Giant macrocycles from fused polynorbornanes

Coomber, Daniel 2021, Giant macrocycles from fused polynorbornanes, B. Science (Hons) thesis, School of Life and Environmental Sciences, Deakin University.

Attached Files
Name Description MIMEType Size Downloads

Title Giant macrocycles from fused polynorbornanes
Author Coomber, Daniel
Institution Deakin University
School School of Life and Environmental Sciences
Faculty Faculty of Science, Engineering and Built Environment
Degree type Honours
Degree name B. Science (Hons)
Thesis advisor Pfeffer, FrederickORCID iD for Pfeffer, Frederick orcid.org/0000-0002-5441-6437
Date submitted 2021-03-30
Keyword(s) covalent organic macrocycle
self-assembly
boronate ester
polynorbornanes
Summary Since the field was first established, the synthesis and application of macrocycles has been a critical aspect of supramolecular chemistry. Indeed the 1987 Nobel Prize in chemistry was awarded in part for the discovery of macrocycles. Of the methods used for the formation of macrocycles, self-assembly through dynamic covalent bond formation/cleavage stands out as an efficient method to access macrocycles through simple, one pot processes.In particular, the formation of boronate esters has been used to construct a number of self-assembled covalent organic macrocycles. Many of these larger structures have been synthesised by combining a catechol species (benzene-1,2-diol) and a boronic acid. It has been shown that norbornane 1,2-diols form more thermodynamically stable boronate esters than those made from catechols yet this approach has never been used for the formation of a larger covalent organic macrocycle.In this project, the assembly of a covalent organic macrocycle from a fused polynorbornane tetraol was performed. Firstly, a tetraol of suitable geometry was designed and subsequently synthesised. Then, the tetraol was reacted with benzene-1,4-di-boronic acid to assemble the overall macrocycle.The outcomes of this project were the successful synthesis and characterisation of both a novel polynorbornane tetraol and novel macrocycle (characterised using 1H, 13C, DOSY, and HRMS). These results confirm the validity of this new approach and it is expected that this method can be used for the synthesis of a wide range of covalent organic structures.
Language eng
Indigenous content off
Field of Research 3403 Macromolecular and materials chemistry
Description of original 83 p.
Copyright notice ©All rights reserved
Persistent URL http://hdl.handle.net/10536/DRO/DU:30150529

Connect to link resolver
 
Unless expressly stated otherwise, the copyright for items in DRO is owned by the author, with all rights reserved.

Versions
Version Filter Type
Citation counts: TR Web of Science Citation Count  Cited 0 times in TR Web of Science
Scopus Citation Count Cited 0 times in Scopus
Google Scholar Search Google Scholar
Access Statistics: 18 Abstract Views, 0 File Downloads  -  Detailed Statistics
Created: Fri, 30 Apr 2021, 15:01:07 EST by Bernadette Admin Houghton

Every reasonable effort has been made to ensure that permission has been obtained for items included in DRO. If you believe that your rights have been infringed by this repository, please contact drosupport@deakin.edu.au.