Synthesis of Linear Fused Tröger’s Base Analogues
(2021) KEMP30 20202Department of Chemistry
- Abstract
- Tröger’s base molecule has a unique V-shaped cavity and a chiral structure. These molecules can be fused together in a linear fashion to create either tubular structure or zigzag structure. Different fields can be benefited from the applications of these molecules.
Previous studies carried out in the Wärnmark group led to 30-step synthesis route to get a linearly fused heptakis-Tröger’s Base analogue. The aim of this project was to reply the synthetic route and to improve it where possible. Through a nine-step reaction route, a linear fused tris-Tröger’s base analogue has been synthesized, collecting valuable material for further synthesis of the Tröger’s Base (TB) analogue and the characterizations of the TB intermediates.
The... (More) - Tröger’s base molecule has a unique V-shaped cavity and a chiral structure. These molecules can be fused together in a linear fashion to create either tubular structure or zigzag structure. Different fields can be benefited from the applications of these molecules.
Previous studies carried out in the Wärnmark group led to 30-step synthesis route to get a linearly fused heptakis-Tröger’s Base analogue. The aim of this project was to reply the synthetic route and to improve it where possible. Through a nine-step reaction route, a linear fused tris-Tröger’s base analogue has been synthesized, collecting valuable material for further synthesis of the Tröger’s Base (TB) analogue and the characterizations of the TB intermediates.
The synthesis started from two aniline derivatives, which modified and condensed led to a Tröger’s Base analogue. In the end, two diastereomers were formed and separated through column chromatography, and followed by a deprotection of the amine groups of one of them. The whole covered synthesis included different steps and reactions, like condensations (as mentioned), amine protection with TMS groups, Pd-catalysed reactions, aminations, and electrophilic aromatic substitution. After this project, a large amount of products are available and the studies for the improvement of all the steps possible can be continued. (Less) - Popular Abstract
- Supramolecular chemistry, or as it is known as chemistry beyond the molecule, can be described as the field that studies interactions, weak and non-covalent, between two or more molecules. When we think about this type of interactions, we often think about two components that are bound to each other: the smallest one “substrate” is the one bound to the biggest one “receptor”.
One of the valuable structural motifs for supramolecular applications is the Tröger’s Base (TB), a molecule that has a rigid, V-shaped structure with two aromatic rings that are forming a hydrophobic and concave cavity in the molecule, usually used as a building block for compounds that end working as ligands.
The main work during this project has been... (More) - Supramolecular chemistry, or as it is known as chemistry beyond the molecule, can be described as the field that studies interactions, weak and non-covalent, between two or more molecules. When we think about this type of interactions, we often think about two components that are bound to each other: the smallest one “substrate” is the one bound to the biggest one “receptor”.
One of the valuable structural motifs for supramolecular applications is the Tröger’s Base (TB), a molecule that has a rigid, V-shaped structure with two aromatic rings that are forming a hydrophobic and concave cavity in the molecule, usually used as a building block for compounds that end working as ligands.
The main work during this project has been following and replying the already written (on previous studies in the Wärnmark group) synthetic route, to be able to get the linearly fused heptakis-Tröger’s Base analogue. Also, an important part of this work has been trying to improve some steps of the synthesis, when possible and characterize the intermediates. Due to the period we were able to work in the lab, only nine of the 30-steps of the reaction route have been done, but a linear fused Tris-Tröger’s base analogue has been synthesized.
The whole covered synthesis included different steps and reactions, like condensations (as mentioned), amine protection with TMS groups, Pd-catalysed reactions, aminations, and electrophilic aromatic substitution. (Less)
Please use this url to cite or link to this publication:
http://lup.lub.lu.se/student-papers/record/9041303
- author
- Ramon, Julia LU
- supervisor
- organization
- course
- KEMP30 20202
- year
- 2021
- type
- L3 - Miscellaneous, Projetcs etc.
- subject
- keywords
- Tröger's Base, organic chemistry, synthesis
- language
- English
- id
- 9041303
- date added to LUP
- 2021-03-29 14:44:46
- date last changed
- 2021-03-29 14:44:46
@misc{9041303,
abstract = {{Tröger’s base molecule has a unique V-shaped cavity and a chiral structure. These molecules can be fused together in a linear fashion to create either tubular structure or zigzag structure. Different fields can be benefited from the applications of these molecules.
Previous studies carried out in the Wärnmark group led to 30-step synthesis route to get a linearly fused heptakis-Tröger’s Base analogue. The aim of this project was to reply the synthetic route and to improve it where possible. Through a nine-step reaction route, a linear fused tris-Tröger’s base analogue has been synthesized, collecting valuable material for further synthesis of the Tröger’s Base (TB) analogue and the characterizations of the TB intermediates.
The synthesis started from two aniline derivatives, which modified and condensed led to a Tröger’s Base analogue. In the end, two diastereomers were formed and separated through column chromatography, and followed by a deprotection of the amine groups of one of them. The whole covered synthesis included different steps and reactions, like condensations (as mentioned), amine protection with TMS groups, Pd-catalysed reactions, aminations, and electrophilic aromatic substitution. After this project, a large amount of products are available and the studies for the improvement of all the steps possible can be continued.}},
author = {{Ramon, Julia}},
language = {{eng}},
note = {{Student Paper}},
title = {{Synthesis of Linear Fused Tröger’s Base Analogues}},
year = {{2021}},
}