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Design and development of electro-responsive [8]annulene switches

Tasic, Magdalena LU (2022)
Abstract
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... (More)
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. (Less)
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author
supervisor
opponent
  • Professor Brøndsted Nielsen, Mogens, Köpenhamns universitet
organization
publishing date
type
Thesis
publication status
published
subject
keywords
electro-responsive switches, molecular switches, [8]annulenes, dibenzo[a,e]cyclooctatetraene
pages
143 pages
publisher
Lund University, Faculty of Science, Department of Chemistry, Centre for Analysis and Synthesis
defense location
Kemicentrum, KC:A, Lunds universitet. Join via zoom: https://lu-se.zoom.us/j/69795304516
defense date
2022-05-30 09:00:00
ISBN
978-91-7422-875-5
978-91-7422-874-8
language
English
LU publication?
yes
id
79f14871-6457-4aa5-86d4-8578d2bc441d
date added to LUP
2022-05-02 09:09:23
date last changed
2022-05-04 08:13:29
@phdthesis{79f14871-6457-4aa5-86d4-8578d2bc441d,
  abstract     = {{This thesis describes studies regarding the design, synthesis, and analysis of new types of electro-responsive [8]annulene-based switches.<br/>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.<br/>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.}},
  author       = {{Tasic, Magdalena}},
  isbn         = {{978-91-7422-875-5}},
  keywords     = {{electro-responsive switches; molecular switches; [8]annulenes; dibenzo[a,e]cyclooctatetraene}},
  language     = {{eng}},
  month        = {{05}},
  publisher    = {{Lund University, Faculty of Science, Department of Chemistry, Centre for Analysis and Synthesis}},
  school       = {{Lund University}},
  title        = {{Design and development of electro-responsive [8]annulene switches}},
  url          = {{https://lup.lub.lu.se/search/files/117483373/Magdalena_Tasic_OPEN.pdf}},
  year         = {{2022}},
}