Synthesis of Linearly Fused Tröger’s Base Analogues
(2018) KEMR31 20181Department of Chemistry
- Abstract
- The Tröger’s base molecule has a unique V-shaped cavity and can be fused together in a linear fashion to create either tubular structures or zigzag structures. These structures could be applicable in for example catalysis. The Tröger’s base scaffold is easily functionalised with different side-groups and therefore has a wide range of applications.
Previous research in the Wärnmark group had led to a thirteen-step synthesis from 4-bromo-3-methylaniline to a linearly fused heptakis-TB analogue with methoxy side-groups. The aim of this project was to repeat this synthetic route and to improve it where possible. Also, characterisations of the synthesised compounds have been provided.
This research covers the first nine steps of the... (More) - The Tröger’s base molecule has a unique V-shaped cavity and can be fused together in a linear fashion to create either tubular structures or zigzag structures. These structures could be applicable in for example catalysis. The Tröger’s base scaffold is easily functionalised with different side-groups and therefore has a wide range of applications.
Previous research in the Wärnmark group had led to a thirteen-step synthesis from 4-bromo-3-methylaniline to a linearly fused heptakis-TB analogue with methoxy side-groups. The aim of this project was to repeat this synthetic route and to improve it where possible. Also, characterisations of the synthesised compounds have been provided.
This research covers the first nine steps of the synthesis and includes a wide range of reactions, such as electrophilic aromatic substitutions, condensations, a Buchwald-Hartwig amination, a TMS and TFAA protection, and formation and separation of diastereomers. (Less) - Popular Abstract
- Supramolecular chemistry can be described as the field that studies weak, non-covalent, interactions between molecules. We often think of a bigger ‘host’ molecule that allows easy reversible coordination of smaller molecules it interacts with.
A molecule that has been envisioned for such supramolecular chemistry is Tröger’s base, which has a unique V-shaped structure and if several of these V-shaped molecules are connected together, we can think of applications such as catalysis. A catalyst is a molecule that helps the reaction to proceed faster by, for example stabilising their intermediates or bringing the molecular components closer together. Such catalysis, where different molecules end up in the V-shaped cavities and therefore get... (More) - Supramolecular chemistry can be described as the field that studies weak, non-covalent, interactions between molecules. We often think of a bigger ‘host’ molecule that allows easy reversible coordination of smaller molecules it interacts with.
A molecule that has been envisioned for such supramolecular chemistry is Tröger’s base, which has a unique V-shaped structure and if several of these V-shaped molecules are connected together, we can think of applications such as catalysis. A catalyst is a molecule that helps the reaction to proceed faster by, for example stabilising their intermediates or bringing the molecular components closer together. Such catalysis, where different molecules end up in the V-shaped cavities and therefore get brought closer together to help the reaction between the components, we can call bi-molecular catalysis. Of course, many more interesting applications could also be possible.
In the Wärnmark group, research has been performed on the linear fusion of Tröger’s base analogues, where it was seen that when fusing these V-shaped molecules together, either a tubular structure or a zigzag shaped compound is formed. The particular compounds studied in this project show the formation of a zigzag shaped linearly fused Tröger’s base analogue. A previously designed and performed synthesis was partially repeated in this project, with the ultimate goal to produce a linearly fused Tröger’s base analogue consisting of 7 sub-units through a multi-step synthesis, which means different reactions are performed to get from one intermediate to the next. (Less)
Please use this url to cite or link to this publication:
http://lup.lub.lu.se/student-papers/record/8946255
- author
- de Groot, Lisa LU
- supervisor
- organization
- course
- KEMR31 20181
- year
- 2018
- type
- H2 - Master's Degree (Two Years)
- subject
- keywords
- organic chemistry, organisk kemi
- language
- English
- id
- 8946255
- date added to LUP
- 2018-06-20 16:09:44
- date last changed
- 2018-06-20 16:09:44
@misc{8946255,
abstract = {{The Tröger’s base molecule has a unique V-shaped cavity and can be fused together in a linear fashion to create either tubular structures or zigzag structures. These structures could be applicable in for example catalysis. The Tröger’s base scaffold is easily functionalised with different side-groups and therefore has a wide range of applications.
Previous research in the Wärnmark group had led to a thirteen-step synthesis from 4-bromo-3-methylaniline to a linearly fused heptakis-TB analogue with methoxy side-groups. The aim of this project was to repeat this synthetic route and to improve it where possible. Also, characterisations of the synthesised compounds have been provided.
This research covers the first nine steps of the synthesis and includes a wide range of reactions, such as electrophilic aromatic substitutions, condensations, a Buchwald-Hartwig amination, a TMS and TFAA protection, and formation and separation of diastereomers.}},
author = {{de Groot, Lisa}},
language = {{eng}},
note = {{Student Paper}},
title = {{Synthesis of Linearly Fused Tröger’s Base Analogues}},
year = {{2018}},
}