Design and development of electro-responsive [8]annulene switches
Author
Summary, in English
This thesis describes studies regarding the design, synthesis, and analysis of new types of electro-responsive [8]annulene-based switches.
A starting material for the targeted material is dibenzo[a,e]cyclooctatetraene (dbCOT). The first part of the thesis describes an improved synthesis of this structure using a copper(I) catalyzed decarboxylative approach. Using this method, dbCOT was prepared in three steps from commercially available compounds, with a good overall yield of 62%. In addition, the same method is applied to the synthesis of two related diareno[a,e]cyclooctatetraenes.
In the second part, the design, retrosynthetic analysis, and synthesis of pseudo-conjugated 5,12-alkyne linked dbCOT oligomers with two, three, and five dbCOT units, are discussed. The synthesis of dbCOT oligomers was accomplished in five to nine steps from dbCOT and commercially available dibenzosuberenone. The properties of these structures with respect to reversible topological switching are then investigated using chemical and electrochemical methods. The structures were found to efficiently accommodate stable and reversible switching over many cycles.
A starting material for the targeted material is dibenzo[a,e]cyclooctatetraene (dbCOT). The first part of the thesis describes an improved synthesis of this structure using a copper(I) catalyzed decarboxylative approach. Using this method, dbCOT was prepared in three steps from commercially available compounds, with a good overall yield of 62%. In addition, the same method is applied to the synthesis of two related diareno[a,e]cyclooctatetraenes.
In the second part, the design, retrosynthetic analysis, and synthesis of pseudo-conjugated 5,12-alkyne linked dbCOT oligomers with two, three, and five dbCOT units, are discussed. The synthesis of dbCOT oligomers was accomplished in five to nine steps from dbCOT and commercially available dibenzosuberenone. The properties of these structures with respect to reversible topological switching are then investigated using chemical and electrochemical methods. The structures were found to efficiently accommodate stable and reversible switching over many cycles.
Department/s
Publishing year
2022-05-02
Language
English
Full text
Document type
Dissertation
Publisher
Lund University, Faculty of Science, Department of Chemistry, Centre for Analysis and Synthesis
Topic
- Chemical Sciences
Keywords
- electro-responsive switches
- molecular switches
- [8]annulenes
- dibenzo[a,e]cyclooctatetraene
Status
Published
Supervisor
ISBN/ISSN/Other
- ISBN: 978-91-7422-875-5
- ISBN: 978-91-7422-874-8
Defence date
30 May 2022
Defence time
09:00
Defence place
Kemicentrum, KC:A, Lunds universitet. Join via zoom: https://lu-se.zoom.us/j/69795304516
Opponent
- Mogens Brøndsted Nielsen (Professor)