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Functionalized chiral macrocycles and molecular cages

Joanna Szymkowiak

Abstract

Synthesis of chiral macrocyles and covalent organic cages with well-defined structure and programmable properties is one of the leading tasks in contemporary supramolecular organic chemistry. Cyclocondensation reactions between chiral dipodal amines and di- or tripodal aldehydes, developed in Organic Stereochemistry Group, provide quantitatively molecular macrocycles and polyimine cages. The change of the nature of aromatic and/or amine linker significantly affects properties of the given product like its solubility, packing in the crystal and hence porosity and sorption properties of the bulk material. Introduction of o-hydroxyl groups in the aromatic ring of an aldehyde increases chemical stability of the imine bond. Moreover, the number and position of hydroxyl groups in the aromatic linker and reaction conditions affect stoichiometry of the products. In this work, the issues related to the synthesis and structural studies of functional chiral polyhydroxylated macrocycles and molecular cages are discussed in details.
Record ID
UAMf6985773e1964d6ab1a857644d4bbf91
Diploma type
Doctor of Philosophy
Author
Title in Polish
Funkcjonalizowane chiralne makrocykle i klatki molekularne
Title in English
Functionalized chiral macrocycles and molecular cages
Language
pol (pl) Polish
Certifying Unit
Wydział Chemii [nowa struktura organizacyjna] (SNŚ/WC)
Scientific discipline (2.0)
6.5 chemical sciences
Status
Finished
Year of creation
2018
Defense Date
30-11-2018
Title date
30-11-2018
Supervisor
URL
https://hdl.handle.net/10593/24146 Opening in a new tab
Keywords in English
chiral macrocycles, molecular cages, upramolecular architectures, circular dichroism spectroscopy
Abstract in English
Synthesis of chiral macrocyles and covalent organic cages with well-defined structure and programmable properties is one of the leading tasks in contemporary supramolecular organic chemistry. Cyclocondensation reactions between chiral dipodal amines and di- or tripodal aldehydes, developed in Organic Stereochemistry Group, provide quantitatively molecular macrocycles and polyimine cages. The change of the nature of aromatic and/or amine linker significantly affects properties of the given product like its solubility, packing in the crystal and hence porosity and sorption properties of the bulk material. Introduction of o-hydroxyl groups in the aromatic ring of an aldehyde increases chemical stability of the imine bond. Moreover, the number and position of hydroxyl groups in the aromatic linker and reaction conditions affect stoichiometry of the products. In this work, the issues related to the synthesis and structural studies of functional chiral polyhydroxylated macrocycles and molecular cages are discussed in details.
Thesis file
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Uniform Resource Identifier
https://researchportal.amu.edu.pl/info/phd/UAMf6985773e1964d6ab1a857644d4bbf91/
URN
urn:amu-prod:UAMf6985773e1964d6ab1a857644d4bbf91

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