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Rapid, regioselective deuteration of dimethyl-2,2'-bipyridines via microwave-assistance
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.ORCID iD: 0000-0003-2865-2513
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
2015 (English)In: RSC Advances, ISSN 2046-2069, E-ISSN 2046-2069, Vol. 5, 2684-2688 p.Article in journal (Refereed) Published
Abstract [en]

Isotopically pure [D6]-dimethyl-2,2′-bipyridine derivatives were selectively and rapidly formed using microwave-assisted regioselective deuteration of the methyl moieties of the parent bipyridine in a deuterium oxide solution. For instance, [D6]-4,4′-dimethyl-2,2′-bipyridine was formed in quantitative yield within 15 minutes, in a simple and convenient process.

Place, publisher, year, edition, pages
Royal Society of Chemistry, 2015. Vol. 5, 2684-2688 p.
Keyword [en]
Deuteration, Microwave irradiation, bipyridine
National Category
Organic Chemistry
Research subject
Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-176923DOI: 10.1039/C4RA13397HISI: 000346188400043Scopus ID: 2-s2.0-84916899627OAI: oai:DiVA.org:kth-176923DiVA: diva2:869059
Funder
EU, FP7, Seventh Framework Programme, KDHH B61632
Note

QC 20151119

Available from: 2015-11-12 Created: 2015-11-12 Last updated: 2017-12-01Bibliographically approved
In thesis
1. Synthesis and Applications of Dynamic Multivalent Nanostructures
Open this publication in new window or tab >>Synthesis and Applications of Dynamic Multivalent Nanostructures
2015 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

This thesis focuses on the design, synthesis and development of dynamic multivalent nanostructures such as supramolecular dendrimers, liposomes and gold-functionalized nanostructures. These structures can be used for drug delivery and molecular sensing applications. This thesis is divided into three parts:

In part one, a general introduction to self-assembly, dynamic systems, metalligand exchange, nanostructured dendritic scaffolds, liposomes and gold nanostructures is given.

In part two, a microwave approach is presented as an efficient method for the regioselective deuteration of bipyridine scaffolds. Dynamic systems based on transition metal-bipyridine coordination complexes were investigated. The compositional self-adaptation and kinetics of these dynamic systems were successfully assessed by ESI-MS. Based on this amphiphilic dendrimers/metallodendrimers were also designed and synthesized via  a convergent strategy. Their ability to self-assemble into supramolecular assemblies and their controlled disassembly was effectively demonstrated.

In part three, two types of drug delivery systems based on dynamic multivalent nanostructures of glycodendrimers/metalloglycodendrimers and drugpresenting liposomes were developed. The dynamic self-assembly of these architectures into supramolecular nanostructures with site-specific functionality through interacting carbohydrate or cholesterol moieties was assessed. The host-guest interaction/encapsulation and controlled release with external stimuli were studied using a fluorescent probe, as well as selected drug molecules. The antibacterial property of the drug delivery systems was also evaluated, demonstrating an enhanced bactericidal activity. A new, rapid and simple approach for the functionalization of plasmonic gold nanostructured surfaces was also developed. The optical performance and light-specific sensitivity of the fluorescent probe on the resulting nanostructures were also presented.

Place, publisher, year, edition, pages
Stockholm: KTH Royal Institute of Technology, 2015. 80 p.
Series
TRITA-CHE-Report, ISSN 1654-1081 ; 2015:43
Keyword
multivalent nanostructures, self-assembly, metal-ligand exchange, dynamic covalent chemistry, bipyridine derivatives, dendrimers, liposomes, drug delivery, antimicrobial materials, fluorescent probe, plasmonic chemistry, gold surface functionalization
National Category
Nano Technology Organic Chemistry
Research subject
Chemistry
Identifiers
urn:nbn:se:kth:diva-177280 (URN)978-91-7595-662-6 (ISBN)
Public defence
2015-12-11, F3, Lindstedtsvägen 26, KTH, Stockholm, 14:00 (English)
Opponent
Supervisors
Funder
EU, FP7, Seventh Framework Programme, KDHH B61632
Note

QC 20151119

Available from: 2015-11-19 Created: 2015-11-17 Last updated: 2015-11-19Bibliographically approved

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Publisher's full textScopushttp://pubs.rsc.org/en/Content/ArticleLanding/2015/RA/c4ra13397h#!divAbstract

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Neranon, Kitjanit

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