Synthesis of Linearly Fused Tröger’s Base
(2018) KEML11 20172Department of Chemistry
- Abstract
- Synthesis of linearly fused heptakis-Tröger’s base has been completed, following a 12 step reaction route. Additionally, characterizations of reaction intermediates have been completed, while sufficient amount of material of different reaction intermediates is available for the characterizations that remain. Tröger’s Base, with predetermined substitution pattern was formed, functionalization of the benzylic position in the diazocine bridge, with (R)-menthyl ester groups, made separation of diastereomeric Tröger’s base analogues possible. Route b, with a bulkier ester side chain, was progressed through, with desymmetrisation followed by condensation to obtain the tris-Tröger’s Base and eventually the heptakis-Tröger’s Base. At the end of... (More)
- Synthesis of linearly fused heptakis-Tröger’s base has been completed, following a 12 step reaction route. Additionally, characterizations of reaction intermediates have been completed, while sufficient amount of material of different reaction intermediates is available for the characterizations that remain. Tröger’s Base, with predetermined substitution pattern was formed, functionalization of the benzylic position in the diazocine bridge, with (R)-menthyl ester groups, made separation of diastereomeric Tröger’s base analogues possible. Route b, with a bulkier ester side chain, was progressed through, with desymmetrisation followed by condensation to obtain the tris-Tröger’s Base and eventually the heptakis-Tröger’s Base. At the end of this project full characterization of heptakis-Tröger’s Base and its reaction intermediates is significantly closer to being available. (Less)
- Popular Abstract
- Atoms within a molecule are normally bound to each other through covalent bonds which can be described as the sharing of two electrons between the two atoms. The focus of supramolecular chemistry can in light of this be described as the study of two molecular components which are bound to each other through forces weaker than this. This binding can happen for example through hydrogen bonding, Π-Π interactions, metal coordination and van der Waals forces.
An interesting molecule which might be useful in supramolecular chemistry is Tröger’s Base (TB). The unique structure of TB, which it owns to its two aromatic rings being fused to a bicyclic diazocine unit, projects it as an V-shaped structure with an electron rich cavity due to the two... (More) - Atoms within a molecule are normally bound to each other through covalent bonds which can be described as the sharing of two electrons between the two atoms. The focus of supramolecular chemistry can in light of this be described as the study of two molecular components which are bound to each other through forces weaker than this. This binding can happen for example through hydrogen bonding, Π-Π interactions, metal coordination and van der Waals forces.
An interesting molecule which might be useful in supramolecular chemistry is Tröger’s Base (TB). The unique structure of TB, which it owns to its two aromatic rings being fused to a bicyclic diazocine unit, projects it as an V-shaped structure with an electron rich cavity due to the two aromatic rings being positioned nearly perpendicular to each other. In addition to this, the two nitrogen’s of the bicyclic unit are linked to each other through a carbon bridge preventing inversion of the molecule. These properties of TB show great promise for a wide range of supramolecular applications.
The focus of this thesis has been to synthesize a linearly fused oligo-TB in order to explore applications of such a construct. Particular applications as potential nanotube was envisioned for the linear heptakis-TB, which was the ultimate goal of the project. If this was to be achieved then one of the applications might be provided by the electron rich inside of the nanotube which might be good electron conductor in electrical devices.
Synthesis followed procedures developed within the group, route was started with the formation of TB by condensation of appropriately substituted anilines to give TB with a predetermined substitution pattern. Functionalization of TB followed by a controlled condensation gave the tris-TB and eventually the desired heptakis-TB. (Less)
Please use this url to cite or link to this publication:
http://lup.lub.lu.se/student-papers/record/8934672
- author
- Sjörén, Aleksander LU
- supervisor
- organization
- course
- KEML11 20172
- year
- 2018
- type
- M2 - Bachelor Degree
- subject
- keywords
- organic chemistry, organisk kemi
- language
- English
- id
- 8934672
- date added to LUP
- 2018-02-19 15:01:16
- date last changed
- 2018-02-19 15:01:16
@misc{8934672,
abstract = {{Synthesis of linearly fused heptakis-Tröger’s base has been completed, following a 12 step reaction route. Additionally, characterizations of reaction intermediates have been completed, while sufficient amount of material of different reaction intermediates is available for the characterizations that remain. Tröger’s Base, with predetermined substitution pattern was formed, functionalization of the benzylic position in the diazocine bridge, with (R)-menthyl ester groups, made separation of diastereomeric Tröger’s base analogues possible. Route b, with a bulkier ester side chain, was progressed through, with desymmetrisation followed by condensation to obtain the tris-Tröger’s Base and eventually the heptakis-Tröger’s Base. At the end of this project full characterization of heptakis-Tröger’s Base and its reaction intermediates is significantly closer to being available.}},
author = {{Sjörén, Aleksander}},
language = {{eng}},
note = {{Student Paper}},
title = {{Synthesis of Linearly Fused Tröger’s Base}},
year = {{2018}},
}