Abstract
This thesis describes the synthesis, reactivity and investigated optical- and redox properties of an array of polycyclic aromatic hydrocarbons (PAHs) used as -systems for extended dithiafulvene (DFF) or tetrathiafulvalene (TTF) systems. TTF is a well-known redox-active molecule with promising electronic properties for applications in supramolecular chemistry and organic conducting materials. The PAHs presented in this thesis each focuses on a different property specifically prominent in their structure.
The thesis starts with Chapter 1 by introducing various concepts within organic chemistry and briefly covers the development and story of TTF and its current role in the field of organic semiconductors.
Chapter 2 focuses on the 9,9-bifluorenylidene systems and the strain around its exocyclic double bond. Three different extended TTF systems containing the same PAH core has been synthesized with varying degrees of flexibility, which has significant influence on the properties of each system.
Chapter 3 explores the DTF motif extended with a 7-membered ring and how a distorted system consisting of larger rings affect the redox properties of the DTF.
Chapter 4 describes the synthesis of a series of donor and acceptor systems separated in the middle by a tetrahedral carbon atom, and the possibility of electronic communication between the units via spiroconjugation has been studied. Furthermore, the systems experience conformational changes, which are observed on NMR spectroscopic timescale.
Chapter 5 investigates functionalization of small PAH systems with a focus on pyrene in an attempt to create a generalized protocol for use in larger PAH systems. Numerous different reaction conditions are carried out, however only with limited success.
The thesis starts with Chapter 1 by introducing various concepts within organic chemistry and briefly covers the development and story of TTF and its current role in the field of organic semiconductors.
Chapter 2 focuses on the 9,9-bifluorenylidene systems and the strain around its exocyclic double bond. Three different extended TTF systems containing the same PAH core has been synthesized with varying degrees of flexibility, which has significant influence on the properties of each system.
Chapter 3 explores the DTF motif extended with a 7-membered ring and how a distorted system consisting of larger rings affect the redox properties of the DTF.
Chapter 4 describes the synthesis of a series of donor and acceptor systems separated in the middle by a tetrahedral carbon atom, and the possibility of electronic communication between the units via spiroconjugation has been studied. Furthermore, the systems experience conformational changes, which are observed on NMR spectroscopic timescale.
Chapter 5 investigates functionalization of small PAH systems with a focus on pyrene in an attempt to create a generalized protocol for use in larger PAH systems. Numerous different reaction conditions are carried out, however only with limited success.
| Originalsprog | Engelsk |
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| Forlag | Department of Chemistry, Faculty of Science, University of Copenhagen |
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| Antal sider | 237 |
| Status | Udgivet - 2024 |