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

Sammanfattning: 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.