Expansion of a family of phenanthridinium-based heterocyclic derivatives

Eadie, Roslyn (2011) Expansion of a family of phenanthridinium-based heterocyclic derivatives. PhD thesis, University of Glasgow.

Abstract

This thesis focuses on the expansion of a family of phenanthridine derivatives; 5-(2-aminoethyl)-phenanthridinium chlorides (AEPs), 2,3-dihydro-1H-imidazo[1,2-f]phenanthridiniums (DIPs) and 1,2,3,12b-tetrahydroimidazo[1,2-f]phenanthridines (TIPs), and their possible applications.
AEPs and DIPs with extended alkyl chains were synthesised and investigated for indications of possible surfactant-like behaviour through the use of 1H NMR spectroscopy. Correlations between the shift in the water signal and the concentrations of the AEPs with an alkyl chain length of 11, 12 and 14 carbons in deutero-chloroform showed positive results for micelle formation. Preliminary studies of their use in inorganic-organic molecular systems as tube growth components were also performed.
Incorporation of two crown ether moieties, 4-aminobenzo-18-crown-6 and trans-di(aminobenzo)-18-crown-6, into the frameworks was achieved. Complexation of potassium in the crown attachment of the TIP monomer was observed via 1H NMR and fluorescence spectroscopy.
Structurally diverse primary aryl amines were used as reactants to gain further insight into their effect on the product isolated as a result of the steric and electronic effects from aryl substituents, neighbouring hydroxyls and pyridine nitrogen atoms. UV-vis and 1H NMR spectroscopy enabled analysis and reaction monitoring which revealed that excessively electron withdrawing groups and sterically hindered amines do not allow for isolation of the common TIP structure but enter into one of two pathways for the formation of the DIP and AEP structures.
Finally, a range of TIPs and DIPs were synthesised which incorporate different functionalities, providing a platform for further derivitisation or use.

• Item Type: Thesis (PhD)
• Qualification Level: Doctoral
• Keywords: Heterocycles, Phenanthridinium, Derivatives
• Subjects: Q Science > QD Chemistry
• Colleges/Schools: College of Science and Engineering > School of Chemistry
• Supervisor's Name: Cronin, Professor Leroy
• Date of Award: 2011
• Embargo Date: 19 March 2022
• Depositing User: Miss Roslyn Eadie
• Unique ID: glathesis:2011-3292
• Copyright: Copyright of this thesis is held by the author.
• Date Deposited: 30 Mar 2012
• Last Modified: 19 Mar 2021 08:28
• Thesis DOI: 10.5525/gla.thesis.3292
• URI: https://theses.gla.ac.uk/id/eprint/3292