Change search
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • harvard1
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Other style
More styles
Language
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Other locale
More languages
Output format
  • html
  • text
  • asciidoc
  • rtf
Multifunctional Dendritic Scaffolds: Synthesis, Characterization and Potential applications
KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Coating Technology.
2013 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

The development of materials for advanced applications requires innovative macromolecules with well-defined structures and the inherent ability to be tailored in a straightforward manner. Dendrimers, being a subgroup of the dendritic polymer family, possess properties which fulfill such demands. They have a highly branched architecture with a high number of functional groups and are one of the most well-defined types of macromolecules ever synthesized. However, despite their well-defined nature and high functional density, traditional dendrimers commonly lack diverse chemical functionalities. Therefore, this thesis focuses on the synthesis of more complex dendritic materials to extend their tailoring capacity by introduction of dualfunctionalities for multipurpose actions. It covers the synthesis of dualfunctional dendrimers, dendritic modification of linear poly(ethylene glycol) polymers and cellulose surfaces, and the synthesis of linear dendritic hybrids. The building blocks enabling this synthesis, AB2C monomers, were also developed during this work. The orthogonal nature between click groups (azide, alkyne and alkene) and hydroxyl groups have efficiently been utilized for postfunctionalization by robust click chemistry and traditional esterification reactions. Furthermore, linear dendritic hybrids were synthesized, merging the properties of linear and dendritic macromolecules. The dendritic frameworks were tailored towards the production of bone fracture adhesives, novel biofunctional dendritic hydrogels, biosensors and micellar drug delivery vehicles.

Abstract [sv]

Utveckling av material för avancerade applikationer kräver innovativa makromolekyler med väldefinierade strukturer och som kan skräddarsys på ett enkelt sätt. Dendrimerer är en undergrupp av dendritiska polymerer vars egenskaper uppfyller dessa krav. De har en mycket förgrenad arkitektur med många funktionella grupper och är en av de mest väldefinierade befintliga syntetiska makromolekylerna. Trots dess väldefinierade karaktär och höga funktionalitet saknar ofta traditionella dendrimerer multipla kemiska funktionaliteter. Denna avhandling fokuserar därför på syntesen av mer komplexa dendritiska material för att förbättra deras kapacitet att skräddarsys, detta görs genom att introducera fler funktionaliteter som kan utnyttjas för multipla ändamål . Avhandlingen redogör för syntesen av difunktionella dendrimerer, dendritiska modifikationer av polyetylenglykol och cellulosaytor samt syntes av traditionella dendritiska hybrider. Byggstenarna som möjliggör syntesen, AB2C monomerer, framställdes också under detta arbete. Den ortogonala karaktären mellan klick grupper (azid, alkyn och alkene) och hydroxylgrupper har utnyttjats effektivt för funktionaliseringar genom användande av robust ”Click”-kemi och traditionella esterifikationsreaktioner. Vidare tillverkades de linjära dendritiska hybrider för att kombinera egenskaperna hos både linjära och traditionella dendritiska polymerer i en och samma makromolekyl. Samtliga dendritiska strukturer skräddarsyddes för applikationer så som benlimmer, biofunktionella dendritiska hydrogeler, biosensorer och läkemedels-bärande miceller.

Place, publisher, year, edition, pages
Stockholm: KTH Royal Institute of Technology, 2013. , 87 p.
Series
Trita-CHE-Report, ISSN 1654-1081 ; 2013:32
Keyword [en]
Dendrimer, AB2C monomer, Click chemistry, CuAAC, thiol-ene coupling chemistry, TEC, linear dendritic hybrids, micelle, hydrogel, bone adhesive
National Category
Polymer Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-127429ISBN: 978-91-7501-817-1 (print)OAI: oai:DiVA.org:kth-127429DiVA: diva2:644266
Public defence
2013-09-20, Sal F3, Lindstedtsvägen 26, KTH, Stockholm, 10:00 (English)
Opponent
Supervisors
Note

