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Development of synthetic methodology for non-symmetric fullerene dimers
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC. (Helena Grennberg)
2019 (English)Independent thesis Basic level (degree of Bachelor), 10 credits / 15 HE creditsStudent thesis
Abstract [en]

This bachelor thesis covers the initial development of a synthesis of fullerene dimers using two different types of linking reactions. Different setups for [3+2] cycloadditions to fullerenes (Prato reaction) were tested, and for that purpose, an N-alkylated amino acid was synthesised. Hydroarylation of fullerene using Rh-catalysis was also studied, using both MIDA protected and unprotected boronic acids, as well as by using cycloaddition products. A range of model compounds in form of fulleropyrrolidenes were synthesised. Products were puried with HPLC and analysed with MALDI-MS and 1H NMR. A range of new compounds were synthesised and characterisation of them was begun. With MALDI-MS, indications that the fullerene dimer had formed were found. Using synthesised model compounds, by-products of the hydroarylation reaction were identied.

Abstract [sv]

Denna kandidatuppsats behandlar påborjandet av syntesutvecklingen för bildandet av fullerendimerer genom användandet av två olika sorters länkningskemi. Olika förhållanden och reagens for [3+2]-cykloaddition till fullerener (Pratoreaktionen) studerades, och i samband med det syntetiserades en N-alkylerad aminosyra. Hydroarylering av fullerener med hjälp utav rodiumkatalys studerades även, genom reaktioner med både skyddade och oskyddade borsyror, inklusive fulleropyrrolidiner. Produkter har renats upp med HPLC och analyserats med MALDI-MS och 1H NMR. En uppsättning nya substanser har syntetiserts, men karaktäriseringen av dessa har inte slutförts. Genom användning av MALDI-MS har indikationer att fullerendimer bildats framkommit. Genom att använda syntetiserade modellsubstanser har biprodukter från hydroaryleringsreaktionen identierats.

Place, publisher, year, edition, pages
2019. , p. 49
Series
UPKEM C ; 138
Keywords [en]
fullerene, dumbbell, Prato, rhodium catalysis, fullerene dimer, HPLC, amino acid, cyclo addition, alkylation, solubility
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:uu:diva-386047OAI: oai:DiVA.org:uu-386047DiVA, id: diva2:1329487
Subject / course
Chemistry
Educational program
Bachelor Programme in Chemistry
Supervisors
Examiners
Available from: 2019-07-02 Created: 2019-06-24 Last updated: 2019-07-02Bibliographically approved

Open Access in DiVA

The full text will be freely available from 2021-06-01 16:28
Available from 2021-06-01 16:28

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