Triphenylene as a Scaffold for New Molecular Materials
type: CreativeWork
description: The work described in this thesis centres around our desire to use triphenylene as the scaffold for building new molecular materials. This has been approached in three different ways; firstly a twin linked by pyrrole units, secondly by twinning with triazoles, and finally via the formylation of triphenylene. A tetra-hexyloxysubstituted dipyrrolyltriphenylene twin had previously been synthesised in the group, however characterisation was difficult and therefore a twin with improved solubility was designed. The synthesis of tetra-decyloxysubstituted dipyrrolyltriphenylene was completed successfully, but the twinning of the compound could not be achieved. One possible explanation was interference of the long alkyl chains in the neighbouring positions to the pyrrole units. A new target precursor was designed with just two alkyl chains on the triphenylene. Previous work in the group had shown difficulties in the synthesis of the di-hexyloxysubstituted triphenylene, however with careful manipulations the synthesis was successful. New complications were found with the solubility of the di-hexyloxysubstituted dipyrrolyltriphenylene that could not be overcome. At this point crystals of the tetra-hexyloxysubstituted dipyrrolyltriphenylene twin had been obtained and full characterisation achieved. With the explosion of Click chemistry in the recent years, a twin linked by triazoles was targeted. The twin was designed from a tetra-hexyloxysubstituted diazidetriphenylene, coupled with di-hexyloxysubstituted diacetylenetriphenylene. The diacetylene triphenylene was synthesised successfully following on from the work achieved in the first project. Two routes were explored for the synthesis of the diazide. The first, a direct conversion of the dibromide to the diazide, gave no reaction. The second route was a series of manipulations starting from the dinitrotriphenylene. Some difficulties were found with the reduction of the dinitro compound to the diamine, however these were overc…
abstract: The work described in this thesis centres around our desire to use triphenylene as the scaffold for building new molecular materials. This has been approached in three different ways; firstly a twin linked by pyrrole units, secondly by twinning with triazoles, and finally via the formylation of triphenylene. A tetra-hexyloxysubstituted dipyrrolyltriphenylene twin had previously been synthesised in the group, however characterisation was difficult and therefore a twin with improved solubility was designed. The synthesis of tetra-decyloxysubstituted dipyrrolyltriphenylene was completed successfully, but the twinning of the compound could not be achieved. One possible explanation was interference of the long alkyl chains in the neighbouring positions to the pyrrole units. A new target precursor was designed with just two alkyl chains on the triphenylene. Previous work in the group had shown difficulties in the synthesis of the di-hexyloxysubstituted triphenylene, however with careful manipulations the synthesis was successful. New complications were found with the solubility of the di-hexyloxysubstituted dipyrrolyltriphenylene that could not be overcome. At this point crystals of the tetra-hexyloxysubstituted dipyrrolyltriphenylene twin had been obtained and full characterisation achieved. With the explosion of Click chemistry in the recent years, a twin linked by triazoles was targeted. The twin was designed from a tetra-hexyloxysubstituted diazidetriphenylene, coupled with di-hexyloxysubstituted diacetylenetriphenylene. The diacetylene triphenylene was synthesised successfully following on from the work achieved in the first project. Two routes were explored for the synthesis of the diazide. The first, a direct conversion of the dibromide to the diazide, gave no reaction. The second route was a series of manipulations starting from the dinitrotriphenylene. Some difficulties were found with the reduction of the dinitro compound to the diamine, however these were overc…
author: Turner, Rebecca
language: en
date published: 2015-06
date modified: 2026-07-24T02:12:08Z
provider: University of East Anglia
publisher: Networked Digital Library of Theses and Dissertations
type: WebPage
source organization: University of East Anglia