QC 20130830

Available from: 2013-08-30 Created: 2013-08-29 Last updated: 2013-08-30Bibliographically approved
List of papers
1. Bifunctional Dendrimers: From Robust Synthesis and Accelerated One-Pot Postfunctionalization Strategy to Potential Applications
Open this publication in new window or tab >>Bifunctional Dendrimers: From Robust Synthesis and Accelerated One-Pot Postfunctionalization Strategy to Potential Applications
Show others...
2009 (English)In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 48, no 12, 2126-2130 p.Article in journal (Refereed) Published
Keyword
click chemistry, dendrimers, gels, nanoparticles, synthetic methods, phosphorus-containing dendrimers, dendritic macromolecules, click, chemistry, rapid synthesis, terminal alkynes, polymers, architectures, molecules, growth, azides
National Category
Polymer Technologies
Identifiers
urn:nbn:se:kth:diva-18270 (URN)10.1002/anie.200804987 (DOI)000264411800015 ()2-s2.0-61949478182 (Scopus ID)
Note

QC 20100525

Available from: 2010-08-05 Created: 2010-08-05 Last updated: 2017-12-12Bibliographically approved
2. Bifunctional Dendronized Cellulose Surfaces as Biosensors
Open this publication in new window or tab >>Bifunctional Dendronized Cellulose Surfaces as Biosensors
Show others...
2011 (English)In: Biomacromolecules, ISSN 1525-7797, E-ISSN 1526-4602, Vol. 12, no 6, 2114-2125 p.Article in journal (Refereed) Published
Abstract [en]

Well-defined dendronized cellulose substrates displaying multiple representations of dual-functionality were constructed by taking advantage of the efficiency of the click reaction combined with traditional anhydride chemistry. First, activated cellulose surfaces were decorated with several generations of dendrons, and their peripheral reactive groups were subsequently reacted with a trifunctional orthogonal monomer. The generated substrate tool box was successfully explored by accurately tuning the surface function using a versatile orthogonal dual postfunctionalization approach. In general, the reactions were monitored by using a click-dye reagent or a quartz crystal microbalance (QCM) technique, and the resulting surfaces were well-characterized using XPS, and contact angle measurements. Utilizing this approach two different surfaces have been obtained; that is, triethylenglycol oligomers and amoxicillin molecules were efficiently introduced to the dendritic surface. As a second example, mannose-decorated hydroxyl functional surfaces illustrated their potential as biosensors by multivalent detection of lectin protein at concentration as low as 5 nM.

Keyword
CLICK-CHEMISTRY, EFFICIENT SYNTHESIS, FUTURE-DIRECTIONS, DENDRIMERS, AZIDE, FILMS
National Category
Chemical Sciences
Identifiers
urn:nbn:se:kth:diva-35633 (URN)10.1021/bm200201y (DOI)000291499900019 ()2-s2.0-79958779836 (Scopus ID)
Funder
Swedish Research Council, 2006-3617Swedish Research Council, 2009-3259
Note
QC 20110704Available from: 2011-07-04 Created: 2011-07-04 Last updated: 2017-12-11Bibliographically approved
3. Dual-purpose PEG scaffolds for the preparation of soft and biofunctional hydrogels: the convergence between CuAAC and thiol-ene reactions
Open this publication in new window or tab >>Dual-purpose PEG scaffolds for the preparation of soft and biofunctional hydrogels: the convergence between CuAAC and thiol-ene reactions
Show others...
2013 (English)In: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, Vol. 49, no 62, 6938-6940 p.Article in journal (Refereed) Published
Abstract [en]

Orthogonally functionalized PEGs displaying alkenes and azides have been prepared and their dual-purpose scaffolding potential was exploited via click chemistry for controlled insertion of bio-relevant moieties as well as facile fabrication of soft, non-toxic and degradable hydrogels.

