Show simple item record

dc.contributor.authorLee, Dianneen
dc.date.accessioned2020-05-14T14:53:10Z
dc.date.available2020-05-14T14:53:10Z
dc.identifier.urihttp://hdl.handle.net/1974/27818
dc.description.abstractN-Heterocyclic carbenes (NHCs) have been shown to be exceptional ligands for molecular coordination chemistry due to their ability to form strong carbon-metal bonds. Only recent, our group and others have demonstrated that the strong carbon-metal bonding properties of NHCs can be leveraged for materials chemistry. In 2014, Crudden and co-workers showed that self-assembled monolayers (SAMs) derived from NHCs on gold surfaces were significantly more stable than thiolate SAMs; which, for decades, have been considered the state-of-the-art in SAM chemistry. Since then, our group has continued to advance the field by incorporating unique functionalities to NHCs and new methods of SAM formation. In addition, stability of NHCs in different chemical and electrochemical conditions was critical to determine NHCs use in biological and industrial applications. In this thesis, I will present the use of electrochemical measurement of NHCs in phosphate buffer are discussed to confirm the prospective use of NHC-based SAMs in biological applications. The electrochemical stability of NHC-based SAMs at different levels of applied potential will also be presented. This study is crucial to employ NHC-based SAMs in electrochemical devices such as fuel cells, sensors, and catalysts. For both projects, 5-((6-ferrocenohexyl)oxy)-1,3-diisopropyl-1H-benzo[d]imidazole-3-ium bicarbonate (2-8•H2CO3) and 2-(6-(4-anthraquinyl)-1H-1,2,3-triazol-1-yl)hexyloxy)-1,3-diisopropyl-1H-benzo[d]imidazole-3-ium bicarbonate (8-4•H2CO3) were synthesized as a new NHC-based electrochemical tag molecules to compare with the known NHC 5-((12-(4-(ferrocenyl)-1H-1,2,3-triazol-1-yl)dodecyl)oxy)-1,3-diisopropyl-1H-benzo[d]imidazole-3-ium bicarbonate (1-20•H2CO3) which was previously used in the Crudden lab for electrochemical analysis. The capability of 3-6-ethyl-1,3-diisopropyl-1H-benzo[d]imidazole-5-carboxylate trifluorosulfonate (2-18•OTf) as a measles biosensor will be discussed. The mechanisms of SAM formation with NHCs will be discussed using free carbenes and their precursor bicarbonate and triflate salts. Finally, the first example of NHC depositions on Vulcan xc-72 carbon will be presented, and the effect of different oxidative treatments of carbon to facilitate NHC deposition will be discussed.en
dc.language.isoengen
dc.relation.ispartofseriesCanadian thesesen
dc.rightsQueen's University's Thesis/Dissertation Non-Exclusive License for Deposit to QSpace and Library and Archives Canadaen
dc.rightsProQuest PhD and Master's Theses International Dissemination Agreementen
dc.rightsIntellectual Property Guidelines at Queen's Universityen
dc.rightsCopying and Preserving Your Thesisen
dc.rightsThis publication is made available by the authority of the copyright owner solely for the purpose of private study and research and may not be copied or reproduced except as permitted by the copyright laws without written authority from the copyright owner.en
dc.subjectOrganic Chemistryen
dc.subjectSurface Chemistryen
dc.subjectMaterial Chemistryen
dc.subjectElectrochemistryen
dc.titleN-Heterocyclic Carbene as Self-Assembled Monolayers on Gold and Carbonen
dc.typethesisen
dc.description.degreeM.Sc.en
dc.contributor.supervisorCrudden, Cathleen
dc.contributor.departmentChemistryen
dc.embargo.termsI would like to protect the content of my thesis for a patent that may rise from this researchen
dc.embargo.liftdate2025-05-13T03:53:01Z
dc.embargo.liftdate2025-05-13T14:54:25Z
dc.degree.grantorQueen's University at Kingstonen


Files in this item

Thumbnail

This item appears in the following Collection(s)

Show simple item record