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Synthesis of a rotaxane with switchable lanthanide luminescence
KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.
2022 (English)Independent thesis Advanced level (degree of Master (Two Years)), 20 credits / 30 HE creditsStudent thesisAlternative title
Syntes av en rotaxan med modifierbar lantanidluminescens (Swedish)
Abstract [sv]

I rotaxaner följs förflyttningen av makrocykeln vanligtvis med 1H-NMR spektroskopi. Målet med detta projekt är i stället att utveckla ett system som möjliggör att förflyttningen av makrocykeln kan observeras med hjälp av luminiscerande lantanid emission. Detta bör vara ett kraftfullt verktyg, då luminiscerande emission skulle möjliggöra att makrocykelns position längs med tråden kan avläsas direkt med blotta ögat. För att lantanid-baserade system ska kunna luminiscera krävs det att en aktiverande antennmolekyl finns i närheten av lantaniden. I detta projekt placerades en lantanidligand i den ena stoppande änden av en [2]rotaxan och en antennmolekyl sattes på den trådade makrocykeln. En förändring av pH:t medför att makrocykeln förflyttas närmre till lantanidliganden, vilket i sin tur medför att antennen aktiverar lantaniden och den luminiscerande emissionen startar. Baserat på styrkan av luminiscensen bör man då kunna avgöra makrocykelns position i rotaxanen. I framtiden hoppas vi kunna använda detta visualiseringsverktyg för att kunna börja använda rotaxaner som biosensorer för medicinsk diagnostik.

Abstract [en]

In rotaxanes, the movement of the macrocycle is usually tracked using 1H-NMR spectroscopy. The goal of this project is to instead develop systems so one can follow the macrocycle movement through luminescent lanthanide emission. This should be a powerful tool, as luminescence emission would allow for a direct visual readout of the macrocycle position along the thread with the naked eye. To allow luminescence in lanthanide-based systems, a sensitizing antenna molecule needs to be present in close proximity to the lanthanide. In this project, a lanthanide ligand was placed at the stoppered end of a [2]rotaxane, and a sensitizing antenna was attached to the threaded macrocycle. A change in pH induces the macrocycle to move closer to the lanthanide stopper, which causes the antenna to sensitize the lanthanide and start the luminescence emission. Based on the strength of the luminescence, one should then be able to determine the location of the macrocycle in the rotaxane. We hope to use this visual readout tool to eventually turn rotaxanes into useful point-of-care biosensors for medical diagnostics.

Place, publisher, year, edition, pages
2022.
Series
TRITA-CBH-GRU ; 2022:161
Keywords [en]
mechanically interlocked molecules, supramolecular chemistry, luminescence, rotaxanes, lanthanides
Keywords [sv]
mekaniskt sammankopplade molekyler, supramolekylär kemi, luminescens, rotaxaner, lantanider
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-315958OAI: oai:DiVA.org:kth-315958DiVA, id: diva2:1685128
Subject / course
Chemical Science and Engineering
Educational program
Degree of Master - Molecular Science and Engineering
Supervisors
Examiners
Available from: 2022-09-24 Created: 2022-08-01

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