Abstract
This work describes the synthesis and studies of sulfur containing π
conjugated heterocycles, which are considered interesting motifs in the field
of molecular electronics.
The first project, which is covered in Chapter 1, concerns the
functionalization of tetracycle dibenzo[bc,fg][1,4]dithiapentalene (DDP).
Attempts to prepare the S-O analog are also discussed.
Chapter 2, focuses upon the studies performed on DDP and other sulfur
containing π conjugated organic molecules. Organic Field Effect Transistor
devices were fabricated and their performances were evaluated.
Chapter 3 entails the synthesis of dimeric structures of redox active
system tetrathiafulvalene (TTF). Molecules with different conjugation
pathways bridging two TTFs were synthesized and studied using CV and
DPV in order to probe the electronic interaction between these two redox
units.
The last aspect of this thesis, which is presented in Chapter 4, deals with
the incorporation of two TTF units into acetylenic scaffolds to generate
greater redox active cyclic systems. Improvements of a previously reported
macrocycle synthesis and development of asymmetric macrocyclic systems
incorporating two TTF moieties were achieved. The instability issue of
synthetic intermediates bearing free acetylenes was overcome employing a
new strategy. This involved the end–capping of the acetylenic functionality
with triphenylphosphine gold motif producing stable organometallic
complexes, which could be subsequently used in Sonogashira cross coupling
reactions to construct such macrocycles.
conjugated heterocycles, which are considered interesting motifs in the field
of molecular electronics.
The first project, which is covered in Chapter 1, concerns the
functionalization of tetracycle dibenzo[bc,fg][1,4]dithiapentalene (DDP).
Attempts to prepare the S-O analog are also discussed.
Chapter 2, focuses upon the studies performed on DDP and other sulfur
containing π conjugated organic molecules. Organic Field Effect Transistor
devices were fabricated and their performances were evaluated.
Chapter 3 entails the synthesis of dimeric structures of redox active
system tetrathiafulvalene (TTF). Molecules with different conjugation
pathways bridging two TTFs were synthesized and studied using CV and
DPV in order to probe the electronic interaction between these two redox
units.
The last aspect of this thesis, which is presented in Chapter 4, deals with
the incorporation of two TTF units into acetylenic scaffolds to generate
greater redox active cyclic systems. Improvements of a previously reported
macrocycle synthesis and development of asymmetric macrocyclic systems
incorporating two TTF moieties were achieved. The instability issue of
synthetic intermediates bearing free acetylenes was overcome employing a
new strategy. This involved the end–capping of the acetylenic functionality
with triphenylphosphine gold motif producing stable organometallic
complexes, which could be subsequently used in Sonogashira cross coupling
reactions to construct such macrocycles.
| Original language | English |
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| Publisher | Department of Chemistry, Faculty of Science, University of Copenhagen |
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| Publication status | Published - 2014 |