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Synthesis of Tröger's Base Analogues

Arbós Labal, Neus LU (2023) KEMP30 20222
Department of Chemistry
Abstract
Tröger’s Base analogues have been widely used as scaffolds in supramolecular systems due to their structure, rigidity, and chirality. This project aims to synthesize two diastereomer Tröger’s Base analogues that could be used as building blocks for a linearly fused heptakis-Tröger’s Base. Initially, two haloaniline moieties were condensed into a halogenated Tröger’s Base analogue, which was then functionalized with amino groups in the aromatic rings and menthyl side chains at the benzylic positions of the diazocine bridge. The addition of new controlled stereogenic centres in the benzylic positions generated two diastereomers, which were separated using chromatography and will provide two possible routes for the synthesis of heptakis-TB.
Popular Abstract
Popular Science Summary: A brick for molecular buildings

This project is in the field of supramolecular chemistry, which was summarized by Nobel Prize winner Jean Marie Lehn as “chemistry beyond the molecule”. Supramolecular chemistry goes beyond the study of single molecules and reactions and focuses on how different molecules interact and arrange themselves in bigger and intricate systems without changing their individual structure.

A relevant molecule used in supramolecular chemistry is Tröger’s Base. This molecule is rigid, with a fixed and well-known shape that makes it useful as a building block in structures with a controlled geometry. The goal of this project is to synthesize an analogue of Tröger’s Base that could later be... (More)
Popular Science Summary: A brick for molecular buildings

This project is in the field of supramolecular chemistry, which was summarized by Nobel Prize winner Jean Marie Lehn as “chemistry beyond the molecule”. Supramolecular chemistry goes beyond the study of single molecules and reactions and focuses on how different molecules interact and arrange themselves in bigger and intricate systems without changing their individual structure.

A relevant molecule used in supramolecular chemistry is Tröger’s Base. This molecule is rigid, with a fixed and well-known shape that makes it useful as a building block in structures with a controlled geometry. The goal of this project is to synthesize an analogue of Tröger’s Base that could later be condensed to form a 7-membered chain with a C-like shape.

Since the goal structure would be C-shaped, other molecules could be stored in the empty space in the middle, for example drugs. Therefore, this structure could serve as a cavity where the drugs would be protected, so they could travel through the body safely. In addition, the building blocks that could be condensed to create the C-shaped cavity have also been designed so that cells would recognize the structure, allowing for the drugs to be delivered.

The focus of this project has been the synthesis of the building blocks for the cavity: starting from a very simple molecule, new parts have been added until the goal structure was obtained. The process can be viewed as if one was building a lego, using chemical reactions to stick the pieces together until the desired shape is obtained. Since the final structure needs to be a very specific one, these parts need to be added very carefully and one by one, making sure the result of each step is the expected one.

After 6 synthesis steps from the starting material, the desired building blocks were obtained, allowing for further investigation towards the building of the final C-shaped product in the future. (Less)
Please use this url to cite or link to this publication:
author
Arbós Labal, Neus LU
supervisor
organization
course
KEMP30 20222
year
type
L3 - Miscellaneous, Projetcs etc.
subject
keywords
Organic synthesis, supramolecular chemistry, Tröger's Base, heptakis-Tröger's Base
language
English
id
9111521
date added to LUP
2023-03-02 10:53:57
date last changed
2023-03-02 10:53:57
@misc{9111521,
  abstract     = {{Tröger’s Base analogues have been widely used as scaffolds in supramolecular systems due to their structure, rigidity, and chirality. This project aims to synthesize two diastereomer Tröger’s Base analogues that could be used as building blocks for a linearly fused heptakis-Tröger’s Base. Initially, two haloaniline moieties were condensed into a halogenated Tröger’s Base analogue, which was then functionalized with amino groups in the aromatic rings and menthyl side chains at the benzylic positions of the diazocine bridge. The addition of new controlled stereogenic centres in the benzylic positions generated two diastereomers, which were separated using chromatography and will provide two possible routes for the synthesis of heptakis-TB.}},
  author       = {{Arbós Labal, Neus}},
  language     = {{eng}},
  note         = {{Student Paper}},
  title        = {{Synthesis of Tröger's Base Analogues}},
  year         = {{2023}},
}