UNIGE document Doctoral Thesis
previous document  unige:110497  next document
add to browser collection
Title

Synthesis and applications of chiral polyether macrocycles

Author
Director
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
Identifiers
URN: urn:nbn:ch:unige-1104978
Full text
Thesis (13.4 MB) - document accessible for UNIGE members only Limited access to UNIGE (until 2020-11-05)
Structures
Research group Groupe Lacour
Citation
(ISO format)
HOMBERG, Alexandre. Synthesis and applications of chiral polyether macrocycles. Université de Genève. Thèse, 2018. https://archive-ouverte.unige.ch/unige:110497

37 hits

0 download

Update

Deposited on : 2018-11-07

Export document
Format :
Citation style :