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Development of Surface-Compatible Coupling Reactions with Perfluorophenyl Azides
KTH, School of Chemical Science and Engineering (CHE).
2014 (English)Independent thesis Advanced level (degree of Master (Two Years)), 20 credits / 30 HE creditsStudent thesisAlternative title
Utveckling av ytkompatibla kopplingsreaktioner med perfluorfenylazider (Swedish)
Abstract [en]

This thesis mainly concerned the development of chemical functionalization at nanomaterial surfaces. Perfluorophenyl azide (PFPA) derivatives are known to be versatile photo-coupling agents used in functionalization in surface chemistry. Inspiring by recent interest in thioacid-azide amidation reaction, PFPA in the form was explored in this thesis for surface coupling applications. PFPA-thioacid ligation displayed many characteristics of click chemistry: high yield, good chemoselectivity, high kinetics, metal-free and water compatible reaction. This indicates the potential of it for functioning of various targets. This system was then extended, to start from the rich carboxylic group compounds, due to the scarcity of thioacid moiety in ligands. NHS/DCC/DMAP was found to catalyze transformation of thioacid moiety from carboxylic acid moiety efficiently, which in situ reacted with perfluorophenyl azides. To the best, the one-pot strategy can reach 70% yield of coupling product, within several hours (only trace amount of by-product formation). These results indicate the potential of PFPAs-thioacid reaction as a new type of coupling reactions, for modification and immobilization of molecules.

 

Place, publisher, year, edition, pages
2014.
Keyword [en]
surface functionalization, perfluorophenyl azide, click reaction, thioacid, amidation
National Category
Engineering and Technology
Identifiers
URN: urn:nbn:se:kth:diva-158871OAI: oai:DiVA.org:kth-158871DiVA: diva2:779108
Available from: 2015-01-12 Created: 2015-01-12 Last updated: 2017-08-30Bibliographically approved

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