Thesis

Development of new oligofluorene-functionalised truxen analogues

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Awarding institution
  • University of Strathclyde
Date of award
  • 2013
Thesis identifier
  • T13556
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Abstract
  • Interest in conjugated materials continues to increase as various types of new electronic devices based on organic semiconductors have been developed, some of which are now found in the marketplace. Many of these materials are either small molecules or polymers, both of which have their own advantages and drawbacks. Oligomers are macromolecules which can be envisioned as midway between small molecules and polymers, containing the advantages of both. In addition, while polymers are limited to one dimensional conjugated chains, oligomers have to potential to contain conjugated chains spanning over 2 dimensions, which makes their development of keen interest to those conducting research in the field of organic semiconductors. Chapter 1 details the development of organic semiconducting materials and explores their applications in devices, as well as discussing the development of star-shaped oligomers, and in particular those based around the truxene moiety. Chapters 2, 3 and 4 then present new oligofluorene-functionalised truxene analogues. Chapter 2 discusses the synthesis and optical and electrochemical properties of perfluorenehexylthiophene end capped oligofluorene-functionalised truxenes. The impotance of the position of the perfluorohexyl chain on the thiophene was investigated by the synthesis of structural isomers and comparing the optical and electrochemical properties, demonstrating that the sterics effects of the chain alter the degree of planarity within the molecules. In Chapter 3, attempts to synthesise oligofluorenes substituted with triethylene glycol (TEG) chains are discussed, as well as the synthesis of T1POLAR, an analogue of the parent T1 molecule where the fluorene moieties are substituted with TEG chains. The optical and electrochemical properties of T1POLAR are also presented. Attempts to introduce primary alkylamines at the terminal position of oligofluorene functionalised truxenes are then presented in Chapter 4. Contained within chapter 5 are the procedures for synthesis of compounds presented in chapters 2, 3 and 4.
Resource Type
DOI
Date Created
  • 2013
Former identifier
  • 1001257

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