloured materials, namely substituted 4-hydroxy-2/7- cyclopenta[c]pyrrol-1-one-5-carbonitriles. Chapter 5 describes the corresponding reaction of cinnamate esters, but in these cases bicyclic systems were not formed. The reactions are analogous to Claisen acylations and the stereochemistry of the products varied according to the substituents. Chapter 6 contains the detailed experimental work for these investigations and concludes with a portfolio of X-ray structural data.
Type
Thesis, PhD Doctor of Philosophy
Collections
  • Chemistry Theses
URI
http://hdl.handle.net/10023/15291

Items in the St Andrews Research Repository are protected by copyright, with all rights reserved, unless otherwise indicated.

Advanced Search

Browse

All of RepositoryCommunities & CollectionsBy Issue DateNamesTitlesSubjectsClassificationTypeFunderThis CollectionBy Issue DateNamesTitlesSubjectsClassificationTypeFunder

My Account

Login

Open Access

To find out how you can benefit from open access to research, see our library web pages and Open Access blog. For open access help contact: openaccess@st-andrews.ac.uk.

Accessibility

Read our Accessibility statement.

How to submit research papers

The full text of research papers can be submitted to the repository via Pure, the University's research information system. For help see our guide: How to deposit in Pure.

Electronic thesis deposit

Help with deposit.

Repository help

For repository help contact: Digital-Repository@st-andrews.ac.uk.

Give Feedback

Cookie policy

This site may use cookies. Please see Terms and Conditions.

Usage statistics

COUNTER-compliant statistics on downloads from the repository are available from the IRUS-UK Service. Contact us for information.

© University of St Andrews Library

University of St Andrews is a charity registered in Scotland, No SC013532.

  • Facebook
  • Twitter