National Category
Chemical Sciences
Identifiers
urn:nbn:se:kth:diva-125778 (URN)10.1039/c3cc42084a (DOI)000321576000002 ()2-s2.0-84882247505 (Scopus ID)
Funder
VinnovaSwedish Research Council, 2011-5358 2010-453
Note

QC 20130814

Available from: 2013-08-14 Created: 2013-08-13 Last updated: 2017-12-06Bibliographically approved
4. Multipurpose heterofunctional dendritic scaffolds as crosslinkers towards functional soft hydrogels and implant adhesives in bone fracture applications
Open this publication in new window or tab >>Multipurpose heterofunctional dendritic scaffolds as crosslinkers towards functional soft hydrogels and implant adhesives in bone fracture applications
Show others...
2013 (English)In: Journal of Materials Chemistry B, ISSN 2050-7518, Vol. 1, no 44, 6015-6019 p.Article in journal (Refereed) Published
Abstract [en]

Two sets of heterofunctional dendritic frameworks displaying an inversed and exact number of ene and azide groups have successfully been synthesized and post-functionalized with biorelevant molecules. Their facile scaffolding ability enabled the fabrication of soft and azide functional dendritic hydrogels with modulus close to muscle tissue. The dendritic scaffolds are furthermore shown to be promising primers for the development of novel bone fracture stabilization adhesives with shear strengths succeeding commercial Histroacryl (R).

Keyword
Azide group, Bone fracture, Cross-linkers, Muscle tissues
National Category
Chemical Sciences
Identifiers
urn:nbn:se:kth:diva-127460 (URN)10.1039/c3tb21061h (DOI)000326244900001 ()2-s2.0-84886628793 (Scopus ID)
Funder
Knut and Alice Wallenberg Foundation, 2012-0196Swedish Research Council, 2011-5358 2010-453
Note

QC 20131128. Updated from manuscript to article in journal.

Available from: 2013-08-30 Created: 2013-08-30 Last updated: 2014-01-16Bibliographically approved
5. Side-by-side comparison of dendritic-linear hybrids and their hyperbranched analogs as micellar carriers of chemotherapeutics
Open this publication in new window or tab >>Side-by-side comparison of dendritic-linear hybrids and their hyperbranched analogs as micellar carriers of chemotherapeutics
Show others...
2013 (English)In: Journal of Polymer Science Part A: Polymer Chemistry, ISSN 0887-624X, E-ISSN 1099-0518, Vol. 51, no 19, 3992-3996 p.Article in journal (Refereed) Published
Abstract [en]

Amphiphilic block copolymers are successfully synthesized possessing a hydrophobic dendritic component based on the bis-MPA monomer and a hydrophilic linear polyethylene glycol (PEG) component. The hybrids were either conjured in small scale using robust click reactions between perfect dendrons and linear PEG or multigram polycondensation of hyperbranched blocks from PEG. In all cases, the amphiphiles were assembled to micelles, were found nontoxic and successfully loaded with the chemotherapeutic doxorubicin.

Keyword
amphiphilic, biocompatibility, 2, 2-bis(hydroxymethyl)propionic acid, bis-MPA, block copolymers, click chemistry, dendritic-linear hybrids, drug delivery, micelles, synthesis
National Category
Polymer Chemistry
Identifiers
urn:nbn:se:kth:diva-127462 (URN)10.1002/pola.26825 (DOI)000323654300002 ()2-s2.0-84883208788 (Scopus ID)
Funder
VinnovaSwedish Research Council, 2011-3720 2010-453 2009-3259
Note

QC 20131004

Available from: 2013-08-30 Created: 2013-08-30 Last updated: 2017-12-06Bibliographically approved

Open Access in DiVA

fulltext(15970 kB)387 downloads
File information
File name FULLTEXT01.pdfFile size 15970 kBChecksum SHA-512
5f897fe5693fb3bedf86b9d76b9abd8139cdb4332bf5f1d1b18e5001c3c358a2d9f6334dfd5a853f31a4c02db56fba5e29052341e0c844de31c228bb50ff210b
Type fulltextMimetype application/pdf

Search in DiVA

By author/editor
Hed, Yvonne
By organisation
Coating Technology
Polymer Chemistry

Search outside of DiVA

GoogleGoogle Scholar
Total: 387 downloads
The number of downloads is the sum of all downloads of full texts. It may include eg previous versions that are now no longer available

isbn
urn-nbn

Altmetric score

isbn
urn-nbn
Total: 288 hits
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • harvard1
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Other style
More styles
Language
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Other locale
More languages
Output format
  • html
  • text
  • asciidoc
  • rtf