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Synthesis and applications of chiral polyether macrocycles

Defense Thèse de doctorat : Univ. Genève, 2018 - Sc. 5268 - 2018/09/20
Abstract A single-step methodology was previously developed to transform unsaturated polyether macrocycles into chiral crown ethers (dr > 98:2). This tandem amidation-olefin transposition process involving aromatic amines under basic conditions was further explored and used for different applications during this PhD. First, development of a new methodology with aliphatic amines, by preformation of the bis-amides and subsequent olefin transpositions, afforded new chiral crown ethers. Then, cryptands were obtained thanks to a late-stage functionalization of some chiral crown ethers. These new receptors exhibited a heteroditopic character toward salts made of sodium and linear anions in particular, which was demonstrated by 1H NMR spectroscopy and solid state structure analysis. Finally, when chiral crown ethers are synthesized with certain fluorescent aromatic amides (pyrene, perylene, NMI or fluorene derivatives), a strong excimer fluorescence was measured due to the spatial proximity of the fluorescent arene moieties. The study of the chiroptical properties of these enantiopure macrocycles proved to be a rare examples of allied +/- ECD and on/off CPL reversible switches.
Keywords Chiral polyether macrocyclesAsymmetric PTCCryptandHeteroditopic receptorECDCPLReversible switches
URN: urn:nbn:ch:unige-1104978
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Research group Groupe Lacour
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HOMBERG, Alexandre. Synthesis and applications of chiral polyether macrocycles. Université de Genève. Thèse, 2018. doi: 10.13097/archive-ouverte/unige:110497 https://archive-ouverte.unige.ch/unige:110497

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Deposited on : 2018-11-07

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