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Synthèse organique de macrocycles conjugués par réaction de Perkin

Abstract : The controlled organic synthesis of carbon nanobelts has been scientific challenge for a long time. Such cylindrical polycyclic aromatic compounds can be defined as sections of carbon nanotubes that are larger than wide. Interesting electronic properties could result from the curvature of their pi system.These last years, our team has developed a general synthetic approach for the formation of carboxy-functionalised polycyclic aromatic compounds. This approach involves the Perkin reaction of arylacetic acids with arylglyoxylic acids, in order to form conjugated and flexible elongated precursors. The last step is an intramolecular cyclisation, or “graphitisation”, which rigidifies the precursor and yields a fully conjugated final molecule. Applying this approach, our team has synthesised several new linear polycyclic aromatic compounds.The aim of this thesis is to adapt the Perkin reaction for the formation of aromatic nanobelts. A first challenge has been solved by synthesising and fully characterising several flexible and conjugated macrocycles. Some of those macrocyclic compounds have been obtained with unexpectedly good yields using a high dilution addition technique. Graphitisations have been tried on some of those macrocycles by different synthetic methods, i.e. photochemistry and palladium catalysis, but none of them led to the formation of the desired aromatic nanobelt. However, by modifying the initial structure of some of the building blocks, we obtained more flexible conjugated macrocycles, which then reacted, by photocyclisation, to form conjugated and non-planar rigid macrocycles with atypical structures.
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https://tel.archives-ouvertes.fr/tel-02021955
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Submitted on : Sunday, February 17, 2019 - 1:01:13 AM
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  • HAL Id : tel-02021955, version 1

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Antoine Robert. Synthèse organique de macrocycles conjugués par réaction de Perkin. Chimie organique. Université de Bordeaux, 2017. Français. ⟨NNT : 2017BORD0935⟩. ⟨tel-02021955⟩

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