The Synthesis of Model Asphaltenes

  • Barnaby Haire

Student thesis: Phd


Derivatives of polyaromatic core structures representing 'island' and 'archipelago' structural types were synthesised, functionalised and characterised for use in developing a fundamental understanding of asphaltene aggregation and deposition. Tetraphenylcyclopentadiene derivatives were subjected to Diels-Alder cycloaddition enabling a suite of tetra- and hexaphenylbenzenes. Subsequent oxidative aromatic coupling provided a key synthetic step in the formation of functionalised tribenzopentaphene and hexabenzocoronene derivatives. The reaction procedure for isolation of 1-nitroperylene was refined and enabled the installation of thiophene, carbazole and pyridine functionalities, with alkyl functionality incorporated by Sonogashira coupling and acylation to permit solution-based analysis. Nucleophilic aromatic substitution and nucleophilic substitution chemistries were performed deliver a series of alkyl-tethered pyrene and phenanthrene derivatives. Preliminary investigations performed by academic partners into model compounds deposition behaviour utilising atomic force microscopy and adsorption isotherms have provided information regarding substrate affinity through surface coverage and morphology analysis.
Date of Award1 Aug 2018
Original languageEnglish
Awarding Institution
  • The University of Manchester
SupervisorPeter Quayle (Supervisor) & Stephen Yeates (Supervisor)


  • Heteroaromatic
  • Petroleum
  • Synthesis
  • Asphaltene
  • Polyaromatic

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