Synthesis of Tröger’s base analogues
(2024) KEML10 20241Department of Chemistry
- Abstract
- This project aims to use the Tröger’s base molecule to synthesize a linearly heptakis-Tröger’s base. The furthest this project reached was the synthesis of the linearly fused tris-Tröger’s base analogue. To reach this compound, nine synthesis steps were preformed starting with an aniline analogue. The aniline was first halogenated and then condensed into the first Tröger’s base analogue. This was followed by a dehalogenation, amination, amine protection, alkylation of the benzylic position and lastly separation of two diastereomers by dry column vacuum chromatography. After this point, two more reactions are preformed including a deprotection and protection reaction before the final condensation reaction was preformed to yield the linearly... (More)
- This project aims to use the Tröger’s base molecule to synthesize a linearly heptakis-Tröger’s base. The furthest this project reached was the synthesis of the linearly fused tris-Tröger’s base analogue. To reach this compound, nine synthesis steps were preformed starting with an aniline analogue. The aniline was first halogenated and then condensed into the first Tröger’s base analogue. This was followed by a dehalogenation, amination, amine protection, alkylation of the benzylic position and lastly separation of two diastereomers by dry column vacuum chromatography. After this point, two more reactions are preformed including a deprotection and protection reaction before the final condensation reaction was preformed to yield the linearly fused tris-Tröger’s base analogue. (Less)
- Popular Abstract
- Supramolecular chemistry can be thought of as the chemistry that studies how molecules interact with each other to form large and complex structures. These large molecular structures can be made so that they have specific desired properties or shapes that can be utilized for a specific purpose, such as transporting smaller molecules around our bodies. To make a supramolecule, a good starting block is needed and one of these is the Tröger’s base molecule. This specific molecule is suitable because of its unique structure that resembles a V shape, gives rise to a cavity in which molecules that possess specific properties can be attached to. In this project the Tröger’s base molecule has been used as a starting block to make a final molecule... (More)
- Supramolecular chemistry can be thought of as the chemistry that studies how molecules interact with each other to form large and complex structures. These large molecular structures can be made so that they have specific desired properties or shapes that can be utilized for a specific purpose, such as transporting smaller molecules around our bodies. To make a supramolecule, a good starting block is needed and one of these is the Tröger’s base molecule. This specific molecule is suitable because of its unique structure that resembles a V shape, gives rise to a cavity in which molecules that possess specific properties can be attached to. In this project the Tröger’s base molecule has been used as a starting block to make a final molecule consisting of two of these molecules connected in a straight chain, a linearly fused tris-Tröger’s base analogue.
This project has followed the synthetic pathway previously developed by the Wärnmark group. The first part of this project consisted of making several modifications of the Tröger’s base molecule in such a way that the two diastereomer of Tröger’s base could be separated and so that multiple of these molecules could be connected in a straight chain. Diastereomer are two molecules that are made up of the same atoms and connected in identical ways but arranged differently in 3D-space. The second part thus consisted of connecting two of these modified molecules in a chain. (Less)
Please use this url to cite or link to this publication:
http://lup.lub.lu.se/student-papers/record/9170986
- author
- Sandberg, Martin LU
- supervisor
- organization
- course
- KEML10 20241
- year
- 2024
- type
- M2 - Bachelor Degree
- subject
- keywords
- Organic chemistry, Tröger's base, Supramolecular Chemistry, Dry column vacuum chromatography
- language
- English
- id
- 9170986
- date added to LUP
- 2024-08-12 12:34:19
- date last changed
- 2024-08-12 12:34:19
@misc{9170986,
abstract = {{This project aims to use the Tröger’s base molecule to synthesize a linearly heptakis-Tröger’s base. The furthest this project reached was the synthesis of the linearly fused tris-Tröger’s base analogue. To reach this compound, nine synthesis steps were preformed starting with an aniline analogue. The aniline was first halogenated and then condensed into the first Tröger’s base analogue. This was followed by a dehalogenation, amination, amine protection, alkylation of the benzylic position and lastly separation of two diastereomers by dry column vacuum chromatography. After this point, two more reactions are preformed including a deprotection and protection reaction before the final condensation reaction was preformed to yield the linearly fused tris-Tröger’s base analogue.}},
author = {{Sandberg, Martin}},
language = {{eng}},
note = {{Student Paper}},
title = {{Synthesis of Tröger’s base analogues}},
year = {{2024}},
}