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Synthesis and aggregation-induced emission of novel ciprofloxacin derivatives
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
Syntes och aggregerings-inducerad emission hos nya ciprofloxacin-derivat (Swedish)
Abstract [en]

This thesis deals with the investigation of photo-physical properties and aggregation features of novel derivatives of ciprofloxacin appended with aromatic moieties. These derivatives were synthesized using a novel 1, 3-dipolar cycloaddition reaction. Their photo-physical properties were studied using UV-vis and fluorescence spectroscopy. Emission features were influenced by solvent polarity with broadened peaks in polar solvents. However, solvent polarity did not influence their absorbance features and thus their solvatochromic features were studied. These molecules were found to form nano sized spherical aggregates in high water content solvent mixtures, accompanied with enhanced emission. Investigations using dynamic light scattering (DLS) and transmission electron microscopy (TEM) shed light on those features. Moreover, aggregation-induced emission features in various solvent combination (acetonitrile/water, DMF/water and THF/water mixtures), displayed different behavior. These studies indicated that water played a major role in the formation of aggregates thereby influencing the size and morphology. In addition, X-ray crystal structure highlighted perfluorophenyl/perfluorophenyl interactions, which may play a role in guiding the morphology and contributing to the long term stability of these molecular aggregates.

Application of these derivatives was then explored. As molecular probes, they were found to be able to sense water quantitatively down to ppm levels. Due to their stability and metal binding properties of fluoroquinolones, these fluorescent nano-aggregates were evaluated for their metal binding properties.

Place, publisher, year, edition, pages
2014.
Keyword [en]
Ciprofloxacin, Perfluorophenyl/phenyl, Aggregated-induced emission, Twisted intramolecular charge transfer, Solvatochromic probes.
National Category
Engineering and Technology
Identifiers
URN: urn:nbn:se:kth:diva-158717OAI: oai:DiVA.org:kth-158717DiVA: diva2:778885
Available from: 2015-01-12 Created: 2015-01-12 Last updated: 2017-08-30Bibliographically approved

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  • apa
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  • Other locale
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