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Framing the chalcogen-bonding interaction in the supramolecular toolbox for solid-state applications

Biot, Nicolas 2019. Framing the chalcogen-bonding interaction in the supramolecular toolbox for solid-state applications. PhD Thesis, Cardiff University.
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Out of the supramolecular toolbox, Secondary Bonding Interactions (SBIs) have been a topic of growing interest from the scientific community during the last decades, particularly halogen- and chalcogen-bonding. Those interaction are composed of orbital mixing, electrostatic and dispersion components. Heavier halogen (X) and chalcogen (E) atoms bonded to organic molecules present an anisotropic charge distribution. Specifically, a region of positive potential called a -hole can be found co-linear but opposite to the C-X or C-E bonds. Chalcogen atoms are able to form two covalent bonds and thus, exhibit two -holes. This ability allows them to be inserted in aromatic cycles making the C-E bonds less reactive compared to that of C-X. Those advantages make the chalcogen-bonding an interaction of choice to build new supramolecular architectures. However, the field still lacks a recognition motif showing fidelity and stability (chapter I). In consequence, this work presents the synthesis of a recognition motif bearing Se and Te atoms and showing a strong recognition persistence at the solid -state, namely the CGP array (chapter II). This building block can be easily substituted in 2-positions by various functional groups leading to a strengthening of the interaction or to the introduction of valuable properties. For instance, 1-pyrenyl derivatives have been synthesised showing that organic semi-conductor material can be synthesised relying on EB and − stacking interactions to organise in the solid-state (chapter II). Further functionalisation allowed us to build supramolecular polymers in the form of co-crystal showing an orthogonal behaviour of EB and XB interactions (chapter III). The CGP scaffold could also be functionalised in 5-position leading to the formation of unprecedented multi-type interactions recognition motifs (chapter IV). Exploiting the parallel use of HB and EB, we have synthesised ribbon, wire-like structures and hetero-molecular dimers.

Item Type: Thesis (PhD)
Date Type: Completion
Status: Unpublished
Schools: Chemistry
Date of First Compliant Deposit: 5 February 2020
Last Modified: 29 Mar 2021 12:53

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